0:00

A quick heads up this episode contains some strong language adult situations and some seriously douchey behavior by a certain male singer Whose

0:09

name rhymes with mayor.

0:11

Listener discretion is advised.

0:22

It's the summer of 2006.

0:23

Jessica and her mother, Tina are in a cavernous fashion showroom in New York city.

0:30

They're watching a parade of models, saunter around the room, and the moment is a dream come true for both of them.

0:38

That's because all of the models are wearing shoes created for Jessica's new fashion line that Jessica Simpson collection and this collection is for real everyday women.

0:49

The shoes are affordable, they're Comfortable,

0:51

and they're made for walking.

0:53

Literally One

0:55

of our first products is a pair of bright red leather boots.

0:57

Just like the ones she wore in the video for her head single.

1:01

And they sold out immediately.

1:02

What started as some sketches on a restaurant napkin over lunch with her mom has become real and it turns out Tina Simpson is the perfect partner for this venture.

1:14

The woman just knows how to get shit done.

1:16

There's something about working in fashion that just makes Jessica happy.

1:21

It all comes easily to her.

1:23

She's not stressing about being perfect or thin or a good wife.

1:28

This warehouse full of discount shoes is Jessica.

1:31

Simpson's happy place. But unfortunately the world outside that warehouse is still a complicated, hot mess.

1:41

And so is Jessica's new boyfriend.

1:43

He's obsessed with her.

1:45

He's the smartest person she's ever met before.

1:48

And the sax is amazing.

1:51

Jessica's usual.

1:53

Motto is true, love waits.

1:54

But with this guy, she's all about the try before you buy.

1:58

And those two are constantly trying.

2:01

And when they aren't, they're texting A

2:05

new love how Perfect

2:07

it should be.

2:09

Except that every time Jessica texts bulgy mix smarty pants, she has her assistant proofread it before she hits send he's critical of everything she says and does.

2:20

But he always says it's because he wants her to be her best self.

2:24

Jessica feels like he's so much smarter than her.

2:27

He makes her feel dumb.

2:31

Oh, insert red flag emoji. That's

2:33

what her mom has been trying to tell her.

2:35

But now Tina just rolls her eyes and says, that is a terrible relationship.

2:40

If you have to be scared that you misspelled something, okay, Can

2:45

we call this episode? Tina Simpson is spitting straight facts.

2:49

Oh, just wait a few minutes when Tina's wrong.

2:51

She's wrong hard, but we've got to give credit where it's due because at this exact moment, she's right on the, about this new guy, dude is toxic and Jessica's going to go through hell before she figures that out.

3:07

All right, friends, let's talk dating specifically, dating unmatch.

3:16

American singles have spoken, being hot as out and being emotionally mature is in.

3:22

You heard it here first guys. I mean, it's pretty interesting.

3:25

Listen to this matches. Annual survey found that for the first time in more than a decade, emotional maturity ranks higher than physically attractive on singles priority lists.

3:35

So emotionally mature adults are the new sexy.

3:38

I mean your time to shine, take it from me.

3:40

Yeah. There's nothing hotter than dating someone that thinks running errands together counts as a date.

3:44

So I don't know. Richie's are you ready for something more now is a great time to download match because right now messaging, your top matches is free.

3:52

If you know what you want and you're not afraid to say it, download match today Then

3:57

Mo is a weekly, sometimes daily part of my life from rent and utilities to concert, tickets and dinners out.

4:04

Venmo makes it so easy to share the fun and split the check in the app.

4:07

And next time you split the bill, you can score $10 when you pay with Venmo.

4:12

You heard me ordering delivery for the group.

4:14

Get paid back before your meal arrives, share a ride with your roommate, split the car and the charge.

4:20

And if you sign up today with code Wondery, you'll get $10 to send an spend offer ends December 31st, 2021 limited availability see terms at venmo.me/signup.

4:31

10 that's, $10 with promo code Wondery From

4:44

Wondery. I am Arisha Skidmore Williams and I'm Brooks different.

4:48

And this is even the rich in our last episode, Nick and Jessica's reality showed newlyweds, made Jessica a huge star and left Nick in the dust.

4:58

The fallout wreck their relationship and ended their marriage.

5:01

Now, Jessica is on her own for the first time in her life.

5:06

She's partying a lot and dating her way through Hollywood puppy Heim.

5:11

A good time girl, paparazzi shots.

5:13

Jessica's a woman under a lot of pressure.

5:16

She really needs money after all.

5:19

She's still the family business.

5:20

Jessica promised her dad she'd make back all the money she gave Nick and they're divorced.

5:25

Now she has to figure out how this is episode three, walking in circles.

5:32

It's the summer of 2006.

5:41

And Jessica Simpson is making her way through the loud clanging kitchen of a trendy Soho hotel.

5:50

A bunch of smells hit her nostrils all at once.

5:53

As she walks restaurant trash, coffee grounds and French fries.

6:02

She's on a top secret mission. So she's keeping her head down.

6:06

She's in incognito mode, all black clothing and massive sunglasses.

6:09

But of course there's high heels.

6:12

There's always high heels.

6:15

Jessica's motto is the higher the heel, the, Oh

6:20

God. Okay. Mine is the higher, the heel, the weaker, the ankles, but the, for her Jessica

6:26

steps into the creaky service elevator and rides to the penthouse or excitement level rising with each floor.

6:33

When the elevator stops, the door slides open and she peaks out all clear.

6:41

She gives her hair a sexy shampoo, commercial shakeout that walks to the penthouse store and knock softly three times a second later, he opens the door.

6:53

John Mayer is dark.

6:57

Hair is shaggy and unkempt.

6:59

Just the way Jessica likes it.

7:01

And he's got a look on his face, like he's starving and she's a prime rib.

7:05

She tumbles into his arms and right into his bed.

7:09

The sex is hot and full of passion.

7:12

And when John's not touching her, he's talking about her.

7:16

He's telling her what he loves about her body or about writing songs about it.

7:21

Your body is one of them.

7:23

Yeah, just like that. Although that song actually predates Jessica, but the sentiment definitely applies.

7:30

And Jessica loves how obsessed he is with her.

7:34

He makes her feel seductive and powerful.

7:37

When she gets out of bed to go to the bathroom, he whines, where are you going?

7:43

It's a refreshing change from her ex Nicholas shed.

7:46

By the end of their marriage.

7:48

He barely cared what time zone she was in.

7:51

All right, hold on, back up. How did Jessica even meet this stage?

7:55

Five clinger Phrasing?

7:57

So they met at a Grammy party back when she was still married.

8:01

John started sending her these friendly emails.

8:04

And as soon as Jessica was single key pounds, and then he kept pouncing, they've had a lot of secret.

8:11

Rendezvous is like this on both coasts.

8:13

And when work keeps them apart, John watches, Jessica is proactive infomercials late at night.

8:19

They feel closer to her. I

8:21

guess there's nothing hotter than acne Or

8:25

watching infomercials on repeat.

8:27

Yeah. Back in the Soho hotel room though, the TV is definitely off.

8:33

Jessica and John are still up.

8:35

When the light of the sun starts to stream through the blinds.

8:38

If there's one thing these guys do more than have sex, it's talk only the talking part.

8:44

Isn't quite as good as this ex because it's mostly just John talking.

8:48

John, Mayer's an Olympic level chatterbox.

8:51

He loves to ask provocative questions and challenge Jessica's convictions.

8:56

He loves to say totally supportive, not at all passive aggressive things to her.

9:01

Like I think your true self is so much greater than the person you're settling on.

9:06

Being says, the guy who's jacking off to acne commercials.

9:09

I mean, everyone should get a facial from time to time.

9:13

True. But you have to remember, this is the first time in her life that Jessica's been on her own.

9:18

She's trying to figure out who she is outside of the televised car wreck.

9:23

That was our marriage. So when John tells her, I believe there's a truly great woman inside you just waiting to come out, Jessica grace.

9:32

Now she just has to go out and find her It's Jane 2006 and Jessica Simpson looks like sex on wheels.

9:45

Literally she's in roller skates and dressed in skimpy red shorts and a matching tube.

9:52

Top her feathered, Farrah Fawcett hair, gorgeously frames.

9:55

Her perfectly made up face.

9:57

A harness is wrapped around her waist and attached to a rolling camera cart together.

10:03

She and the cart sail around a San Fernando valley roller rink, all the disco era strains of her new single a public affair Philby air she's filming a music video for her upcoming fifth studio album.

10:16

The roller disco concept was her mom's idea, even though her dad is Jessica's official manager.

10:23

Tina is the one with the most inspired ideas.

10:26

And this video concept is no exception.

10:29

As Jessica rolls around the rink with her famous girlfriends, Christina Applegate, Christina Milian and Eva Longoria.

10:37

She looks like a shining disco doll who doesn't have a care in the world.

10:41

Her ex-husband Nicholas Hayes post-divorce album was a little rough for her.

10:48

It was called what's left of me and featured tracks.

10:51

Like I can't hate you anymore.

10:53

That were clearly about their doomed marriage, but Jessica doesn't feel the need to put anyone down.

11:00

Now, one song on the album is about Nick.

11:03

She just wants to move on. I

11:05

fell in love, really young. You know, people change, we all change and it's okay to change.

11:15

That's Jessica talking to a small studio crowd during an MTV special promoting the album.

11:20

She's sitting on the edge of the stage, answering questions from an all female crowd.

11:24

And she's definitely channeling those late night conversations with Johnny Knoxville.

11:29

She was terrified of change until he told her to embrace it.

11:33

The problem is Johnny was wrong about one thing.

11:37

Change is fucking hard because underneath that confident I got this surface.

11:43

Jessica is barely holding it together.

11:47

When you're going through difficult times, how do you get through?

11:49

Like I say, so this song actually, I was going through a really hard time, a very hard time.

11:58

This was Christmas and I got it.

12:02

I understood it. And

12:05

then she sings the Patty Griffin song, let him fly and totally breaks down crying.

12:09

So while the album keeps shouting, I'm okay.

12:13

Everything's awesome. Let's dance deep down.

12:16

Jessica is scared.

12:17

A public affairs, the first album she's executive producing all on her own.

12:23

No more Tommy Matola telling her what to sing, what to wear or how much he has to weigh.

12:29

She co-wrote 10 of the 13 songs and this is all her vision exciting, but terrifying.

12:36

And it gets even more terrifying when the world responds to the album with a resounding the record sells fine, but Jessica wasn't going for fine.

12:49

She needed this to be a hit, but it turns out the world just isn't that interested in a happy Jessica Simpson, not after she broke up.

12:58

America's favorite couple Johnny Knoxville.

13:01

And Steve-O good point.

13:03

America's second. Favorite couple.

13:05

Besides her work on her fashion line, she's only got one person to help soften the blows captain supportive John Mayer, but this love Fest will end a lot like on a monthly basis because there's one other problem with John Mayer, he keeps breaking up with her It's December of 2006, and Jessica is pacing around a dressing room at the Kennedy center opera house in Washington, DC.

13:36

She's there to sing nine to five at a Dolly Parton tribute.

13:40

It's going to be televised on CBS.

13:42

Jessica is honored to be there and she really wants to do well.

13:47

And not just because her singing career of late, hasn't exactly been stellar.

13:52

She wants to rock this performance because she's going to be singing for Dolly.

13:57

Dolly Parton is Jessica's ultimate role model.

14:00

She's another curvy blonde from the south who everyone underestimated.

14:04

And now she basically rules the school.

14:08

The lineup is full of other A-listers like Reba McEntire, Reese Witherspoon, and Shanaya Twain.

14:16

Jessica really should be hanging in the green room with them, but she's not feeling like an a Lister tonight.

14:23

In fact, she's not leaving the dressing room until she has to, because that's where the whiskey is.

14:29

The night before John Mayer broke up with her again, over email, my God, the night before she's performing at the Kennedy center, Dick move.

14:40

Yeah. He has a knack for timing, these breakups for maximum catastrophic effect.

14:45

And he likes to make them even more dramatic and confusing by attaching MP3s.

14:50

This, he sends the Aerosmith song.

14:53

Angel I'd be like new email who does exactly, but it sent Jessica into this total tailspin.

15:00

So instead of rehearsing, nine to five, Jessica sat up all night going over the lyrics of angel, trying to figure out what John is trying to tell her, is there an answer to what she did wrong?

15:12

Is it because she's not smart enough for him now?

15:16

Jessica is exhausted because she hasn't slept.

15:19

And she feels like she's having a nervous breakdown because she can't get Steven Pilar out of her head, which brings us back to the whiskey.

15:27

She thinks the booze and a lot of it is the only thing that's going to get her through the night.

15:32

Tina and Joe think otherwise they keep telling her you need to not be drinking, but Jessica's like this doesn't make me drunk at all.

15:42

And also why are there six of you guys?

15:44

So Jessica is totally fine and not at all drunk.

15:49

When the phone rings in our dressing room a few minutes before she goes on.

15:52

And of course it's John Mayer.

15:56

The second it becomes clear. He's not calling to apologize and diffuse the situation.

16:01

They start going at it.

16:03

Jessica screams at him.

16:05

How could you do this to me? Why do I have to be thinking of you all the time?

16:10

If you're going to let me go, let me go.

16:13

John hates dealing with her when she's drunk.

16:15

So he just hangs up on her.

16:18

And that's when the reality of her condition hits Jessica.

16:22

She really is totally and completely drunk.

16:24

And Reese Witherspoon really is introducing her to a packed house.

16:29

Jessica is never gone on stage drunk before.

16:32

And yet here she is walking out onto the stage at the Kennedy center.

16:37

She hears her band start playing nine to five.

16:40

Then she hears herself singing along.

16:42

And here's the thing.

16:44

Maybe she could have pulled off a slower power ballad like angel that night, but nine to five is all Dolly that song's got places to be.

16:53

And Jessica can't keep up with it.

16:56

She gets to the lyrics.

16:57

They let you dream just to watch them shatter.

17:00

And she shatters.

17:01

She freezes.

17:03

Oh, no, not again.

17:05

Again, except it's not pre pubescent, Justin Timberlake and the mascot tears watching this time.

17:12

Jessica looks up at the balcony and sees president Barack Obama and first lady Michelle, right next to all of these other dignitaries in black tie.

17:22

Then she locks eyes with Dolly herself.

17:25

Who's looking down at her with grave concern, seeing her idol, right bear before her very eyes shakes Jessica out of her liquor induced stupor.

17:34

She's failing.

17:36

She's not good enough for Dolly.

17:38

So then right in the middle of the performance, Jessica says, I'm so sorry.

17:45

It's an honor to be here, but this song is too good for me.

17:48

Then she walks off stage with a drunken awkward hop.

17:53

After the show, Dolly shows up in her dressing room.

17:58

She's not angry.

18:00

In fact, she gives her a pep talk.

18:03

She slips Jessica her card with a handwritten phone number on the back and tells her if you ever need anything, you call me.

18:11

We Don't deserve Dolly.

18:13

We really don't. And in the meantime, Dolly's like the band's waiting for you.

18:18

Get back out there and do this song and we'll cut it into the show when it airs.

18:22

But when Jessica heads back to the stage and looks out into the ornate empty opera house, she can't do it.

18:30

Not because she's too drunk, but because she's too sad, she feels totally and completely empty.

18:37

It takes all her strength to turn to the band and Pell them.

18:41

I'm sorry for wasting your time.

18:43

Then she walks into the wings or Joe is waiting and tells him I will never sing again.

18:49

It's a decision that will shape the rest of her life.

19:00

So if you've listened to our show for a while, you might have heard us talk about best fiends, one of the best match, three mobile puzzle games out there.

19:07

Can I tell you how glad I've been to have best fiends on my phone throughout all of the holiday madness this year?

19:13

It's the perfect pick me up when I need a break from the chaos, which is often, Oh God, I hear that.

19:19

Yes. So I'm a really big fan of the gameplay.

19:22

It's pretty unique. It's got a really fun storyline.

19:25

It's got collectible fiends that are absolutely adorable.

19:28

And it's got a ton of fun puzzles, which I, of course love.

19:31

They've got literally thousands of levels with more added all the time.

19:35

So there's always a fresh challenge waiting for you.

19:37

And you just need that mental pick me up.

19:39

Yeah. And also traveling and no wifi, no problem.

19:44

You can play best fiends wherever.

19:46

And whenever you want with offline mode comes in handy for all that plane flying.

19:50

So even if your holiday travels have taken you off the beaten bath, you can still play.

19:55

Yeah. Like I, this is one thing when I'm flying these games are my go-to because it's just, I don't know.

20:02

It's fun. It's relaxing. It keeps my mind busy.

20:04

So best ones is perfect for airplane travel.

20:08

Take it from me. I love a good distraction.

20:10

Yeah, you guys can download best fiends free today on the app store or Google play that's friends without the, our best fiends.

20:20

Hi, I'm Kelly Martin to launch a life of creativity.

20:23

You just need a little spark and a big break.

20:27

I'm Chad Lowe on our new podcast series.

20:29

The big break Kelly and I talk with actors and take a deep dive into the magical moments that changed their careers and lives forever.

20:37

In each episode, we'll take our gas back to the very beginning before the starring role, the golden globe nominations, the Tony wins and the adoring fans.

20:45

We'll talk about the stumbles obstacles.

20:47

They faced along the way who influenced them and where they find their inspiration.

20:51

Now The big break goes deeper than typical celebrity interviews.

20:54

Chad and I have been working actors for almost our entire lives.

20:58

We'll reveal the hard work and lucky breaks.

21:00

It takes to become a successful leading actor Because

21:03

for every DiCaprio or Jolie, there are thousands who grinded out every day, making their dreams of a creative life.

21:10

Come true. Join us on the big break, where we explore what it takes to And

21:14

make it follow the big break on apple podcasts, Spotify, Amazon music, or wherever you're listening.

21:19

Now It's

21:27

early 2007 and Jessica Simpson is hanging out backstage at a concert hall in Adelaide, Australia.

21:35

She isn't there to perform.

21:37

She's still reeling from the Kennedy center debacle and she meant it.

21:41

When she told her dad she'd never sing again.

21:44

She's also died. Her signature blonde hair, this dark shade of brown.

21:48

It's her attempt to be anybody other than the drunk mess who closed out 2006 by disappointing Dolly Parton, a president or fans and herself dying.

22:00

Her hair is the easy, fun change she needs right now.

22:04

But it doesn't magically make our problems disappear or get her shitty on again, off again, boyfriend to treat her better.

22:10

In fact, Jessica is here at this concert hall to support her boyfriend, John Mayer.

22:18

Oh my God. What are we up to now?

22:20

Like for on again at this point, something like that.

22:23

But right now, Jessica is craving comfort, social pick what she can get because deep down part of her thinks John is all she deserves.

22:34

But another part of her thinks that she'll never be good enough for him.

22:38

It's all very complicated and a little sad.

22:41

Suffice it to say, Jessica is fine playing groupie on the John Mayer tour bus.

22:46

When a girl working backstage at the venue as sir, when are we going to hear you sing again?

22:52

Jessica lies and says, oh, soon the truth is even if she hadn't recently vowed to stop singing, she'd be scared to make music around.

23:01

John. When she looks at him, she sees a guitar God and a Grammy darling, which just makes her feel even worse.

23:10

Overall. She's not in a good place. It doesn't even register for her that Baca misstates, the Jessica Simpson collection is blowing up.

23:19

She's racking up millions of dollars in sales at department stores like Macy's and Dillard's did you say Macy's just kidding?

23:27

No, that's a really big one for her.

23:30

Yeah. Through all of this John drama and misery, she still scanning the crowd at every concert for inspiration.

23:36

She photographs random people on the street.

23:39

She snaps hundreds of photos to send back to Tina and the design team.

23:43

She wants capture how women in the real world dress, how they like their jeans to fit and where they're crapping their crop tops.

23:51

Jessica even creates lookbooks on the tour bus.

23:55

She and John fall in love with the high-end designer in Japan.

23:59

So Jessica tries to imagine how the spirit of those luxury pieces could be incorporated into items.

24:05

Our regular girl could easily afford thinking about her collection.

24:09

Customers is definitely a bright spot in her life right now, but it's also bittersweet because she's still that girl who just wanted to fit in and be like everybody else.

24:20

And everything else she's dealing with at the moment, feel so far away from that because there is nothing ordinary or regular or understated about John on the tour.

24:31

He really starts to pour it on thick with the grand gestures.

24:34

He buys her a diamond necklace, a Tiffany's.

24:37

He arranges a private tour for them of the Sistine chapel in Rome, but the splashier and fancier, he gets the more uncomfortable and less like herself.

24:48

She feels, then she worries.

24:50

She's just going to disappoint John.

24:51

And on and on and on this rollercoaster is making me nauseous.

24:57

Yeah. You and me both. Jessica's worst fears play out in a loop in her head, 24, 7 it's exhausting.

25:05

And the only thing that can make it all shut up is alcohol.

25:11

It's mid 2007 and Jessica Simpson and John Mayer are in a recording studio in Manhattan.

25:16

And for the first time in months, Jessica is getting ready to sing.

25:21

She's here to record a new version of a song from a public affair called walking round in circles.

25:27

The lyrics are all about that.

25:30

Nonstop, chorus of fear and insecurity that keeps going around and around in her head, except in the case of life, imitating art, those fears and insecurity.

25:41

Won't let her sing about her fears and insecurities she's freaking out.

25:46

So she goes to get a glass of water in the studio, kitchenette and discover something better.

25:52

Pinot Grigio.

25:53

She pours herself, a glass.

25:55

John tells her you don't need a drink, just be yourself.

26:01

Okay? Which selfish she's supposed to be. John, the person she is or the amazing person you keep telling her she could be.

26:07

Yeah, that's exactly what Jessica is thinking.

26:10

She has no idea who she even really is anymore.

26:13

And right now Jessica is full of dread.

26:16

She's not just afraid of singing.

26:19

She also doesn't want people to think.

26:21

She's just using John to help her career.

26:23

After Nick, she vowed to keep her love life and her work life separate, but John's been pressuring her to make music together.

26:32

It bothers him.

26:33

That music is a side of her. He can't have, Jessica is just too nervous to sing in front of him.

26:39

There's no music happening today.

26:41

What is happening today is the peanut Breo.

26:45

When the engineer hits record, she realizes that even though she wrote this song years ago, pre John Mayer, it's more true than ever.

26:55

She's realizing that in these past few years, she hasn't gotten stronger at all.

27:01

Forget yelling. She can't even sing.

27:04

She runs out of the studio and down a Manhattan, sidewalks sobbing.

27:09

She never records the song.

27:11

And John breaks up with her soon after.

27:14

Okay, let me just update my records.

27:16

We are now tied at four on against Again.

27:20

Thank you so much for that, Brooke.

27:22

You're welcome. I hate to say it, but we haven't seen the last of John Mayer just yet, but this particular breakup does make Jessica realized one very big thing.

27:32

She has got to get herself singing again, and she knows just where to go to find her voice.

27:40

It's 7:00 AM. One morning of that same winter in 2007, Jessica Simpson is standing outside a stucco walled compound in Nashville, Tennessee, Casey, her assistant turned a and R rep rings.

27:55

The buzzer Jessica's hands are trembling too much to do it herself.

28:00

Today is a big fucking deal for her. It's a chance to stop carrying the weight of that Kennedy center disaster around with her and to make amends with herself, with our music and with her idol, Dolly Parton, this unassuming building they're standing in front of is Dolly's office and rehearsal studio.

28:18

And Jessica is shaking like a leaf.

28:21

The gate opens and Jessica and Casey are assured inside Dolly Parton's Workday starts at 4:00 AM.

28:30

Of course it does. Yeah.

28:32

This 7:00 AM meeting is like mid day for her.

28:35

She greets Jessica with a warm envelope, Dolly hug and leads her to her chapel.

28:42

Valley's compound has a little chapel in it. Of course it does Dolly lights, a candle, and the women pray together.

28:48

And Jessica finally stopped shaking.

28:51

She starting to feel calm for the first time in a long time, like she's been on a pilgrimage and Dolly shop is the promised land.

29:00

That makes things a lot easier when they all sit down and Jessica has to tell Dolly why she's here.

29:06

She's finally ready to sing again, but she's not going back to pop this time.

29:12

She's going to sing something much closer to her heart country, Western.

29:17

That's why Jessica's made this pilgrimage.

29:20

And for the first time in her career, she can actually do exactly what she wants.

29:25

She doesn't have to sell records anymore.

29:28

A massive success of the Jessica Simpson collection has given her what folks in the business like the call, fuck you money, which is just a more fun way of saying creative freedom.

29:41

Jessica finishes her pitch by saying, I know I'm a pop star coming into the country world, but it would really be an honor to write something with you.

29:49

Wow. That's a big ask. That's like telling Oprah.

29:52

You want to give out some cars with her. It's

29:55

definitely a big ask, but Jessica also definitely deserves it, which is why Dolly doesn't miss a beat.

30:02

She says I'd love to, but I'd like to send you some songs too.

30:07

Dolly starts playing Jessica demos of tracks that she wrote, but never recorded.

30:12

Jessica can't believe her good fortune.

30:15

Part of her wants to pinch herself to make sure she isn't dreaming because this is definitely a dream, right?

30:22

She's like, am I getting punked?

30:24

Where's Ashton. And as Von Dutch trucker Hat

30:26

that trucker hat, but Dolly's generosity is totally for real.

30:31

Jessica leaves the compound with an armful of Dolly's demos and a final blessing from the queen of country herself.

30:38

I'm glad you're doing this.

30:40

Dolly says after giving her a big hug, you're just so sweet and precious.

30:44

2008 turns out to be a magical time for Jessica.

30:49

At least artistically.

30:51

She digs deep during the writing process, confronting her fears and trying to process the traumas she's experienced in our life.

30:59

But after a day long writing sessions with Nashville's top writers, she comes back to her rental house and bruises it up to numb herself.

31:07

It gets so bad that Casey starts marking the liquor bottles to keep track of the drinking.

31:13

But once the writing's done and it's time to record, she kills It.

31:19

I say, hopefully She

31:22

does. She crushes it. It's the most free she's ever felt in a recording studio.

31:27

And Dolly Parton loves Jessica's version of her song.

31:30

Do you know so much that she offers to sing on it with her?

31:35

So Jessica's dream of singing.

31:37

A duet with Dolly finally comes true to Jessica.

31:41

So honored. She named the album after that duet, do you know debuts in September of 2008 and shoots to number one on the billboard country chart, her creative gamble, eight off and now after surviving some of the lowest lows of her entire life, she's ready to show the world.

32:00

The new Jessica Simpson.

32:01

It's January of 2009, and Jessica is getting ready to perform at a chili.

32:10

Cook-off in Pembroke Pines, Florida, and she's pumped shore.

32:16

It's not Madison square garden, but Jessica doesn't need the garden anymore.

32:20

Her fashion line is practically printing money.

32:24

So artistically speaking, she can do whatever she wants.

32:27

And that means singing real songs to real people.

32:31

She's been touring as an opening act for rascal flats and having more fun on stage than she's ever had before.

32:38

In fact, the night before the cook-off she wrote in her journal, I feel like I'm right where I'm supposed to be.

32:44

Of course it helps that there's love in her life.

32:47

Again, she's embarked on a new romance with Dallas Cowboys, football star, Tony Romo.

32:52

Who's just a nice normal guy.

32:55

It's a refreshing change after John.

32:57

No, we no longer say his name in this house.

33:00

Fair enough. Jessica takes the stage in this black body suit.

33:05

High-waisted blue jeans and Fendi belt, the show bows.

33:10

Great. She isn't feeling any of that anxiety or insecurity or negativity near the end of our set.

33:17

She even opens up to the crowd about her relationship with Tony gushing.

33:21

I'm so happy because she is she's really, truly happy until photographs of her at the cook-off hit the internet a few hours after the show, they spread like wildfire and all of the headlines are screaming the same word fat for weeks after the show, Jessica can't pick up a magazine or turn on the TV without having to hear about her weight and her body.

33:49

Jessica Simpson's

33:51

gone country hots Or

33:53

not get into the gym, do something that you've put on.

33:57

Take a look at Shots taken just last summer.

33:59

Now it looks like just as enjoying a whole lot of stuff.

34:03

Cookie, all of these people are raging about a 120 pound Jessica Simpson and a pair of size four jeans.

34:11

Not that it matters because her body is her business only.

34:15

Yeah, it doesn't matter like this pisses me off so much.

34:18

Yes, same at least Elizabeth Hassleback on the view has her back.

34:23

It's horrific. You know, especially now I think women put so much pressure on themselves and they attack someone.

34:27

Who's a nice, be gorgeous just the way she is and call her fat.

34:32

It just makes me sad though. But

34:34

a few isolated defenders aren't enough to save Jessica from the avalanche of humiliation.

34:39

Her anxiety kicks into high gear and about of body dysmorphia sets in.

34:45

She feels like she can't trust what she sees in the mirror.

34:49

All that self competence, she fought so hard to get back to after what's his face.

34:54

It's all gone.

35:01

The holidays are all about families coming together from decorating Christmas trees to lighting the menorah, jingle bells, mistletoe and new year's resolutions, such a wonderful time of year.

35:12

For most families, the McCrary family preferred a different kind of family time.

35:17

They spent their time together committing brutal murders, robberies and terrorizing young people.

35:22

Working night shifts at donut shops across America, families who kills first season.

35:27

The doughnut shop murders tells a harrowing story of a family of killers led by a psychotic patriarch who made it their family business to create mayhem wherever they went, families who kill the donut shop murders premieres Tuesday, January 4th, wherever you listen to podcasts, you can binge the entire season early in ad-free when you subscribed to Wondery plus an apple podcast or the Wondery app.

35:59

It's the spring of 2009. And Jessica Simpson is in the security line at an airport in Dallas.

36:05

She's on her way to do publicity for the Jessica Simpson collection.

36:09

And because she has the best luck when she walks through the scanner, the thing lights up like a Christmas tree, a very stern looking TSA, official waves, her metal detector over Jessica's body.

36:22

And something keeps setting the damping off, which means Jessica's due for a TSA pat down.

36:30

Once the agent is convinced that Jessica doesn't have a bomb in her pocket, she softens leaning in.

36:36

She says to her, you're really not that big.

36:39

Wow. What a shitty compliment.

36:41

Right? But Jessica is just like, thank you.

36:44

And then she kicks herself because she knows that wasn't a compliment at all.

36:49

It's actually kind of a shitty thing to say full-stop.

36:52

So Jessica turns back to the woman and says, I'd be fine if I was that big though, with a little twinkle in her eye, which is way more diplomatic and sweep and what I would have said, but given everything Jessica's going through, it's not entirely true because the world really does think she's that big.

37:12

And Jessica Simpson is not fine when she gets to her hotel room in Scottsdale, Arizona, Jessica flicks on the TV left her pop career.

37:24

It's been months since that chili cook-off performance, but the talking heads on some inane entertainment, news show are still talking about her body.

37:33

The media refuses to move on.

37:35

Fashion columnists are writing tips on how not to look like her.

37:39

The New York post has started calling her jumbo, Jessica and page six, even ran a cartoon of her dumping.

37:47

Tony Romo to be with her real true love.

37:50

Ronald McDonald.

37:52

Wow. The two thousands were truly a nightmare.

37:55

Just absolute trash.

37:57

Jessica knows she can't do anything about the media picking her apart.

38:01

What really bothers her is how much she's internalized at all.

38:04

The whole thing has brought up all of her old insecurities, but there's one thing Jessica does during this time, that shows true inner strength.

38:12

She refuses to come out and offer some excuse.

38:16

Like it was just the fit of the jeans.

38:18

I'm actually a size four, even though that's totally true.

38:22

That's a form of inner strength.

38:24

I will never know you wouldn't be both.

38:26

She doesn't want to jump on the body.

38:29

Shaming bandwagon and throw fat women under the bus.

38:32

Those women are her customers.

38:34

I mean, she created a whole fashion line to make them feel seen and beautiful.

38:38

She doesn't want to become part of the problem.

38:41

So she just absorbs all that body, shaming herself back in our hotel suite, she clicks off the TV, tosses the remote across the bed and says a silent prayer.

38:52

God helped me out here.

38:54

This endless humiliation is killing my spirit.

38:57

If there's something I meant to take from this, then great.

39:00

Just help me figure out what it is.

39:02

An hour later, Jessica is at the meet and greet for her collection at a suburban department store.

39:11

There are no paparazzi here, no tabloid journalists, just regular women waiting in line to meet her everyday.

39:19

People who have nothing but love for Jessica and the clothes she makes.

39:22

It's such a relief.

39:24

It sues her to know that she's been able to make real women happy, just like she wanted near the end of the event, a woman who's been waiting over an hour, hands her a shoe dog, autograph, Jessica signs, the heel.

39:38

And as she hands the shoe back, the woman blurts out in a torrent of rehearsed words.

39:43

I just have to tell you, you really saved one of my students.

39:46

Jessica takes the woman's hand across the table and says it's okay, take your time.

39:52

Tell me your story. So the woman says I'm a school teacher, eighth grade, and this student of mine was really getting bullied about her weight.

40:02

She was just so sad.

40:03

The woman's eyes filled with tears, but she continues.

40:07

She said that she feels something akin to you.

40:11

She said that because of you, she knows she can get through it.

40:14

Oh boy, pass the Kleenex.

40:16

Please make that too.

40:18

Because by this point, Jessica is a crying mess as well.

40:22

She comes out from around the table and says, if I give you a hug, will you pass it onto her?

40:28

For me as the two women embrace, Jessica realizes that God just answered her prayer.

40:34

This is what he wants her to take from the months of public humiliation.

40:38

She went through that.

40:41

So she can stand up to the bullies for herself for that eighth grade girl and girls and women everywhere.

40:48

But before she can do that, she's going to have to solve a few problems, a little closer to home.

40:55

It's July of 2009.

40:58

And Jessica is at her parents' house in the Hollywood Hills.

41:02

She's planning to have a big birthday blow out in a week and she's there to go over the details with Tina.

41:08

The women are already deep into the party plans, enjoying the warmth, the fire pit on the patio and who should walk in to spoil the moment.

41:17

Our old friend, John fricking mayor.

41:21

Great. Now he has the address. John saw Jessica in a vanity fair profile a few months earlier and decided all of a sudden he was into her again.

41:31

So douche nozzle decided the best way to get back into her life was through her parents.

41:37

He ran the full charm offensive on Joe and Tina.

41:40

So while Jessica is setting up house in Dallas with Tony Romo or parents are having gated community playdates with her trash acts.

41:49

I mean, isn't Tina. The one who told her that John was toxic in the first place.

41:51

Just, I mean, you think she'd hate him just as much as we do, but no, John charms, the whole clan, even the house staff is crushing on him.

42:00

Hard when Jessica complaints to Tina about it, she's like he comes over and sings us love songs by the fire pit.

42:07

What's not to love Him.

42:10

Just him. Yeah. And unsolicited serenades are not the greatest thing in the world.

42:15

True. Jessica doesn't appreciate them.

42:18

Letting John Mayer crash her weekend at home.

42:21

Not that John notices or cares really that Jessica is pissed.

42:25

He stands in front of her and declares his undying love.

42:29

And then to pour it on extra thick, he says to everyone on the patio, you can all trust me to be a good man.

42:36

And then Jessica pushes him into the fire pit.

42:38

God, I wish, but she's too polite for homicide.

42:41

She's also grown a lot since she was last with John.

42:45

I mean, she's been through hell survived and come out stronger and smarter.

42:49

So, and I am paraphrasing here.

42:52

She tells John to fuck off.

42:56

Finally, Joe, she feels like she can finally see him for who he is an emotionally abusive, desperate and unstable guy.

43:05

And she doesn't want to be any of those things or want people like that in her life anymore.

43:10

Jessica's got her eyes open now in ways she never has before she loves her boyfriend, Tony and thinks he's getting ready to propose to her, but she doesn't know if she should say yes.

43:21

Tony wants her to settle down and be a Dallas Cowboys wife.

43:25

But Jessica still has big career dreams.

43:28

And now she's especially fired up to use her voice to be an example for other women, not to mention Tony's very jealous.

43:36

He won't let her do movies where she kisses her male co-star.

43:40

He checks her emails and texts to make sure she's not in touch with John Mayer.

43:46

And when he finds out that she actually saw John, while she doesn't have to worry about him proposing anymore.

43:52

Tony breaks up with her on the spot.

43:56

Wow. Jessica was devastated and pissed at herself that she didn't tell Tony about their meeting sooner.

44:02

She even cancels her big birthday party.

44:05

I mean, I'm surprised he didn't know didn't have a tracking device in her Neck.

44:08

I know. Talk about a huge red flag, but here's the thing.

44:12

This isn't the same old Jessica anymore.

44:14

Even though her knee jerk reaction is to blame herself.

44:18

When Tony circles back all like, I'm sorry.

44:21

I know you didn't cheat on me.

44:23

Let's pick up where we left off. She's like we can't because you broke up with me and by the way you did what I should have done a long time ago.

44:32

Oh shit.

44:34

Yeah. Jessica is done fucking around.

44:36

She's done playing games because by now she knows she doesn't have a man problem or a family problem or a body image problem or a career problem.

44:46

And she sure as hell doesn't have a money problem either.

44:49

Our real problem is with herself and to confront that she's going to have to dig deeper than she's ever dug before, because the only person who can fix Jessica Simpson is Jessica Simpson.

45:09

If you like our show, please give us a five-star rating and a review and be sure to tell your friends.

45:15

You can listen to even the rich ad free by joining Wondery plus in the Wondery app, you can follow the show on apple podcasts, Amazon music, and the wondering app or wherever you're listening right now.

45:27

In the episode notes, you'll find some links and offers from our sponsors.

45:30

Please support them. Another way you can support the show is by filling out a survey at wondery.com/survey.

45:36

This

45:36

is

45:36

episode

45:36

three

45:36

of

45:36

our

45:36

four-part

45:36

series,

45:36

Jessica

45:36

Simpson

45:36

blonde

45:36

billionaire

45:54

boss. We use many sources when researching our stories, but we especially recommend open book by Jessica Simpson.

46:01

I'm Orisha, Skidmore Williams, and I'm

46:03

Brooke Sifron. Dennis Hensley wrote this episode.

46:06

Kate young is our associate producer.

46:08

Our senior producers are Natalie shisha and Ben gray.

46:11

Our audio engineer is Sergio Enriquez sound design by James Morgan.

46:16

Our executive producers are Stephanie Jens, Jenny Lauer, Beckman and Marshall Louie for Wondery.

46:21

A quick heads up this episode contains some strong language adult situations and some seriously douchey behavior by a certain male singer quick heads up. This episode contains some strong language, adult situations, and some seriously douchey behavior by a certain male singer. name rhymes with Schmann Schmayer. Listener discretion is advised. It's the summer of the summer of two thousand six. Jessica and her mother Tina are in a Haverness Fashion Showroom in New York City. They're watching a parade of models saunter around the room. And the moment is a dream come true for both of them. That's because all of the models are wearing shoes created for Jessica's new fashion line. Shes Jessica Simpson Beckman, and this collection is for real everyday women. The shoes are affordable. They're comfortable. And they're made for walking. Literally. One of her first products is a pair of bright red leather boots, just like the one she wore in the video for her hit single. And they sold out immediately. What started as some sketches on a restaurant napkin over lunch with her mom shes become real. And it turns out, Tina Simpson is the perfect partner for this venture. The woman just knows how to get shit done. There's something about working in fashion that just makes Jessica happy. It all comes easily to her. She's not stressing about being perfect or thin or a good wife. This warehouse full of discount shoes is Jessica Simpson's happy place. But unfortunately, the world outside that warehouse is still a complicated hot mess. And so is Jessica's new boyfriend? He's obsessed with her. He's the smartest person she's ever met before, and the sex is amazing. Jessica's usual motto is true love weights. But with this guy, she's all about the try before you buy. And those two are constantly trying. And when they aren't, they're texting. A new love how New love. How perfect. It should be. Except that every time Jessica texts Lewy make smarty pants, she has her assistant proofread it before she hit send. Shes critical of everything she says and does. But he always says it's because he wants her to be her best self. Jessica feels like he's so much smarter than her. He makes her feel dumb. Oh, insert red flag Insert red flag emoji. That's what her mom has been trying to tell her. But now Tina just rolls her eyes and says, that is a terrible relationship if you have to be scared that you misspelled something. Cate. Can we call this episode Tina Simpson as spitting straight facts? Oh, just wait a few minutes. When Tina's wrong, she's wrong hard. But we've got to give credit words too. Because at this exact moment, she's right on the money about this new guy. Dude is toxic. And Jessica's going to go through hell before she figures that out. Alright, friends. Let's talk dating specifically dating on match. American singles have spoken being hot is out and being emotionally mature is in. You heard it here first, guys. I mean, it's pretty interesting. Listen to this. Match's annual survey found that for the first time in more than a decade, emotional maturity ranks higher than attractive on priority lists. So emotionally mature adults are the new sexy. I mean, your time to shine. Take it from me. Yeah. There's nothing hotter than dating someone that thinks running errands together counts as a date. So I don't know, Rajeev, are you ready for something more? Now is a great time to download match because right now messaging your top matches is free. If you know what you want and you're not afraid to say it, download match today. Venmo is a weekly, sometimes daily, part of my life. From rent and utilities to concert tickets and dinners out, Venmo makes it so easy to share the fun and split the check-in the app. And next time you split the bill, you can score $10 when you pay with And next time you split the bill, you can score ten dollars when you pay with Venmo. You heard me ordering delivery for the group. Get paid back before your meal arrives, share a ride with your roommate, split the car and the Get paid back before your meal arrives. Share ride with your roommate, split the Cate, and the charge. And if you sign up today with code Wondery, you'll get $10 to send an spend offer ends December 31st, 2021 limited availability see terms at And if you sign up today with Cate Wandry, you'll get ten dollars to send and spend. Offers ends December thirty first twenty twenty one limited availability. C terms at Venmo dot me slash sign up ten. venmo.me/signup. 10 that's, $10 with promo code Wondery ten dollars with promo code wondery. From Wondery. I am Arisha Skidmore Williams and I'm Brooks I'm Chicha Skidmore Williams, and I'm Brook Siffron. And this is even the rich. In our last episode, Nick and Jessica's reality shes newlyweds Cate Jessica a huge star, and left Nick in the dust. The fallout wreck their relationship and ended their marriage. Now, Jessica's Honor owned for a first time in her life. She's partying a lot and dating her way through Hollywood. But behind the good time girl paparazzi shes, Jessica woman under a lot of pressure. She really needs money. After all, she's still the family business. Jessica promised her dad she'd make back all the money she gave Nick in their divorce. Now shes has to figure out how. This is episode 3. Walking in circles. It's the summer of two thousand six. And Jessica Simpson is making her way through the loud clinging kitchen of a trendy SoHo hotel. hotel. A bunch of smells hit her nostrils all at bunch of smells hit her nostrils all at once as she walks. Restaurant trash, coffee grounds, and french fries. She's on a top secret mission, so she's keeping her head down. She's in incognito mode, all black clothing, and massive sunglasses. But of course, there's high heels. There's always high heels. Jessica's motto, is the higher the heel, the closer to god. Okay. Mine is the higher the heel, the weaker the ankles, but for her. Jessica, steps into the creaky service elevator and rides to the penthouse. Her excitement level rising with each floor. When the elevator stops, shes door slides open, and she peaks out. All clear. She gives her hair a sex the shampoo commercial shakeout that walks to the Penhouse store and knocks softly three times. A second later, he opens the door. John Mayer. His dark hair is shaggy and unkempt, just the way Jessica likes it. And he's got a look on his face like he's starving and she's a prime rib. Shes tumbles into his arms and right into his bed. Shes sex is hot and full of passion. And when John's not touching her, he's talking about her. He's telling her what he loves about her body or about writing songs about it. them. Yeah, just like Yeah. Just like that. Although that song actually predates Jessica, but the sentiment definitely applies. And Jessica loves how assessed he is with her. He makes her feel seductive and powerful. When she gets out of bed to go to the bathroom, he winds Theres are you going? It's a refreshing change from her ex Nicolas Shes. By the end of their marriage, he barely cared what time zone she was in. All right, hold on, back Hold on Beckman How did Jessica even meet this stage five clanger? Good phrasing. So They met at a Grammy party back when she was still married. John started sending her these friendly emails, and as soon as Jessica was single, he pounced. And then he kept pouncing. They've had a lot of secret rendezvous like this on both coasts. And when work keeps them apart, John watches Jessica's proactive infomercials late at night to feel closer to her. I guess there's nothing hotter than acne I guess there's nothing harder than acne Or watching infomercials on watching infomercials on repeat. Yeah. Back in the SoHo hotel room though, the TV is definitely off. Jessica and John are still up. When the light of the sun starts to stream through the up when the light of the sun starts to stream through the blinds. If there's one thing these guys do more than have sex, it's talk. Only the talking part isn't quite as good as this x because it's mostly just John talking. John Mayers in Olympic level chatterbox. He loves to ask provocative questions and challenge Jessica's convictions. He loves to say totally supportive, not at all passive aggressive things to her like, I think your true self is so much greater than the person you're settling on being. Says the guy who's jacking off to acne commercials, I mean, everyone should get a facial from time to time. True. But you have to remember. This is the first time in her life that Jessica's been on her own. Shes trying to figure out who she is outside of the televised car wreck that was her marriage. So when John tells her, I believe there's a truly great woman inside you just waiting to come out. Jessica agrees. Now, she just has to go out and find her. It's Jenz two thousand six, and Jessica Simpson looks like sacks on wheels, literally. She's in roller skates and dressed in skimpy red shorts and a matching tube cup. Her feathered therafosset hair gorgeously frames her perfectly made up face. A harness is wrapped around her waist and attached to a rolling camera cart. together. She and the cart sail around a San Fernando valley roller rink, all the disco era strains of her new single a public affair Philby air she's filming a music video for her upcoming fifth studio she and the cart sail around a San Fernando Valley roller ring. While the disco era strains of her new single, a public air, fill the air. She's filming a music video for her upcoming fifth studio album. The roller disco concept was her mom's idea. Even though her dad is Jessica's official manager, Tina is the one with the most inspired shes, and this video concept is no exception. As Jessica rolls around the ring with her famous girlfriends, Christina Applegate, Christina Million, and Eva Longoria. She looks like a shining disco doll who doesn't have a Cate in the world. Her ex husband, Nicholas Shea's post divorce album, was a little rough for her. It was called what's left of me and featured tracks like, I can't hate you anymore, that were clearly about their doomed marriage. But Jessica doesn't feel the need to put anyone down. Not one song on the album is about Nick. Nick. She just wants to move She just wants to move on. I found love really young. You know, people change. We all change. And it's okay. It's changed. That's Jessica talking to a small studio crowd during an MTV special promoting the album. She's sitting on the edge of the stage answering from an all female crowd, and she's definitely channeling those late night conversations with Johnny Knoxville. She was terrified of change until he told her to embrace it. The problem is, Johnny was wrong about one thing. Change is fucking hard because underneath that confident I got this surface, Jessica is barely holding it together. When you're going through difficult times, how do you get through it? I sing. So this song, actually, I was going through a really hard time, a very hard time. This was Christmas and I got it. I understood I understood it. And then she sings the Patty Griffin song, let him fly and totally breaks down crying. So while the album keeps shouting, I'm Cate. Everything's awesome. Let's dance. Deep down, Jessica is scared. A public affair is the first album she's executive producing all on her own. No more Tommy Matola telling her what to sing, what to wear, or how much she has to weigh. She co wrote ten of the thirteen songs, and this is all her vision. Exciting but terrifying. And it gets even more terrifying when the world responds to the album with a resounding. Shes record theres fine, but Jessica wasn't going for fine. She needed this to be a hit. But it turns out the world just isn't that interested in a happy Jessica Simpson. Not after she broke up up. America's favorite couple Johnny favorite couple. Johnny Knoxville Knoxville. And Steve-O good Steve O. Good point. America's second favorite couple. Besides her work on her fashion line, Shes only got one person to help soften the blows. Captain supportive John Mayer, but this love fest will end. A lot, like, on a monthly basis because there's one other problem with John Mayer. He keeps breaking up with her. It's December of two thousand six, and Jessica is pacing around a dressing room at the Kennedy Center Opera House in Washington DC. She's there to sing nine to five at a Dolly Parton tribute that's going to be televised on CBS. Jessica's honored to be there and she really wants to do well. And not just because her singing career of late has an exact Beeb and Steller. She wants to rock this performance because she's going to be singing for dolly. Dolly parton is Jessica's ultimate role model. She's another curvy blonde from the south who everyone underestimated, and now she basically rules the school. Shes is full of other a listers, like Reba McIntyre, Reese Switherspoon, and Shes Twain. Jessica really should be hanging in the green room with them. But she's not feeling like an a lister tonight. In fact, she's not leaving the dressing room until she has to because that's where the whiskey is. Shes night before John Mayer broke up with her again over email. My god. The night before she's performing at that Kennedy Center, Dick move, Yeah. He has a knack for timing these breakups for maximum catastrophic effect, and effect. And he likes to make them even more dramatic and confusing by attaching likes to make them even more dramatic and confusing by attaching m p threes. This time, he sends the aerosmith song angel. I'd be like, Lewy Mel who dis. Exactly. But it said Jessica into this total tailspin. So instead of rehearsing nine to five, Jessica Cate up all night going over the lyrics of Angel trying to figure out what John is trying to tell her. Is there an answer to what she did wrong? Is it because she's not smart enough for him? Now Jessica's exhausted because she hasn't slept and she feels like she's having a nervous break down because she can't get Steven Tyler out of her head, which brings us back to the whiskey. She thinks the booze and a lot of it is the only thing that's going to get her through the night. Tina and Joe think otherwise, they keep telling her, you need to not be drinking. But Jessica's like, this doesn't make me drunk at all. And also, why are there six of you guys? So Jessica's totally fine and not at all drunk when the phone rings in her dressing room a few minutes before she goes on. And of course, It's John Mayer. The second, it becomes clear he's not calling to apologize and diffuse the situation. They start going at it. Jessica screams at him. How could you do this to me? Why do I have to be thinking of you all the time? If you're going to let me go, let me go. John hates dealing with her when she's drunk, so he just hangs up on her. And that's when the reality of her condition hits Jessica. She really is totally and completely drunk. And Reese Witherspoon really is introducing her to a pack house. Jessica's never gone on stage drunk before, and yet here she is walking out onto the stage of Kennedy Center. She hears her band start playing nine to five, then she hears herself singing along, and here's the thing. Maybe she could have pulled off a slower power ballad like angel that night. But nine to five is all dolly. That songs got places to be. And Jessica can't keep up with it. She gets to the lyrics. They let you dream just to watch them shatter, and she shatters. Shes freezes. Oh, no. Not again. Again. Except it's not pre pubescent Justin Timberlake and the Mascadir's watch this time. Jessica looks up at the balcony and sees president Barack Obama and first lady Michelle. Right next to all of these other dignitaries in black tie. Theres she locks eyes with dolly herself, who's looking down at her with grave concern. Seeing her idle right there before her very eyes shakes Jessica out of her liquor induced stupor. She's failing. Shes not good enough for dolly. So theres, right in the middle of the performance, Jessica says, I'm so sorry. It's an honor to be here, but the song is too good for me. Then she walks off stage with a drunken awkward hop. After the show, dolly shows up in her dressing room. She's not angry. In fact, she gives her a pep talk. Shes slips Jessica her card with a handwritten phone number on the back and tells her, if you ever need anything, You call me. Ugh, we don't deserve dolly. We really We really don't. And in the meantime, dolly's like, the band's waiting for you. Get back out there and do the song and we'll cut it into the show when it theres. But when Jessica heads back to the stage and looks out into the ornate, empty opera house, she can't do it. Not because she's too drunk, but because she's too sad. Shes feels totally and completely empty. It takes all her strength to turn to the band and tell them, I'm sorry for wasting your time. Then she walks into the wings Joe is waiting and tells him, I will never sing again. It's a decision that will shape the rest of her life. So if you've listened to our show for a while, you might have heard us talk about best fiends, one of the best match, three mobile puzzle games out you've listened to our show for a while, you might have heard us talk about best fiends, one of the best match three mobile puzzle games out there. Could I tell you how glad I've been to have best fiends on my phone throughout all of the holiday madness this year? It's the perfect pick me up when I need a break from the chaos. Which is often. Oh, god. I hear that. Yes. So I'm a really big fan of the gameplay. It's pretty It's pretty unique. It's got a really fun It's got a really fun storyline. It's got collectible fiends that are absolutely It's got collectible fiends that are absolutely adorable. And it's got a ton of fun puzzles, which I, of course And it's got ton of fun puzzles, which I of course love. They've got literally thousands of levels with more added all the They've got literally thousands of levels with more added all the time. So there's always a fresh challenge waiting for So there's always a fresh challenge waiting for you. And you just need that mental pick me you you just need that mental pick me up. Yeah. Yeah. And also traveling and no wifi, no And also, traveling and no WiFi, no problem. You can play best fiends You can play best fiends wherever and whenever you want with offline mode. Comes in handy for all that flying. So even if your holiday travels have taken you off the beaten bath, you can still So even if your holiday travels have taken you off the beaten path, you can still play. Yeah. Like I, this is one thing when I'm flying these games are my go-to because it's just, I don't Like, I This is one thing when I'm flying these games are my go to. Yeah. Because it's just don't know. know. It's It's fun. It's It's relaxing. It keeps my mind busy. So best ones is perfect for airplane So best one is perfect. For Emily travel. Take it from Take it for me. I love a good distraction. Yeah. You guys can download Fiends free today on the App Store or Google Play. That's friends without the r, best fiends. Hi. I'm Kelly Martin. To launch a life of creativity, creativity. You just need a little spark and a big just need a little spark and a big break. I'm Chad On our new podcast series, The Big Brake. Kelly and I talk with actors and take a deep dive into the magical moments that changed their careers and lives forever. In each episode, we'll take our guests back to the very beginning before a starring role, Golden Globe nominations, the Tony Wins, and the adoring fans. We'll talk about the stumbles and obstacles they faced along the way who influenced them and where they find their inspiration now. The big break goes deeper than typical celebrity interviews. Chad and I have been working actors for almost our higher lives will reveal the hard work and lucky breaks it takes to become a successful leading actor. Because for every DiCaprio or Jolie, There are thousands who grind it out every day, making their dreams of a creative life come true. Join us on the big break, where we explore what it takes to make it Follow the big break on Apple Podcasts, Spotify, Amazon Music, or wherever you're listening now. It's early two thousand seven. And Jessica Simpson is hanging out backstage at a concert hall in Adelaide Australia. Australia. She isn't there to isn't theres to perform. She's still reeling from the Kennedy Center debacle, and she meant it when she told her dad she'd never sing again. She's also dyed her signature blonde hair this dark shade of brown. It's her attempt to be anybody other than the drunk mess who closed out two thousand six by disappointing Dolly Parton, a president, her fans, and herself. Dying her hair is the easy fun change she needs right now, but it doesn't magically make our problems disappear. Or get her shitty on again, off again boyfriend to treat her better. In fact, Jessica's here at this concert hall to support her boyfriend. John Mayer. Oh my god. What are we up to now? Like, four on Jenz at this point? Something like that. But right now, Jessica is craving comfort. Social pick what she can get. Because deep down, part of her thinks John is all she deserves. But another part of her thinks that she'll never be good enough for him. It's all very complicated and a little sad. Suffice it to say, Jessica is fine playing groupie on the John Mayor tour bus. When a girl working backstage at the venue asks her, what are we going to hear you sing again? Jessica lies and says, oh, soon. The truth is, even if she hadn't recently vowed to stop singing, She'd be scared to make music around John. When she looks at him, she sees a guitar god and a Grammy darling. Which just makes her feel even worse. Overall, she's not in a good place. It doesn't even register for her that back in the Cate shes Simpson collection is blowing up. She's racking up millions of dollars in sales at department stores like Macy's and Dillard's, Did you say Macy's? Just kidding. No. That's a really big win for her. Yeah. Through all of this John drama and misery, shes still scanning the crowd at every concert for inspiration. She photographs random people on the street, street. She snaps hundreds of photos to send back to Tina and the design snaps hundreds of photos to send back Tina and the design team. She wants to capture how women in the real world How they like their jeans to fit and where they're cropping their crop tops. Jessica even creates lookbooks on the tour bus. She and John fall in love with shes high end designer in Japan. So Jessica tries to imagine how the spirit of those luxury pieces could be in corporated into items a regular girl could easily afford. Thinking about her collection customers is definitely a bright spot in her life right now. But it's also bittersweet because she's still that girl who just wanted to fit in and be like everybody else. And everything else she's dealing with at the moment he'll so far away from that. Because there is nothing ordinary or regular or understated about John. On the tour, he really starts to pour it on thick with the grand gestures. He buys her a diamond necklace at Tiffany's. He arranges a private tour for them of the austine chapel in Rome. But the splashier and fancier he gets, the more uncomfortable and less like herself she feels. Theres she worries. She's just going to disappoint John and on and on and on. This roller coaster is making me nauseous. Yeah. You and me both. Jessica's worst fears play out in a loop in her head twenty four seven. It's exhausting. And the only thing that can make it all shut up is alcohol. It's made two thousand seven, and Jessica Simpson and John Mayer are in a recording studio in Manhattan. And for the first time in months, Jessica is getting ready to sing. She's here to record a new version of a song from a public affair. Called walking around in circles. The lyrics are all about that nonstop chorus of fear and insecurity, that keeps going around and around in her head. Except in a case of life imitating art, those fears and insecurity. Won't let her sing about her fears and insecurities she's freaking won't let her sing about her fears and insecurities. She's freaking out. So she goes to get glass of water in the studio kitchenette and discover something better. Pino Grigio. She pours herself a glass. John tells her, you don't need a drink. Just be yourself. Cate. Which self is she supposed to be, John, the person she is, or the amazing person you keep telling her she could be? Yeah. That's exactly what Jessica's thinking. She has no idea who she even really is anymore. And right now, Jessica is full of dread. She's not just afraid of singing. She also doesn't want people to think she's just using John to help her career. After Nick, she vowed to keep her love life and her work life separate. But John's been pressuring her to make music together. It bothers him that music is a side of her he can't have. Jessica's just too nervous to sing in front him. Theres no music happening today. What is happening today is the Peanuts Show. When the engineer hits record, Shes realizes that even though she wrote this song years ago, Pre John Mayer, it's more true than ever. She's realizing that in these past few years, she hasn't gotten stronger at all. Forget yelling, yelling. She can't even she can't even sing. sing. She runs out of the studio and down a Manhattan, sidewalks runs out of the studio and down a Manhattan sidewalk sobbing. She never records the song. And John breaks up with her soon after. Okay. Let me just update my records. We are now tied at four on Jenz and four off agains. Thank you so much for that, Brooke. You're welcome. I hate to say it, but we haven't seen the last of John Mayor just yet. But this particular breakup does make Jessica realize one very big thing. She has got to get herself singing again. And she knows just where to go to find her voice. It's seven AM one morning of that same winter in two thousand seven. Jessica Simpson is standing outside a stucco walled compound in Nashville, Tennessee. Casey, her assistant turned ANR rep, rings the buzzer. Jessica's hands are trumbling too much to do it herself. Today is a big fucking deal for her. It's a chance to stop carrying the weight of that Kennedy Center disaster around with shes. Omega men's with herself, with her music, and with her idol dolly parton. This unassuming building they're standing in front of is dolly's office and rehearsal studio. And Jessica is shaking like a leaf. Shes gate opens, and Jessica and Cate are ushered inside. Dolly Parton's Workday starts at four AM. AM. Of course it Of course, it does. Yeah. This seven AM meeting is like midday for her. She her. She greets Jessica with a warm envelope, Dolly hug and leads her to her Jessica with a warm, enveloping dolly hug. And leads her to her chapel. Dolly's compound has a little chapel in it. Of course, it does. Dolly lights a candle and the women pray together. And Jessica finally stopped shaking. She's starting to feel calm for the first time in a long time. Like she's been on a pilgrimage and dolly's shop is the promised land. That makes things a lot easier when they all sit down and Jessica to tell Dolly why she's here. She's finally ready to sing again, but she's not going back to pop. This time, She's going to sing something much closer to her heart. Country Western. That's why Jessica's made this pilgrimage. And for the first time in her career, she can actually do exactly what she wants. She doesn't have to sell records anymore. massive success of the Jessica Simpson Beckman has given her what folks in the business like to call fuck you money. Which is just a more fun way of saying Cate freedom. freedom. Jessica finishes her pitch by saying, I know I'm a pop star coming into the country world, but it would really be an honor to write something with finishes her pitch by saying, I know I'm a pop star coming into the country world, but it would really be an honor to write something with you. Whoa. That's a big ask. That's Cate telling Oprah. You want to give out some cars with you wanna give out some cars with her. Yeah. It's definitely a big ask, but Jessica also definitely deserves it, which is why dolly doesn't miss a beat. She says, I'd love to, but I'd like to send you some songs too. Dolly starts playing Jessica demos of tracks that she wrote but never recorded. Jessica can't believe her good fortune. Part of her wants to pinch herself to make sure she isn't dreaming because this is definitely a dream. Right? She's like, am I getting pumped? Where's Shes and his Vanduch trucker hat? That trucker hat. But dolly's generosity is totally for real. Jessica leaves the compound with an armful of dolly's demos and a final blessing from the queen of country herself. I'm glad you're doing this. Dolly says after giving her a big hug, theres just so sweet and precious. Two thousand eight turns out to be a magical time for Jessica, at least artistically. She digs deep during the writing process confronting her fears and trying to process the traumas she's experienced in her life. But after day long writing sessions with Nashville's top writers, Shes comes back to her rental house and loses it up to numb herself. It gets so bad that Casey starts marking the liquor bottles to keep track of the drinking. But once the writing's done and it's time to record, she kills it. I say hopefully Shes She crushes it. It's the most free she's ever felt in a recording studio. And Dolly Parton loves Jessica's version of her song. Do you know? So much that she offers to sing on it with her. So Jessica's dream of singing a duet with dolly finally comes true too. Jessica's so honored shes names the album after that duet. Do you know Cate Hughes in September of two thousand eight? And she suits to number one on the Billboard Country Chart. Her creative gamble paid off. And now, after surviving some of the lowest lows of her entire life, she's ready to show the world the new Jessica Simpson. It's January of two thousand nine, and Jessica is getting ready to perform at a chili cook off in Pembroke Pines, Florida. And she's pumped. Sure. It's not Madison Square Garden, but Jessica doesn't need the garden anymore. Her fashion line is practically printing money. So artistically speaking, can do whatever she wants. And that means singing real songs to real people. She's been touring as an opening act for Rascal flats and having more fun on stage than she's ever had before. In fact, the night before the cook off, she wrote in her journal, I feel like I'm right where I'm supposed to be. Of course, it helps that there's love in her life again. She's embarked on a new romance with Dallas Cowboys football star, Tony Romo, who's just a nice normal guy. It's refreshing change after John. No. We no longer say his name in this house. We're clear enough. Jessica takes the stage in this black body Just ago takes the stage in this black bodysuit, high waisted blue jeans and fendi belt. The show goes great. She isn't feeling any of that anxiety or insecurity or negativity. Near the end of her set, she even opens to the crowd about her relationship with Tony. Fushing, I'm so happy because she is. She's really, truly happy. Until photographs of her at the cook off hit the Internet a few hours after the show. They spread like wildfire. And all of the headlines are screaming the same word. Fat. For weeks after the show, Jessica can't pick up a magazine or turn on the TV without having to hear about her weight and her body. Jessica Simpson's gone country. Hot or not. Jessica hit them to the gym. Pick on. Take a look at look at these shots taken just last summer. Now it looks like Jess enjoying a whole lot of southern cooking. All of these people are raging about a one hundred and twenty pound Jessica Simpson in pair of size four jeans. Not that it matters because her body is her business only. Yeah. It doesn't matter. Like, this pisses me off so much. Yeah. Same. Nathalie least Elizabeth Hasselback on the view has her back. It's horrific. You know, especially now think women put so much pressure on themselves and they attack someone who's, shes, Be gorgeous just the way she is and call her fat. It just makes I saw them. But a few isolated defenders aren't enough to save Jessica from the avalanche of humiliation. Her anxiety kicks into high gear and about a body dysmorpia in. Shes feels like she can't trust what she sees in the mirror. All that self confident she fought so hard to get back to after what's his face It's all gone. The holidays are all about families coming together from decorating Christmas trees to lighting the menorah, jingle bells, mistletoe and new year's resolutions, such a wonderful time of The holidays are all about families coming together. From decorating Christmas trees to lighting the menorah, jingle bells, Missletoe, and New Year's resolutions. Such a wonderful time of year for most Nathalie. Shes family preferred a different kind of family time. They spent their time together committing brutal murders, robberies, and terrorizing young people working night shifts at shops across America. Families who kills first season, the donut shop murders, tells the harrowing story of a family of killers, led by a psychotic patriarch who made it their family business to create mayhem wherever they went. Families who kill shes shop murders, premieres Tuesday your a fourth theres you listen to podcasts. You can binge the entire season early in ad free when you subscribe to wondering PlaySee Apple Podcasts or the Wonderry app. It's the spring of two thousand nine, and Jessica Simpson is in the security line at an airport in Dallas. She's on her way to do publicity for the Jessica Simpson Beckman. And because she has the best luck, when she walks through the scanner, shes thing lights up like a Christmas tree. A very stern looking TSA official waves her metal detector over Jessica's body, and something keeps setting the dampening off, which means Jessica's due for a TSA pack down. Once down. Once the agent is convinced that Jessica doesn't have a bomb in her pocket, she softens leaning the agent is vince that Jessica doesn't have a bomb in her pocket, she softens.leaning in, she says to her, you're really not that big. Wow. What a shitty What a shitty compliment. Right? But Jessica's just like, thank you, and then she kicks herself. Because she knows that wasn't a compliment at all. It's actually kind of a shitty thing to say full stop. Mhmm. So Jessica turns back to the woman and says, I'd be fine if I was that big, though, with a little twinkle in her eye, which is way more diplomatic and sweet than what I would have said. But given everything Jessica's going through, it's not entirely true because the world really does think she's that big. And Jessica Simpson is not fine. Hensley gets to her hotel room in Scottsdale, Arizona, Jessica flicks on the TV. Jessica Simpson's laptop career behind. It's been months since that chili cook off performance, but the talking heads on some inane entertainment news show are still talking about her body. The media refuses to move on. Fashion columnist are writing tips on how not to look like her. The New York Post has started calling her jumbo Jessica, And six even ran a cartoon of her dumping Tony Romo to be with her real true love, Ronald Mcdonald. Wow. Shes two thousands were truly a nightmare. Just absolute trash. Jessica knows she can't do anything about the media picking her apart. What really bothers her is how much she's internalized Cate all. The whole thing has brought up all of her old insecurities. But there's one thing Jessica does during this time that shows true inner strength. She refuses to come out and offer some excuse like It was just the fit of the jeans. I'm actually a size four even though that's totally true. That's a form of inner strength, I will never know. You wouldn't be both. She doesn't want to jump on the body shaming bandwagon and throw fat women under the bus. Those women are her customers. I mean, she created a whole fashion line to make them feel seen and beautiful. She doesn't wanna become part of problem. So she just absorbs all that body shaming herself. Beckman our hotel suite, she clicks off the TV. Tosses a remote across the bed and says a silent prayer. God help me out here. This endless humiliation is killing my spirit. If there's something I meant to take from this, then great. Just help me figure out what it is. An hour later, Jessica's at the meet and greet for her collection at a suburban department store. There are no Aperoxy here, no tabloid journalists, just regular women waiting in line to meet her. Everyday people who have nothing but love for Jessica and the clothes she makes. It's such a relief. It soothes her to know that she's been able to make real women happy just like she wanted. Near the end of the event, a woman who's been waiting over an hour hands her a shoe to autograph. Jessica signs the heel. And as she hands a shoe back, Shes woman blurts out in a torrent of rehearsed words. I just have to tell you you really saved one of my students. Jessica takes the woman's hand across the table and says, it's Cate, take your time, tell me your story. So the woman says, I'm a school teacher, eighth grade, and this student of mine was really getting bullied about her weight. She was just so sad. Shes woman's eyes fill with tears, but she continues. Shes said that she feels something akin to you. She said that because of you, Shes knows she can get through it. Oh, boy. Pass the Kleenex, PlaySee. Cate that too. Because by this point, Jessica's a crying mess as well. She comes out from around the table and says, if I give you a hug, will you pass it on to her for me? As the two women embrace, Jessica realizes that God just answered her prayer. This is what he wants her to take from the months of public humiliation. She went through that so she can stand up to the bullies for herself, for that eighth grade girl, and girls and women everywhere. But before she can do that, she's going to have to solve a few problems a little closer to home. It's July of two thousand nine, and Jessica's at her parents house in the Hollywood hills. She's planning to have a big birthday blowout in a week. And she's there to go over the details with Tina. The women are already deep into the party PlaySee, enjoying the warmth the fire pit on the patio. And who should walk in to spoil the moment? Our old friend, John freaking mayor. Great. Now he has the address. John saw Jessica in a vanity fair profile a few months earlier and decided all of a sudden he was into her again. So this douche nozzle decided the best way to get back into her life was through her parents. He ran the full harm offensive on Joe and Tina. So while Jessica is setting up house in Dallas with Tony Romo, her parents are having gated community play with her trash act I mean, isn't Tina the one who told her that John was toxic in the first place? Yes. I mean, you'd think she'd hate him just as much as we do, but no. John charms the whole clan, even the house staff is crushing on him hard. When Jessica complains to Tina about it, she's like, He comes over and sings us love songs by the fire pit. What's not to love? Him? Just him. Yeah. And unsolicited serenades are not the greatest thing in the world. True. Jessica doesn't appreciate them letting John Mayor crash her weekend at home. Not that John notices or cares really that Jessica's pissed. pissed. He stands in front of her and declares his undying He stands in front of her and declares his undying love. And then to pour it on extra thick, He says to everyone on the patio, you cannot trust me to be a good man. And then Jessica pushes him into the fire pit, god, I wish. But she's too polite for homicide. Shes also grown a lot since she was last with John. I mean, she's been through hell, survived, and come out stronger and smarter. So and I am paraphrasing here. She tells John to fuck off. Finally. Joe, she feels like she can finally see him for who he is an emotionally abusive, desperate and unstable Shes feels like she can finally see him for who he is. An emotionally abusive, deaf spirit, an unstable guy. And she doesn't want to be any of those things or want people like that in her life anymore. Jessica's got her eyes open now in ways she never has before. She loves her boyfriend, Tony, and thinks he's getting ready to propose to her. But she doesn't know if she should say yes. Tony wants her to settle down and be a Dallas cowboy's wife, but Jessica still has big career dreams. And now she's especially fired up to use her voice to be an example for other women. Not to mention, Tony's very jealous. He won't let her do movies where she kisses her male co star. He checks her emails and texts to make sure she's not in touch with John Mayer. And when he finds out that she actually saw John? Well, she doesn't have to worry about him proposing anymore. Tony breaks up with her on the spot. Wow. Jessica's devastated, and pissed set herself that she didn't tell Tony about their meeting sooner. sooner. She even cancels her big birthday She even canceled her big birthday party, I I mean, I'm surprised he didn't know didn't have a tracking device in her I'm surprised he didn't know. Didn't he have a tracking device in her neck? I know. Talk about a huge red flag. But here's the thing. This isn't the same old Jessica anymore. Even though her knee jerk reaction is to blame herself, when Tony circles back all like, I'm sorry. I know you didn't cheat on me. Let's pick up where we left off. She's like, we can't. Because you broke up with me, and by the way, You did what I should have done a long time ago. Oh, shit. Yeah. Jessica's done fucking around. She's done playing games. Because by now, she knows she doesn't have a man problem or a family problem or a body image problem or a career problem. And she sure as hell doesn't have a money problem either. A real problem is with herself. And to confront that, she's going to have to dig deeper than she's ever dug before because the only person who can fix Jessica Simpson is Jessica Simpson. If Simpson. If you like our show, please give us a five-star rating and a review and be sure to tell your like our show, please give us a five star rating and a review, and be sure to tell your friends. You can listen to even the rich ad free by joining Wonderry Plus in the Wonderry app. You can follow shes show on Apple Podcasts, Amazon Music, and Wonderry app. Or wherever you're listening right now. In the episode notes, you'll find some links and offers from our sponsors. Please support them. Another way you can support the show is by filling out a survey at wundery dot com slash survey. This is episode three of our four part series Jessica Simpson, Blonde, Millionaire boss. boss. We use many sources when researching our stories, but we especially recommend open book by Jessica use many sources when researching our stories, but we especially recommend Open Book by Jessica absent. I'm Aricia Skidmore Williams, and I'm Brook Siffron. Dennis Hensley wrote this episode. episode. Kate young is our associate Young is our associate producer. Our senior producers are now Chicha and Ben Gray. Our audio engineer is Sergio Enriquez, Sound Design by James Morgan. Our executive producers are Stephanie Jenz, Jenny Lauber Beckman and Marshall Lewy for Wonderry.