Three Questions with Dane Cook about His 'Absurd' New Showtime Special

by 10:25 AM PDT, October 17, 2014
Photo: Showtime

Dane Cook gambles on himself tonight in his new self-funded Showtime comedy special, Troublemaker, which marks his directorial debut. ET got the scoop from the veteran funnyman (who appeared in Disney hit Planes: Fire and Rescue over the summer) about what to expect.

How do you keep your material fresh in a career that spans over a decade?

“The cool thing about standup comedy is you're always experiencing something in your life that will spark an idea or a concept that you want to take to the stage. In each stage of my life, my career reflected where I was at. My standup in my twenties was indicative of drinking, and drugs, and sex, you know, collegiate kind of things. And then [I was] getting into my thirties and having some more serious life experiences, whether it was losing my parents, or dealing with backlash in an industry that's sometimes unforgiving. I can go and bring those things to the stage and make hay out of things that are pretty heavy duty.”

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What sets Troublemaker apart from other comedy specials?

“A few things, really. This is the first one I've ever directed on my own and I did this completely separate from any corporate partnership. Two years ago I knew that I wanted to direct something, and as I started looking at my new routine, I felt like this might be a great undertaking and a goal that I've had for over 10 years. Lemme see if I can put a team together, which I did, and then the scary part which is, let me write a check. That's always the moment where you start going, ‘I don't know, maybe I don't need to direct this special after all.’ It's always a gamble. [But] my dad used to say, ‘Gamble on yourself.’"

What will surprise your fans about this show?

“I think that the first thing is, it's very light. I went through a pretty tumultuous time about six or seven years ago; both of my parents got cancer and it was very trying on my whole family. And I wanted to be there and spend as much time as I could with both of them. I mean, within nine months they both succumbed to different kinds of cancer. It really hit me hard and there were things that I needed to work on in my own life. At the time I was in the throes of making 'Isolated Incident,' which was the last special I made four years ago, and it was reflective of how I felt. It's monochromatic, and it's dark. The funniest version of morose, I think I nailed.”

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“So [now], I'm feeling great, I'm feeling the best physically, mentally. I've got great mentors and people in my life. And so it feels to me like it felt when I first put out [my 2003 special] Harmful if Swallowed because I just came to it with such fervor, like youthful exuberance. And I went into this special, yes I'm a little bit older and wiser for the wear, but I think that the material is as random and absurd and observationally twisted as I've ever been. So I'm looking forward to people escaping with me for a little bit, and having a good laugh.”

Troublemaker airs Friday night at 10 p.m. ET/PT on Showtime. Watch below to hear Dane's advice on how comedians can spin bad times into new material: