Dane Cook on the Messy Art of Making a Comedy Special

America’s most/least favorite comic wants to be his own boss.

A lot of ink has been spilled about Dane Cook. Salon has called him “cheatingly smug;” Slate went with “undangerous,” whatever the hell that means. Most of the internet just sticks to “asshole” or “douchebag.” But he doesn’t come across as either hole or bag. He’s just that kid you knew back in middle school who had a little too much energy and little too little restraint – the one your teacher hated. He also comes across as ambitious, which is interesting given that he spent so much of the last decade playing the everyman card. 

But he’s not just another guy. He’s hugely successful and he wants to do more.

When it came time to make his latest special, “Troublemaker,” Cook decided to do more by directing. The guy knows from comedy specials and he wanted to try something new and raw. He’s a bit older now than he once was and he’s just fine with it. Is clever camera work going to make the “superfinger” guy into an elder statesman? Doubtful, but it can help him reframe himself. And, yeah, he takes this shit seriously.

Cook told Maxim about his new process and what he wants to be now that he’s not “that fucking guy” anymore.

What made you want to direct your own special? Was there a specific feeling you wanted to capture?

I’d done a couple of things with Marty Callner, who’s basically the best and he inspired me. The reason I wanted to work with him was the old Carlin specials from the seventies. That look, that feel, the way Mr. George Carlin was captured, I loved that stuff. Then I was looking at the source material for this special and thinking about the way people engage online with YouTube videos that have a more bootleg feeling. People don’t care that the lights glow perfect or that the sound is impeccable. It’s just comedy in its rawest form. It harkens back to the early Pryor sets when he was just sweating and switching out mic.

Not like your old specials.

It’s not a one shot and I’m not in an arena.

What was the actual filming process like?

With albums, you record six or seven shows and, when I was cutting, I would go so far as to use different set ups and punchlines. It’s easy to splice. This special was shot on two nights, on a Friday and Saturday and I got really lucky because the Friday show was a bit of a disaster. There were technical issues. There were people coming in late. It was a busy room so when I hit the stage I knew it would be a rough gig. In my head, I was like, “Fuck it. This isn’t the show.” So I put on a slightly different show. 

I woke up Saturday and realized I’d invested my own money in this thing and that if it didn’t go well that night I was going to have the most expensive home video out there. As a performer, I’ve never approached the stage with that sort of pressure. I was not in the right headspace. But the set was magic.

You basically bailed yourself out.

When I watched Friday later, I could tell that the laughs were less abundant and I was terse, but that actually is me. That caustic attitude comes out of comics. When I mixed the two performances, I felt like it captured something. I was even trying to make it the most funny version. 

That’s an interesting approach. Would you say your goals have changed then?

I’m out of act two of my career so I have to think about what I want to do next. I want to have a different side. I don’t want to be afraid to let that youthful exuberance go.

Do you have a sort of role model for this next part of your life as a performer? Is there someone you look up to?

A person who I’ve gotten to know over the years is Jerry Lewis. I went to see ‘Method to the Madness,’ his documentary, and his daughter Danielle pointed me out and introduced us. I was totally “kerfuffled” or whatever cool word to meet this guy. We exchanged numbers and he started calling me. We forged a friendship. He’s 89 and I’ve learned a lot from him in terms of what he did as he got older, becoming a writer, producer, and director. You know, that’s one of the guys who created the playback monitor. I’m into tech and I really admire that.

Given all that, how do you feel when you look back on the early stuff?

It was a lot more about performance and antics than anything else. There was good material in there, but you remembered me because I destroyed the room. 

I was a performer and a writer. It’s the other way around now.

Photos by Nick Spanos / Showtime