Comedian Tom Dreesen has seen it all.In the 1960s, the Harvey native pioneered the first interracial stand-up comedian team, Tim & Tom, with Tim Reid (best known for his later role as Venus Flytrap on “WKRP in Cincinnati”). In the 1970s, he helped lead the strike against Mitzi Shore's iconic Comedy Store. Dressen also appeared on the “Tonight Show” 61 times and served as Frank Sinatra’s opening act for 14 years.In this edition of The Big Questions podcast, Dreesen talks about his career, hanging out with Sinatra and his friendships with David Letterman and Jay Leno.Below is an excerpt of our wide-ranging conversation, but you can listen to the full episode on iTunes, SoundCloud and YouTube. The Big Questions is part of the Sun-Times Media Podcast Network.On Sinatra’s nocturnal habitsFrank Sinatra never went to bed until the sun came up, whether we were on the road or off the road. He was a hang out guy and he was nocturnal. He really didn’t sleep good at night. It might have been from his big band days. He liked you to hang out with him. And it was fun for 8, 10, 12 years. After awhile, that wore out – but I wouldn’t have missed it for the world.There were times that I wished I hadn’t stayed up all night long. But being with Frank Sinatra, I knew it was the end of an era. He was that I was with somebody beyond a living legend. Arguably the greatest career show business has ever known, and I wanted to be a part of that. I knew it wouldn’t last forever.On profanity in comedyAm I a prude? I’m a street guy. I know every dirty joke there ever was. I can work any stag party with anyone. I know how to write dirty material. But the problem with the F-word is: it’s a noun, it’s a pronoun, it’s an adjective. it’s an adverb and anytime you can’t think of anything creative, that’s where you go. Comedy should not be boxed. You should go anywhere your mind wants you to go. You cannot suppress comedy.On the aftermath of the Comedy Store strike and Garry Shandling, who crossed the picket line.I’ve never been back. I won’t go in there and perform. No, I’ve never talked to [Shandling] since. And I don’t care to. I sounds like I’m bitter, but I’m really not. I wish them all well, I really do.On maintaining his friendships with Letterman and LenoI’m a loyal guy, and those guys know that. So when they had their little rivalry, I told Jay and told Dave more than a dozen times: Are you guys crazy? You should appear on Jay’s show and Jay, you should appear on David’s show. The audiences would love it. The networks would go crazy, but you guys are in control of your shows now. Tell them, ‘Look, we started out together.’But there was a bitter rivalry, not from Jay to be honest with you – Jay got the show that he wanted. David was feeling really offended by that, and felt like he was betrayed somewhat, and I couldn’t reason with that. Even though everything always works out for the best. David’s won all the Emmys.On the perfect jokeFirst of all, following the simple rule of writing a joke. There are two simple rules.1) Comedy is 9/10ths surprise – the audience laughs because they didn’t think you were going to say that or do that. So the set-up line has to hide the punch line.2) There are no victimless jokes. Who is the victim in the joke? Someone has to be the victim – is it you? The Government? The airline?The Big Questions is part of the Sun-Times Media Podcast Network.