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Hello and welcome everyone to Trashy

0:27

Divorces, everyone's favorite good

0:30

podcast about bad relationships.

0:32

My name is Alicia and Stacey,

0:35

you've got the giant of late night

0:38

for us today. I do. Not

0:40

only is David Letterman a giant

0:42

of late night, he's also, it would

0:45

appear, been kind of a giant dirtbag

0:47

to the women in his life for, you know,

0:49

most of it. On the plus side,

0:52

one of his exes, who is an Emmy

0:54

award winning comedy writer herself,

0:57

gets in a few excellent zings here

0:58

and there. Love it. Before

1:01

we get into Dave's top 10 trashiest

1:03

moments then, let's take a quick look

1:05

into our magic mirror here and thank our

1:08

newest Patreon supporters over at Patreon.com

1:11

slash Trashy Divorces, enjoying

1:13

early ad-free episodes, bonus

1:15

divorces, Zoom salons, and much,

1:17

much more. Thank you so much to

1:19

Kai and KM for joining

1:22

us at Patreon. Holy cats,

1:24

simply the best. All y'all and

1:26

you for coming back for this no

1:29

tell lover kind of episode

1:31

of Trashy Divorces. Stacey,

1:33

I think it is high time that we

1:36

go, go, go.

1:49

Oh, Stacey, I'm excited about this one. I

1:51

have clearly missed the David

1:54

Letterman trashy radar scoop.

1:57

I'm excited. There were parts of the story I

1:59

had completely forgotten about as well.

2:02

Alicia David Letterman's brand of humor

2:05

and wit was different from what

2:07

many American audiences were used to when

2:09

he burst onto the scene. Millions

2:12

loved his comedic style, but you know it

2:14

wasn't for everybody. He was often

2:16

criticized for being cold and sometimes

2:18

caustic, but in any

2:20

case he entertained audiences for more

2:22

than 30 years. He continues to.

2:25

He's kept his personal life very private

2:27

for most of his career, often

2:29

coming off as something of an enigma. He has

2:32

a midwestern stoicism and

2:34

seems to be most comfortable mocking the world

2:36

and the people around him.

2:38

He's quick, he's quirky, and he's

2:40

great at improvisational conversations

2:42

with guests.

2:44

No one reaches the pinnacle of a career

2:46

like his though without a great deal of effort

2:49

and energy and the amount

2:51

of time and effort that he put

2:53

into professional success certainly caused

2:56

a lot of problems in his personal life, although

2:58

also some of his personal peccadillos

3:01

may have also contributed. He's

3:03

the longest running late night broadcaster in

3:05

American history and he's the winner of

3:07

many awards and is also a Kennedy

3:10

Center

3:10

honoree. All impressive. He

3:12

seems to have taken some time to get to know himself

3:15

and understand better how he operates

3:18

in relationships, but this did not come easily

3:20

for him. Now at the tender

3:22

age of 76 he seems to have finally

3:25

figured out kind of who he is and

3:27

what he wants to be.

3:28

Should he ever decide to grow up? Better late

3:31

than never. David Letterman was

3:33

born on April 12,

3:35

1947. So in Aries? Yes, Aries, man.

3:38

Sparky, sparky, in broad ripple

3:40

Indiana. It's

3:42

a suburb of Indianapolis. He

3:44

was the middle child of Harry and Dorothy

3:46

Letterman. There was an older sister and

3:48

a younger sister, so a lot of girls in

3:50

that household.

3:51

His parents were children of the Depression.

3:54

That of course had a great influence on their

3:56

personalities and their behaviors. Dorothy, for instance,

3:58

was

3:58

a young man. He was a young man. He was a young man.

3:59

was cold, somewhat harsh

4:02

and withholding of her approval. Oh

4:05

no. Yes.

4:06

Dave remembers the family watching the Ed Sullivan

4:09

show and his

4:10

mom got really irritated when Ed

4:12

Sullivan asked the audience to applaud for

4:14

a musical act before they performed.

4:16

You know, like, now welcome to the stage,

4:18

blah, blah, blah. Apparently her

4:20

take was that you should only get applause

4:22

based on merit. Oh. So

4:25

any kind of pre-applause was not yet earned. She's

4:27

a dream crusher. She's a dream crusher. Yikes.

4:31

They've got, she is now part of his career,

4:33

like. His shtick. Yes,

4:36

they've worked it out, but. Well, I'm glad

4:38

for that, but wow, that's a tough mom.

4:41

Tough mom.

4:42

His dad, Harry, was good natured

4:44

and outgoing and had

4:45

a great sense of humor.

4:47

Dave and his father shared a sense of humor. They

4:49

bonded

4:49

over it. He discovered that

4:51

he and his father kind of had this similar

4:54

sense of humor when he was about six and

4:56

they both laughed and got the low-key, dead-pan

4:59

comedy routines,

5:01

listening to the radio, listening to comedians

5:04

on the radio back in the pre-TV

5:06

era. Unfortunately, Harry

5:08

was also an alcoholic who

5:11

was clearly frustrated by his position in

5:13

life. Oh, no. So it sounds

5:15

like everything was good and stable

5:18

and predictable until Dave was about 12 years old. So

5:21

that year, a couple of things happened. Up

5:24

to that point, Harry, the dad, had

5:26

been a partner at a local flower shop that

5:28

had done very well,

5:30

but then Harry had

5:31

a major heart attack and his business partner

5:33

decided to sell his share of the store

5:35

while Harry was recovering. Oh, that's

5:38

dirty. Harry couldn't afford

5:40

to buy him out because he had large medical

5:42

bills.

5:43

So Dave says at that time, from that

5:45

point on, everything started to go away.

5:48

It was awful. What vocate do you send

5:50

someone to say, you ruined

5:52

my life? Yeah, right. Wow, that's

5:54

terrible.

5:55

Harry's disappointments in life had

5:57

a big impact on young.

5:59

He remembers that his dad actually seemed

6:02

happiest and most at ease when he

6:04

was hosting a meeting at the Indiana Flower Association

6:06

or him seeing a church potluck

6:08

dinner Anything where he could be in front

6:11

of people performing and telling jokes

6:13

this obviously made an impact Dave

6:15

would tell a biographer he loved doing

6:17

that more than his actual job My dad's

6:20

life did not work out the way he wanted it to

6:23

On Mark Marin's WTF podcast.

6:25

He said my father could have easily done what

6:27

I have done and I wish he had oh

6:31

so when Dave was 12 his father let him

6:33

have a sip of scotch and soda at a Christmas

6:35

party and

6:36

He would tell Howard Stern

6:38

that after that

6:39

he continued drinking He would sneak the

6:42

whiskey that his parents kept under the sink like

6:44

after everybody went to bed And by the

6:46

time he was in high school, he was getting drunk regularly

6:49

Dave had jobs when he was young

6:51

he bagged groceries throughout high school He

6:54

went to Ball State University for college

6:56

And I don't know how that's not just a an

6:59

entire catalog of jokes in the David Letterman

7:01

oeuvre. Maybe it is I I'm not

7:03

a scholar of David Letterman He

7:05

was a radio DJ during his college years

7:07

and he would get in trouble and sometimes fired

7:09

from stations for Refusing to follow

7:12

the rules or for playing pranks

7:14

on the wrong people at work He

7:16

also was continuing to drink. I'm sure that was

7:18

about to say that couldn't have been a Overall

7:21

positive contribution to job stability.

7:24

Yeah, he pledged Sigma Chi

7:26

In college but said it was mostly an excuse

7:28

to drink as much beer as possible

7:31

He was very reserved socially and he was reluctant

7:33

to let anyone really get to know him One

7:35

of his fraternity brothers would later say

7:38

Dave didn't let people close to him I

7:40

asked him about it and he said if they got to know

7:42

me they wouldn't like me

7:44

Listen, don't be upset if I don't go to the parties.

7:47

Oh, well, that's kind of sad. Mm-hmm kind

7:49

of relatable though I felt that way, you

7:51

know at a certain when you were younger Yeah,

7:53

when I was a thing when I was a young person if you

7:55

got to know me you wouldn't like me Mm-hmm. I

7:58

think a lot of people feel that way at times I

8:00

think this is kind of foundational to Letterman.

8:03

I think there's a real loathing, self-loathing. So

8:06

Dreamcrusher Mom, alcoholic dad,

8:08

packed with self-loathing. This story is gonna go awesome.

8:11

It's really good. So let's talk about

8:13

the first time that David Letterman got married.

8:17

It was the summer of 1968. No.

8:19

And Dave had been dating his college sweetheart,

8:22

Michelle Cook, for quite some time.

8:25

She decided that it was time for them to get

8:27

married.

8:28

So she told him that either he married her or

8:30

she was going to move on with her life without

8:32

him. Okay, fair. Very straightforward,

8:35

Midwestern. She had just graduated.

8:37

She was a year ahead of him. And Dave was finishing

8:39

up his last year of college while working as a weekend

8:42

weatherman at a local television station. Sounds

8:44

right.

8:45

He panicked when she gave him this ultimatum.

8:48

He would say later, I could not lose her. That

8:50

horrified me. Unfortunately,

8:53

the other thing that horrified Dave was

8:55

the idea of telling his parents that he was going

8:57

to marry Michelle. He would say

8:59

they didn't like her, but they didn't really know her.

9:02

So, what happens? Oh my God.

9:06

He tried to find a solution

9:08

that would make both Michelle and his

9:10

parents happy. So he

9:12

decided to get married and not tell his parents.

9:15

Secret wedding? Secret wedding. Bingo.

9:18

Secret wedding. So, Michelle's roommate

9:21

drove the couple to a house not that far from

9:23

campus. Dave, of course, had been

9:25

drinking heavily prior to being picked

9:27

up. And when they arrived, a justice

9:29

of the peace answered the door.

9:31

Dave introduced himself with a joke.

9:34

Boy, am I glad to see you. These broads

9:36

picked me up out here on Highway 36. We

9:39

started talking and the next thing I know, they say,

9:41

hey, you're kind of cute. Let's go get married.

9:44

Hell, I've never seen these broads before in my life.

9:47

Oh, no, no, no. Yeah,

9:49

the justice of the peace did not even smile

9:52

at this saying, are

9:54

you David Letterman?

9:55

He said yes. And

9:57

then the JP, the justice of the peace looks

10:00

that the two women and says which one

10:02

of you is Michelle Cook. David continued

10:04

with his jokes, definitely warming

10:08

things up. When the justice

10:10

asked if either had been married before,

10:12

Dave helpfully replied six times.

10:15

Oh,

10:16

oh, the drunk

10:19

groom aged probably 21. After

10:22

the wedding, Michelle stayed in Muncie, Indiana,

10:24

and Dave lived with his parents for the summer because

10:26

he was working at a local television station

10:28

back home.

10:29

He promised Michelle that he would tell his parents

10:32

and this is all terrible,

10:35

and that he would then find the two of them a place to

10:37

live for the following semester. Oh, sure.

10:40

Michelle, as you would, is, you know,

10:42

calling Dave and she did not hear from

10:44

him for an entire month. Wow,

10:47

secret wife. She finally drives

10:49

to his house,

10:51

I guess knocks on the door and

10:54

parents open like, yeah, and

10:57

they have no idea. They have no idea.

10:59

Holy cat. Their son is married and

11:01

that she is their daughter in law.

11:03

Dave would tell his biographer, I lived

11:06

in terror that my parents would find out.

11:08

You can't keep things like that hushed up. No,

11:11

Dave, you can't. So

11:14

one night he arrives home to find that Michelle

11:16

has arrived there and has told his parents

11:19

that they are married.

11:20

His mother assumed that she must be pregnant.

11:23

Sure. She was not.

11:25

Dave would say I walked right into a shitstorm.

11:28

My parents, my parents, your own

11:30

making of your own making. My

11:32

parents were horrified and depressed. They were

11:35

angry. Why and how and what

11:37

was going to happen and on and on.

11:39

They were really hurt, deeply hurt, and

11:41

they had every right to be. Well, Dave

11:44

does eventually graduate, married

11:46

Dave, and he and Michelle moved into

11:48

his hometown and

11:49

like a few blocks away from his family. Michelle

11:52

worked as a buyer at a department store and Dave

11:54

worked at a television station as the weekend

11:57

weatherman. And he, you

11:59

know, made a lot of. ripples because he was a funny

12:01

guy, as we all know. He

12:03

was very informal on the air and

12:06

he would ad lib jokes. It just,

12:08

it really worked. He was a great television

12:11

personality. So Huzzah,

12:13

the full-time weatherman position opens up

12:16

and Dave is very excited to go and apply for

12:18

that and audition for that. And he did not get the

12:20

job. Oh no. It

12:22

rained on his parade. Ah, look

12:24

at that.

12:26

So this sort of got him thinking more

12:28

about Hollywood. Clearly like television

12:30

was something he was enjoying. Audiences

12:32

liked him. But is the weatherman,

12:35

what he wanted to do with his life? I don't know. He's

12:37

going to be a big, big star. So

12:40

he remembers watching Carson when

12:42

Carson was doing the Karnak, the magnificent

12:45

routine. So Ed McMahon would set

12:47

up jokes and then Carson

12:49

would do the punchline and Dave

12:51

would sit there making up different

12:54

punchlines. Like this was

12:56

kind of, yeah, he was sort of working

12:58

on a bit of his own work. He

13:02

was not yet ready to make the leap

13:04

to Hollywood. So he went to work

13:06

at a radio station like he'd done for a lot of

13:08

his college career. Again, becoming

13:10

very popular for dry humor,

13:13

quick wit. His father's

13:15

drinking had become a serious problem.

13:18

And at one point his

13:19

mother actually told him that she was going to divorce

13:21

his father. Oh, wow. She

13:23

thought it over and instead decided

13:26

to call AA, Alcoholics

13:28

Anonymous. Harry agreed to

13:30

give it a try. He quit drinking. He started

13:32

hosting meetings. Oh, wow. Solid

13:34

move, mom. Yeah, yeah. Well, and Dave says he wanted

13:38

me to come to one of the meetings. I

13:40

did. And by God, he had taken over. He

13:42

would write jokes. It was like the Friars Club.

13:45

He just liked being the center

13:46

of attention.

13:48

Dave was stunned at

13:50

how much his father thrived in that situation

13:52

and how much he loved telling jokes to his audience.

13:55

But soon after that meeting that his father

13:57

had invited him to, Harry had another heart.

14:00

attack and this one was fatal. Dave

14:03

says I just felt like he never quite got

14:05

to do what he wanted to do. So

14:08

that was a very strong observation for

14:10

me. I really wanted to make good on my personal

14:12

commitment because I know it was probably

14:14

the same as my father's personal commitment, but

14:17

he just never had the opportunity or the pathway

14:19

to fulfill it. Michelle

14:21

was just a huge cheerleader

14:23

for Dave to pursue comedy. She

14:26

had long encouraged him to move

14:28

to Hollywood

14:30

and until his dad died, Dave

14:32

really just hadn't felt like he could. It

14:35

didn't help that his mother, Dorothy,

14:37

was a bit of a soul crusher. She was

14:39

super skeptical. She did not think that comedy

14:41

was a real job. Well, I mean, a

14:43

lot of moms don't. Yeah. So,

14:46

you know, Michelle though was there and really

14:49

counterpoint. I think he just opted to listen to

14:51

Michelle and he would say later,

14:54

I don't know if I could have done it without her of

14:56

moving to Los Angeles. So

14:59

let's take a break right here and when we come

15:01

back, we are going to watch David

15:03

Letterman burn his marriage down

15:06

in Hollywood. It's what we live

15:08

for here on Trashy Divorces. See

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16:51

It took Dave less than two weeks

16:54

after arriving in Los Angeles to go

16:57

to the comedy store. And soon afterwards

16:59

he was on the stage regularly.

17:02

You know, I have to mention the comedy store is the

17:04

same location. The former Ciro's

17:06

where so much of old Hollywood has happened.

17:09

God, I love the spider webs that happen in

17:11

this show. Well in this incarnation

17:13

as the comedy store, this was the place that

17:16

you wanted to perform. If you were trying to make it

17:18

as a comedian in the seventies, bookers

17:21

went talent scouts went and it was

17:23

the best place to network and collaborate with

17:25

other aspiring writers and comedians.

17:28

Dave told Mark Maron, the comedy store

17:30

was completely exciting and completely different

17:33

from anything culturally or socially

17:35

I had been part of in Indiana.

17:37

Dave's style of standup stood out from

17:40

everybody else in that milieu. He

17:42

was relaxed and he was charming. Whereas

17:45

others tended to be very jittery or high

17:48

energy or

17:49

just anxious and amateur. You think

17:51

it could have been the drugs of the seventies? I

17:53

was going to suggest that cocaine may have played

17:55

a role for a lot of people, but

17:58

Dave would be up there. He'd, you know, tell a

18:00

joke and then like crack his neck or

18:02

maybe he'd whistle you know like just whistle

18:04

a little song for a second like

18:06

just very toned down low-key and

18:09

very funny.

18:10

As good as the comedy store was for young

18:12

comedians

18:13

it unfortunately did not pay its performers.

18:17

Michelle was supporting the couple financially

18:19

she was working at a department store and

18:21

Dave of course had this traditional Midwestern

18:23

upbringing so it

18:26

graded on him that Michelle was

18:28

the breadwinner for the family. He

18:30

would say my wife was working while I was on the playground

18:33

shooting baskets feeling like a bum. Eventually

18:36

he did land a job with a steady income

18:39

writing jokes for Jimmy Walker. Oh wow

18:41

okay. Yeah he had broken out on good

18:43

times

18:44

and Jimmy had hired a couple other aspiring

18:46

comics to help him write jokes. Like you. You

18:49

may have heard of one Jay Leno and

18:52

one Elaine Boosler. Wow. I know

18:54

this is really quite the the milieu.

18:57

Hey Alicia what do you think happened

18:59

when you've got 20-somethings

19:01

teaching themselves to be performers by

19:04

staying out in comedy clubs until the wee

19:06

hours and drinking too much?

19:08

Probably drugs mixed in there too. That's

19:11

right they hook up. Oh no.

19:13

And Dave regardless of things

19:15

with Michelle who had a steady job

19:18

was no exception. Dave

19:20

cheated on Michelle regularly and had

19:23

quite the reputation as a ladies man

19:25

in the stand-up scene during the 70s. In

19:28

addition to that Dave's drinking was isolating

19:31

the

19:31

couple from you know like

19:33

the friends Michelle was able to make in Los Angeles.

19:36

Steve O'Donnell one of his more significant

19:39

writers during his late night career would say

19:42

of Dave he said that his first wife Michelle

19:44

was constantly complaining they lost every

19:46

friend they had because Dave would drink and start

19:48

making jokes about what's wrong

19:50

with them. No you can't do that.

19:52

I mean not on the regular.

19:55

Yeah super isolating. Wow.

19:57

Super terrible. Hal Gurney, Dave's

19:59

law director said that he felt

20:02

that Dave didn't want the kind of lifestyle that

20:04

he and Michelle had both grown up with. Alienating

20:07

your circle of friends is a pretty good way to

20:09

do that. Yeah.

20:10

Dave told him that he couldn't stand that

20:13

Michelle ironed

20:14

and folded his underwear and socks.

20:16

Oh wow. That's a level of commitment. So

20:19

yeah, Hal says it would be so middle-class.

20:22

It would be like people you'd expect to work in an

20:24

insurance agency.

20:25

He wanted to be a comic.

20:27

Comics don't have their underwear ironed.

20:30

Fair point. Yes. So it

20:32

is important to note that Dave was still drinking

20:34

quite heavily at this time and this

20:37

inevitably contributed to plenty

20:39

of bad behavior and the dissolution

20:41

of his marriage. It wasn't until

20:43

he was 34 that he would finally stop

20:46

drinking. He'd been told for years

20:48

when he went to get his annual physical that his

20:50

liver was swollen

20:51

and that's a pretty young age to...

20:53

Well if you had been drinking since you were what, 12? 12. I

20:56

guess that's a good point. Yeah, that's 22

20:58

years of nipping scotch

21:00

under the sink and then just moving

21:02

it to the comedy club. Yeah,

21:05

and so it really...

21:07

He quit drinking because he was afraid it would

21:09

hurt his career.

21:10

Not to save his mar... Right? Not

21:13

to save his liver. Not to save his

21:15

liver and not to save his marriage. Like his priorities

21:17

were clearly what they were.

21:20

So yeah, once he

21:21

got back on television, he

21:23

did not want to screw that up.

21:25

Michelle and Dave divorced in 1978.

21:29

Ultimately, Dave took responsibility

21:31

for this, saying,

21:32

I went a little nuts and misbehaved

21:34

and it came apart,

21:36

but I think it's my own doing or my own

21:38

undoing. In 2010,

21:40

Vanity Fair quoted him saying,

21:42

for what I put her through, I should burn

21:44

in hell for the rest of my life. It

21:46

was just me being a dork. Hey,

21:48

young girls! Well,

21:51

at least he has some self-reflection

21:53

and awareness now. Perhaps.

21:55

Now, yes, as we shall see. Sorry,

21:59

Michelle. Well, you didn't deserve that, sweetie.

22:02

Just wait. Oh no. Yeah,

22:04

it doesn't particularly improve. The

22:07

story doesn't get better. No. So

22:09

the next woman who would have a significant impact

22:12

on Dave, both personally and professionally,

22:14

was comedy writer Meryl Marko. These

22:17

two were together for about a decade, and Meryl

22:19

was his major collaborator when he was

22:21

establishing his career in

22:23

late night.

22:24

The two met at the comedy store in 1978. They

22:27

both claim that they were only friends

22:29

until Dave split with Michelle. Sure.

22:32

But Meryl also tells the story of going

22:34

with him to Michelle's house to pick things

22:37

up.

22:37

So clearly, whoa. Meryl

22:41

said that when she first saw him, he was

22:43

not her type.

22:44

Her last boyfriend had been a very artsy

22:47

kind of guy.

22:48

Dave was dressed casually in

22:50

sneakers, and he seemed like a frat guy,

22:52

which he had been. She recalled the first

22:54

time she talked to Letterman, saying,

22:56

"...he was the kind of person I would have never

22:59

been friends with, but he was cute."

23:01

Meryl was sophisticated and extremely

23:03

intelligent.

23:05

She didn't have time for jokes that she felt

23:07

were silly or unworthy of her talent.

23:10

She disliked most comedy on television

23:12

during this period, but when SNL premiered,

23:15

she finally found something she did like, saying,

23:17

"...it was the first show I saw that made fun of

23:20

TV as a form.

23:21

Before that, TV really didn't see

23:23

itself."

23:24

Dave himself had a very different impression

23:27

of Meryl from the one Meryl had of Dave. Oh,

23:29

yeah? He says, "...she

23:31

looked... The term used to be preppy.

23:33

I was very attracted to her. She

23:35

looked like she was from the East Coast, and her jokes

23:38

were very heady, much smarter than

23:40

what you thought you were getting at Open Mic Night."

23:42

When they met, Meryl was writing a pilot,

23:45

and she had gone to the Rollins Joffee office

23:47

to pitch the idea. At the meeting,

23:49

the agent she was talking to told her that

23:51

one of his clients, a guy named David

23:53

Letterman, had just said nice things about

23:56

her. Meryl asked,

23:58

"...I know, Dave. Yeah,

24:01

and the agent said that he thought you were sort

24:03

of special. Oh, well, that's

24:05

nice So after this meeting she calls

24:07

the comedy store to find out when Dave will

24:09

be doing his set that night It

24:11

was of course 12 20 a.m. Oh,

24:13

no. Yeah one of those so she goes there for his 12

24:16

20 in the morning set and

24:18

After you know, it went well.

24:20

He appears next to her and they sat together.

24:23

They did not talk

24:24

Because Robin Williams was on stage telling

24:26

his jokes Wow Can

24:28

you believe it though? That means he had the 1230 slots

24:31

like it's so weird

24:33

Neither of them wanted to seem interested

24:35

in the other they were both trying to play It

24:39

didn't take him long to ask her on a date

24:41

They quickly became involved romantically,

24:43

but perhaps even more significantly they

24:46

became professional allies and this will

24:48

just propel his career dramatically

24:52

Meryl also had always been adamantly

24:54

opposed to getting married or to having children Perfect

24:57

for Dave newly divorced Dave was

25:00

like heck Yeah, I am in

25:02

no hurry to walk down that aisle again

25:04

soon. Did you hear I didn't even tell my

25:06

parents about the first one

25:10

Dave's agents soon were telling him

25:12

that he had way more potential

25:14

to work in television

25:16

than in stand-up

25:17

Meryl would help him with pitches for shows

25:19

and they would write pilots together

25:21

And she also wrote jokes for a stand-up

25:24

act while he was still trying to break

25:25

into television Dave would say

25:27

she was a great education for me. What

25:30

kind of education did you give her Dave? Mm-hmm?

25:33

We'll see So as

25:35

mentioned earlier Dave had established himself

25:37

as something of a heartthrob at the Comedy Store

25:40

Many people did not understand his attraction

25:42

to Meryl Sandra Bernhardt said

25:45

of Meryl Her writing

25:47

was yeah, the story has

25:49

everyone

25:50

her writing was smart and original But

25:52

it was like that's who Letterman

25:54

is dating. She was kind of androgynous

25:57

a guy's girl, which maybe

25:59

that's what he liked liked about her. Meryl

26:01

got a job. This is, oh my God, this is

26:03

really, this anecdote is so,

26:07

so David Letterman.

26:08

So Meryl gets a job writing on Mary Tyler

26:11

Moore's variety show, Mary.

26:13

When Meryl walks into the writer's room looking

26:16

around, she notices that David

26:19

Letterman is on the list of cast

26:21

members. These two were spending

26:23

every night together and he had not mentioned,

26:26

you were joking. I'm not. He had

26:28

not mentioned

26:29

that he was working on the same show that

26:31

she would be working on. She would later

26:33

say that this was a quote portent of

26:36

many things to come. There's

26:38

always a portent. This is a guy who just

26:41

keeps his trap shut.

26:44

As we all know,

26:45

Dave did make it to television.

26:47

He appeared on The Tonight Show with Johnny Carson 22

26:50

times and then began guest hosting

26:53

for The Legend.

26:55

In 1982, Late Night with David

26:57

Letterman debuted and this

26:58

of course made him a national figure,

27:01

household name.

27:02

He and Meryl were still together and he made

27:04

her the head writer on the show.

27:05

She was the first head writer. Oh, wow. Okay.

27:08

It was Meryl who originated classic

27:10

bits like Stupid Pet Tricks. Stupid

27:14

Pet Tricks. Stupid Human Tricks. Yeah.

27:17

Viewer male. She was also responsible for

27:20

a lot of like just the silliness

27:22

and you know, there were like unscripted remotes.

27:25

He went to a store one time called Just Bulbs

27:28

and he would just like interview the employee. So

27:30

what do you sell here at Just Bulbs?

27:36

In the course of her career on Dave's Late

27:38

Night shows, Meryl was nominated

27:40

for six Emmys and won three.

27:43

In 2020, she was the recipient

27:45

of the Writers' Guild of America's

27:47

Patti Shajewski Laurel

27:49

Award for Television Writing Achievement. It's

27:51

the highest award given for television writing.

27:54

Well, good on Meryl. They were

27:56

together for most of the eighties. They worked and

27:58

lived together. She She told the New York

28:00

Times in 2009, "...I can

28:02

remember a few times following him into the bathroom

28:05

post-rehearsal pre-show

28:07

while he showered and got ready. I stood

28:09

there reading him lists of jokes or re-written

28:11

ideas for things to do on the show."

28:14

Then she added, "...I guess over the years

28:16

there has been an assortment of other women

28:18

who continue to have that sort of access to

28:20

him,

28:21

but from what I read it doesn't appear that

28:23

their duties include reading him joke rewrites."

28:26

Interesting. In 1986,

28:30

Meryl and Dave were still together. This

28:32

did not stop him from beginning a

28:34

relationship with a new production assistant, No.

28:37

Regina Lasko, who came to work on

28:39

the show. They

28:40

quickly fell in love. Of course

28:42

they did. It would be two more years

28:45

before Meryl found out about

28:47

this relationship. Meryl

28:50

explains how she learned about Regina, saying,

28:53

"...I at him intercepted some letters

28:55

that came to the house and became aware

28:58

of a lot of other stuff as well."

29:01

That is some secret keeping. Yeah,

29:04

soon thereafter Meryl changed her phone number.

29:06

She drew a cartoon of a talk show host

29:09

sitting at his desk with a big slash through it

29:12

and put that on her front door.

29:14

So soon after that Regina would leave

29:17

his show to work for Saturday

29:19

Night Live. The two of them stayed a couple. Meryl,

29:22

meanwhile,

29:22

departed for the warmer climes of California

29:25

to continue as a comedy writer.

29:27

Good on her.

29:28

In 2008, Dave told

29:30

Rolling Stone about the end of his relationship

29:33

with Meryl, saying,

29:34

It

29:38

seems like I've heard that line before. Are

29:41

you gonna rot in hell for ruining Meryl too?

29:43

Come on, Dave. Happily did not ruin

29:45

Meryl. Randy Cohen, a longtime

29:48

writer on the show, said, When Meryl left

29:50

the show, the show, in my view, really suffered.

29:53

She brought him along in a certain way where

29:55

he saw, even if they weren't his favorite pieces,

29:57

he saw the value of doing them.

29:59

else could be as unrelenting.

30:02

One of her many fine qualities. If

30:04

it were a piece she enjoyed, she would fight

30:06

for it.

30:07

Years after their breakup, an interviewer would

30:09

ask Dave about Merrill's impact on

30:11

the show and

30:12

he replied simply, without her,

30:15

you and I would not be sitting here. That's right. I'm

30:17

glad you get that, Dave. We're going to take one

30:20

more quick break

30:21

and when we come back, we're going to talk about

30:23

David Letterman's weird stalker situation

30:26

which I had completely forgotten about.

30:29

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Yeah, from the late 80s

32:02

to the late 90s, close to a decade,

32:04

Dave was the subject of obsession

32:07

by a disturbed woman named Margaret

32:09

Mary Ray, who relentlessly

32:11

stalked and pursued him. So

32:14

she believed that she was romantically

32:16

involved with him. I do kind of remember

32:18

this. And she repeatedly broke into his

32:20

house. She would camp out on his tennis

32:22

court. She stole his Porsche one time.

32:25

No!

32:27

She was repeatedly arrested for this

32:29

behavior as one would expect. But

32:31

she would identify herself as Dave's wife

32:34

and tell people that her son's name was David Letterman

32:36

Jr. Oh

32:39

no!

32:39

I mean, this was such like

32:42

a New York story in some ways.

32:45

Very strange time, the 80s

32:47

and early 90s. She once told reporters

32:49

that she left cookies and an empty bottle

32:52

of Jack Daniel's whiskey in the foyer of

32:54

Dave's house during one of her visits.

32:57

Is in quotation marks.

32:59

Wow.

33:01

The world obviously was

33:03

fairly naive at this

33:04

time still about the dangers that stalking

33:06

poses to celebrities. So

33:09

it was sort of treated as a less serious

33:11

matter than it could have been. She

33:13

was frequently on tabloid magazines and she

33:15

was the subject of late night jokes,

33:18

including some from Dave himself.

33:20

He never said her name on the

33:22

air, but it was a

33:24

public spectacle.

33:26

One such joke was including her in

33:28

one of his top 10 lists. No. His

33:31

famous top 10 lists.

33:33

In his top 10 things I have to do before

33:35

I leave NBC,

33:37

number one was send change of

33:39

address forms to that woman who keeps breaking

33:41

into my house. Sounds

33:43

like the number one. Did you ever notice

33:45

on the top 10 list that number two was always funnier

33:48

than number one? I don't know if I specifically

33:50

noticed that. Go back and watch any top 10 list

33:53

from David Letterman. I'm sure there are YouTube

33:55

compendiums

33:55

of them. Number two is

33:58

always the punchline, never number one. Interesting.

34:01

Margaret Mary Ray would spend over 34 months

34:03

in jail and in psychiatric hospitals

34:05

for stalking Dave.

34:07

She was diagnosed with schizophrenia during one

34:09

of those stints, but like as

34:12

soon as she was released she would stop taking her

34:14

anti-psychotic medications. It

34:16

just turned into this cycle. She didn't

34:19

like how the drugs made her feel. She didn't

34:21

think she needed them. Dave

34:23

was not her only victim. She was

34:26

also obsessed, this is so weird, with astronaut

34:28

Story Musgrave.

34:30

She harassed him for

34:31

four years with phone calls, letters, and

34:33

sending him unwanted packages.

34:36

She once went to his home and turned on all the

34:38

outdoor faucets.

34:39

Why? Well,

34:40

when she was arrested she told police,

34:43

I love him and want to spend the rest of my life

34:46

with him. Which is why I'm just gonna waste

34:48

his water and the drought. What? And

34:50

poor Dave. Dave.

34:52

No, I don't mean to make light because

34:55

Margaret Mary Ray

34:57

met a deeply tragic end.

34:59

On October 5th, 1998

35:02

she wrote out a suicide note that read, I'm

35:04

all traveled out. I

35:05

chose a painless and instantaneous

35:07

way to end my life in the valley I loved.

35:10

She then knelt down on the tracks of the

35:12

Denver and Rio Grande Western Railroad

35:14

in front of an oncoming train and

35:16

was killed instantly. Dave

35:19

released a statement saying this is

35:21

a sad ending to a confused life.

35:23

That is tragic. Okay,

35:25

so let's get back to

35:28

the woman who would become his second, who will become his

35:30

second wife. Regina. Final wife,

35:32

yes. Okay, so Meryl's out, Regina's

35:34

in.

35:35

Meryl's out, but she's not done snarking.

35:37

Oh no. We'll get to it.

35:40

Although Dave and Regina were together for

35:42

many

35:42

years, they were very purposeful about

35:44

staying out of the spotlight. They were rarely

35:46

seen in public. He really has

35:49

just been such a closed book when it comes to

35:51

his personal life.

35:52

In fact, Dave stayed away from any talk

35:54

about his personal life whenever

35:56

he could.

35:57

The closest anyone got to him, including anything he

35:59

could.

35:59

personal on his show was when his mother,

36:02

Dorothy Dreamcrusher, made

36:04

appearances. Dreamcrusher

36:07

no more made appearances on his show

36:09

and she became an unlikely celebrity in

36:11

the 90s. She went to Lily Hammer

36:14

to cover the Winter Olympics in 1994 for the late

36:16

show and she also wrote a cookbook

36:21

called Home Cooking with Dave's Mom.

36:25

But when it came to his love life, silence.

36:28

Absolute silence.

36:29

A long time Letterman Observer said that

36:32

they believe that Dave's inherent self-loathing

36:34

and lack of confidence informs the women

36:36

he chooses and the way he conducts himself.

36:39

By his own admission, Dave is insecure,

36:41

guilt-ridden, and self-pitying. Like

36:44

you would expect from a Midwestern boy.

36:46

That

36:47

is quite a description. So this

36:49

is the long time Letterman Observer,

36:51

a quote here, quote, he favors unadorned

36:54

women and at the same time women who are at

36:56

the reach

36:56

of his demonically low

36:58

self-esteem. Wow, that's

37:01

a descriptor. The 2010

37:03

Vanity Fair article called Big Trouble

37:05

at 1135 calls Regina

37:07

Lasko the archetypal Letterman

37:10

woman. Extremely smart, rather plain

37:12

in appearance and absolutely silent

37:14

when it comes to him. This

37:16

is fascinating. It

37:18

surprised the world when the couple welcomed

37:20

a son in November of 03. Dave was 56 at the time

37:23

and Regina

37:25

was 43. They

37:26

named their son Harry Joseph after

37:28

David's father and still they did

37:31

not marry. At this point they've been together

37:33

a while since 86. Yeah.

37:36

Yeah.

37:37

So they lived in Westchester, New York.

37:40

Regina and Harry were rarely seen in public.

37:43

Some guests, Julia Roberts in particular,

37:45

would, you know, poke some fun at Dave

37:47

about not marrying his extremely

37:50

long time

37:51

girlfriend and mother of his child.

37:54

Dave would respond by being visibly uncomfortable

37:56

and making sardonic

37:57

jokes. In 2005,

37:59

I also

38:02

never was aware of this.

38:04

There was a plot to kidnap Harry.

38:06

That was discovered. The would be

38:09

kidnapper was a man who worked as a painter

38:11

at their Montana ranch.

38:13

He was planning to demand $5 million in ransom.

38:16

Fortunately, the plot was foiled before

38:18

anything happened to their son.

38:21

The perpetrator was sentenced to 10 years in

38:23

jail, but he broke out of jail in 2007. No.

38:27

And was then given an additional decade. He

38:29

was freed in 2018. Good

38:31

Lord. How do you break out of jail in 2007 anyway?

38:37

In 2009, Dave and Regina married,

38:39

and you'll be surprised, a secret

38:41

ceremony. Harry was five years old at

38:44

the time he was there. Huzzah.

38:49

When Dave told his viewers about the marriage

38:51

and how he had quote, avoided marriage

38:53

for 23 years. Right. He said

38:55

quote, I secretly felt that men who were

38:57

married admired me. Like I

39:00

was the last of the real gunslingers.

39:01

You know what I'm saying? The

39:03

real gunslingers. Good

39:05

Lord. Okay. Now

39:08

we get to the very famous extortion attempt

39:10

and the resulting public sex

39:12

scandal.

39:13

This story really is a real

39:16

ride if it's a complete secret or

39:18

everyone knows about it. I mean. Extortion

39:20

plot?

39:21

Okay. So again, he married in March

39:24

of 2009.

39:25

Pretty

39:28

sure. In October 2009, David

39:30

Letterman found himself embroiled in

39:34

a messy and embarrassing sex scandal.

39:37

On October 1st, the members of the live studio

39:39

audience for the late show had absolutely

39:42

no idea what they were about to witness.

39:44

Neither did millions of people watching at

39:46

home.

39:47

Dave had been having an affair with a staffer

39:50

on the show, Stephanie Burkett, for

39:52

several years. While he's with

39:54

Regina? Yes. And they have a five

39:56

year old kid. Okay.

39:59

And recently he had been the... victim of an attempted

40:01

extortion and blackmail.

40:03

So it turns out that Stephanie Burkett had

40:05

a boyfriend. Sure. A guy named Joe

40:07

Haldeman. This guy's a television

40:10

news writer, director and producer at CBS

40:12

News,

40:13

like not a slouch in his own career. He worked

40:15

on 48 hours at the time.

40:17

He's won eight Emmy Awards for

40:19

broadcast journalism. Like smart enough

40:21

to know better. Smart enough to know better. Anyway,

40:24

he finds out about the affair,

40:26

became enraged. Stephanie

40:29

said that she was ending the relationship. She did

40:31

not end the relationship.

40:33

So Joe sends proof of the affair to

40:35

Dave and tells him that

40:36

if he doesn't pay $2 million, he's

40:38

going to expose it to the world. No, 2

40:41

million bucks. 2 million bucks. Dave,

40:43

instead of forking over the money,

40:46

decides to get the police involved. And once

40:48

the arrest was made, he took control of the

40:50

media story by coming clean

40:53

on national television.

40:54

He did not deny having sex with subordinates.

40:57

He admitted that he had done terrible, terrible

41:00

things. That's a quote.

41:01

It seems like we've heard that quote before.

41:05

Yes, he cops to that a lot.

41:07

Bad, bad things. Apparently

41:09

he just continues to do bad, bad things.

41:11

He said, quote, I have had sex with

41:13

women who work for me on this show. The

41:16

audience laughed nervously. And Dave

41:18

went on to say that he called his attorney and

41:20

then set up a meeting with the blackmailer.

41:22

The police got involved

41:23

and Joe walked right into the sting

41:25

operation and

41:27

blah, blah, blah, the rest is history. Dave

41:29

tried to infuse some humor

41:32

into this fairly awkward confession,

41:34

saying, I know what you're saying. I'll

41:37

be darned. Dave's had sex. He

41:41

continues, that's what the grand jury said also.

41:43

Really? You have had sex?

41:47

Of course, the scandal caused a media

41:49

storm and there were jokes and news stories

41:51

and everybody was looking to find

41:54

interns who had salacious accounts of

41:56

having had an affair with Dave. Jay

41:58

Leno, old co- worker made

42:00

a lot of jokes about the situation, including,

42:04

this is very mean-spirited, you

42:06

know the best way to get Letterman to ignore you?

42:08

Marry him. He will not bother

42:11

you. He won't look you in the eye. Oh,

42:13

Regina. Joe Haldeman

42:16

was sentenced to six months at Rikers Island

42:18

prison.

42:19

While serving his sentence, this is so weird,

42:21

he was nominated as a producer of

42:24

a 48-hour segment regarding Amanda

42:26

Knox for an

42:27

Emmy. Wow.

42:28

After the extortion plot became public,

42:31

revenge of Meryl, Meryl Marko

42:33

weighed in on the scandal by writing on her blog,

42:36

Oh, goody. As you can imagine, this

42:38

is a very emotional moment for me

42:41

because Dave promised me many times

42:43

that I was the only woman he would ever cheat

42:45

on. She

42:47

continues, we were together for 10 years,

42:50

though I know that it's a vague definition

42:52

of the word together since he was apparently

42:54

with Regina for the last two of those years

42:57

and

42:57

to my knowledge none of us were involved in

42:59

a polygamous cult. When a journalist

43:02

would later ask Meryl how Dave had

43:04

managed to keep his affair with Regina

43:06

a secret, this

43:08

is very interesting. She says, Dave has

43:10

several homes. He has a television

43:13

show and production and many meetings to

43:15

attend, some of which require travel. Add

43:18

to that the fact that he actually has numbers

43:20

of clinically diagnosed crazy people stalking

43:23

him and you've got the makings of a package

43:25

full of enough wool to make mittens, sweaters,

43:28

scarves, and matching blindfolds

43:31

for as many people as you have on your gift

43:33

giving list. Fair point.

43:36

She continues, to make things more convenient

43:38

during the last few years of our relationship,

43:40

I was spending time in LA trying to start

43:42

projects of my own and was

43:44

naive enough not to be especially paranoid

43:47

because not only did he and I continue

43:49

to work together, but I, like

43:51

Tiger Woods's wife, was under the

43:53

impression that my flawless Scandinavian

43:56

supermodel good looks were enough to keep

43:58

a man at home. She's

44:00

so good.

44:01

Many years later, in 2019,

44:04

Dave opened up about that whole chapter in

44:06

his life.

44:07

Reflecting on his relationships with women, he

44:10

said, I never had anyone in my life

44:12

sit down and talk to me, not in school,

44:14

not at home, not in church,

44:16

about how a man of age behaves

44:18

with a woman of age. It just didn't happen.

44:21

You picked it up from your buddies.

44:23

He told the interviewer that he's determined

44:25

that his son, who was at the time 16, has a

44:28

stronger character and treats women better

44:31

than he did. Well, that's a little bit of

44:33

evolution right there. Yeah, saying,

44:35

my son knows about this period of my life.

44:38

We have conversations about girls and about

44:40

his mother and how we treat her.

44:42

I don't think he will make these mistakes,

44:44

and I'm sorry, I did. I

44:46

feel a little bit better about this story. Yes,

44:49

there is evolution, there is growth. David

44:52

Letterman may have

44:54

decided to grow up. Let's

44:56

see though, we're going to check on him kind

44:59

of to today. In 2013, Dave

45:01

sat down with none other than Oprah Winfrey

45:04

and revealed that he had been seeing a psychiatrist

45:07

once a week to try to become a better person.

45:10

He said, I want to be a good person. For

45:12

a long time, I thought I was a good

45:14

person, and yet I was capable of behavior

45:16

that is not consistent with that. My

45:19

life is fun and full of joy now. I

45:21

only pretended that before. Isn't

45:24

that really the sum of it? We all

45:26

want to be good people, but wow,

45:28

the thing that keeps us all in common is

45:30

that our lives are so messy. Yes.

45:33

Everything is messy.

45:33

Yeah, so Oprah, of course, asked

45:36

him about the affair and the extortion

45:38

scandal and all of that stuff. He

45:40

says, he's

45:41

always very open about accepting

45:44

blame for his own bad behavior.

45:46

Anyway, he says, I have no one to blame but myself.

45:49

I hurt a lot of people. I have nobody

45:51

to blame but myself.

45:52

I'm not looking to blame anybody.

45:54

I'm looking to find out why I behaved

45:57

the way I behaved. And the

45:59

light bulb goes. on. Boom. On

46:01

May 20th, 2015, David

46:03

Letterman hosted his final episode of

46:05

The Late Show with David Letterman.

46:08

In his career, he had hosted 6,080 episodes

46:10

over 33 years. He is, of

46:14

course, the longest-running late-night broadcaster

46:16

in American history.

46:18

And this, of course, was the end of an era.

46:21

In his career as a late-night host, Dave

46:23

became one of the most nominated people

46:25

in Emmy Award history.

46:27

He was nominated 52 times.

46:29

Whoa! Yup. He's won ten

46:31

of them, as well as two Peabody Awards,

46:33

and of course was a Kennedy Center honoree.

46:36

In 2018, Dave returned to television

46:38

with his Netflix series

46:40

My Next Guest Needs No Introduction.

46:43

He sat down and talked with incredibly

46:46

notable people including

46:47

Barack Obama, George Clooney,

46:49

Howard Stern, Kanye West, and Julia

46:52

Louis-Dreyfus. He's

46:54

also a frequent guest on a variety of podcast

46:56

interview shows. He's

46:58

been very honest about his mistakes

47:00

and his regrets.

47:02

He's always said that the best thing about ending his

47:04

show was that he got to spend more time with his

47:06

son. When Harry was 16,

47:09

he told the Today Show's Willie Geist,

47:11

people always say, well, you're not going to be

47:13

the kid's best friend. You're going to be his,

47:16

and I say, screw that. Look at me. How

47:18

much longer am I going to be around? I want to

47:20

be

47:20

the best friend. Then he laughed

47:22

and said, he's not keen on me being

47:25

his best friend. That's

47:28

beautiful. He followed up with at my

47:30

age, and this is no breakthrough or revelation,

47:33

but the most secure I ever feel is when

47:35

I'm around my son.

47:37

Well, this story has really come whole

47:39

circle. Sure. Little, little last

47:42

heartwarming tidbit here from the life of

47:44

David Letterman. In 2022,

47:47

he talked to Jimmy Kimmel about becoming

47:49

an empty nester. He said, Harry

47:51

is my son and all reports indicate that he's

47:54

okay. They tell me he's in college. I

47:56

thought it would be nothing, but it's devastating.

47:58

Am I the only one that feels that way? way.

48:00

And then he brought it back around to a joke saying,

48:03

I called him a week into

48:04

it. Hi, Harry. Harry, have

48:06

you met the kid who sells you weed? And

48:09

Harry says, I cannot confirm or

48:11

deny that dad. Really

48:15

relatable. We have a lot of folks whose

48:17

kids are heading off to college this

48:19

year or going back. Yup. Yup.

48:22

Yup. It's a thing. It's a tough time for a

48:24

parent. Stacy,

48:25

really well done. Thanks. I didn't

48:27

know that story was going to end like that. Sure.

48:30

I didn't know very much about that story, but

48:32

I feel like we have really taken

48:33

the journey of Dave Letterman

48:36

together. There was much I had forgotten

48:38

or just didn't know quite enough about in real

48:40

time. That is a top 10 list

48:44

of really a Trashy Redemption

48:47

arc. How many trash cans for

48:49

Dave Letterman? It's going to have to be 10.

48:51

It's going to have to be a top 10, but I guess

48:54

the second trash can is going to be the funniest

48:56

looking of them all. A hundred percent.

48:58

I don't know if anybody else has noticed that. Just

49:01

something I noticed through the years.

49:04

Yeah. It's not something I had noticed, but I'll take

49:06

your word for it. Thanks Trash

49:08

Pandas for tuning in today to that ride

49:11

of a Trashy Divorces story. Again, well

49:14

done and well done on y'all. We really

49:16

do appreciate you spending your time with us.

49:18

If you were looking for a little bit more Trashy

49:21

Divorces in your life, you can always

49:23

check us out at patreon.com

49:25

slash trashy divorces. Also,

49:28

if you were into Trashy

49:30

Royals this week over on our

49:33

side podcast that drops on Thursday,

49:35

Trashy Royals, we are launching into

49:37

the Trashy Victorians. If you

49:39

have not checked out that Royal

49:42

Ride of Naughty Nobles, if

49:44

you're looking for something for your Thursday

49:46

podcast listening, may we recommend

49:49

Trashy Royals. Again, thanks

49:51

for spending your time with us, for telling your friends,

49:54

for your kind ratings and reviews, for your

49:56

awesome emails, for your support on Patreon.

50:00

simply the best will be back this weekend

50:02

with a brand new Trashy Ride. And

50:05

until we meet again, darlings. Don't

50:07

give in to extortionists. I think that's

50:09

the lesson here. Also, keep your hands

50:12

clean. Keep those hearts trashy.

50:14

Big love, everybody. Bye. Bye.

50:17

And thanks to you for listening. Trashy Divorces is

50:19

a Hemlock Creatives production created and

50:22

produced right here in Atlanta, Georgia, by

50:24

us, Stacey and Alicia, with

50:26

a little research and writing help from the brilliant

50:29

Melissa Oh. Our art is by Sydney

50:31

V. Smith. That's SydneyVSmith

50:33

at CarbonMade.com.

50:36

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50:39

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