What Has Comedian Dane Cook Been Up To Lately?

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Comedian Dane Cook doesn’t care if you think he’s funny. He doesn’t even care if you heckle him. After all, the thick-skinned Arlington native has been through his share of trials and tribulations over the course of his career, including a period in the late aughts when he caught his half-brother and sister-in-law embezzling money from him. Now, the entertainer is back in a big way—he’s launching his Fresh New Flavor tour at the end of this month, is producing and starring in a new movie, Guys Night, and is currently working on a documentary about his family drama. We recently caught up with him to talk about Boston comics, cancel culture, and the eternal power of a fart joke.

Why do you think so many great comedians are from Boston?

It’s funny, because growing up in Boston, I felt like everybody was a comedian, regardless of whether they actually had a mike in their hand. The ball-busting was porch by porch, summer night by summer night. It’s the environment and the fandom throughout our years of harrowing sports debacles. It hardened everybody. At least where I grew up, everybody was trying to one-up each other and bust chops. The big joke was going into a friend’s house, and there were six table settings and, like, nine kids. What’s the pecking order? Who’s Mom’s favorite?

How has your comedy changed over the years?

Well, anytime it starts to change, I go back to Boston and fix it to get right back to exactly what I’m supposed to be doing in the first place. I’m a cutup. I’m supposed to say the thing that’s wrong. I have to remind myself of that. I landed back in Boston last year to end my Perfectly Shattered tour at the Wilbur, and I was watching the news an hour before my show. There was a brawl at the Kowloon, and I opened with that for about 15 minutes. I don’t know if I’ve ever been funnier than talking about what I think a brawl at the Kowloon looked and sounded like. It brings me right back to what I think standup is at its core: reactionary and a little bit too much, a little over the top, a little unnecessary.

How do you navigate the current climate where comics get canceled for saying anything remotely offensive?

I don’t pay attention, and I don’t care. When Dave Chappelle spoke his mind on his Netflix special or Shane Gillis got canned from SNL, they made a comeback. The Tom Brady roast, I’ve never laughed so much in my life. I kept saying, “I can’t believe this is live. Comedy is back right now. Right now.” And they’ll never take it away from us again, because enough comics have gone through the wringer of people dissecting their bits. Judging an excerpt of a comedy routine is like trying to defend somebody for a crime, but you’re only allowed to use a tenth of the evidence. With an excerpt, it’s impossible to know where somebody’s heart and soul is. There will still be comedians who misstep, but as far as silencing or tampering with the freedom of speech of comics, that’s over.

So how do you decide if something’s inappropriate?

What I personally did is, a few years ago, I said, “If it hasn’t happened to me, if it isn’t how I see the world, I ain’t sayin’ it. But if it happened to me, and I experienced it, I’m saying it.” That’s my truth. As a comic, I believe that if you’re observing and reporting on things that are actually happening, just like in journalism, it’s fair game. I didn’t write the story, but I’m telling you what happened.

Do you believe the old saying, “Time plus tragedy equals comedy?”

Absolutely. I’m doing a documentary right now, talking about putting my brother in prison during what was the most harrowing time of my life and career. It was the height of my comedy career and the depth of personal tragedy and betrayal. And in the documentary, not only am I laughing at some of the things I went through, but I’m enjoying being entertaining, telling people how I got clobbered, literally eviscerated, by that betrayal.

Does comedy come from a place of anger or pain?

No, I’ve never subscribed to that. There’s certainly something to be said for overcoming trauma and overcoming challenges. You know, a lot of good comedy has come from being bullied or minimalized. But I think it’s really more about understanding people and interpreting those clunky, human moments that we all experience.

When was the last time you snorted from laughing too hard?

Probably just lying in bed with my wife. We’re both scrolling TikTok, showing each other things, and it’s still the funniest thing in the book when the guy comes out on his front porch, and he doesn’t know the whole porch is black ice. He just takes a header and ends up halfway down the driveway. I’m a sucker for slapstick. I was also listening to some old Patrice O’Neal bits, and I laughed out loud, and on the same day, some old Opie and Anthony clips of them playing the Mel Gibson tapes where he’s yelling at his wife, and it was all just so twisted and demented. I had a good long day of laughing at all that content.

Any thoughts on shows like Hacks or The Marvelous Mrs. Maisel, where they show how the standup sausage is made?

I think Hacks is wonderful. I had the real privilege of sharing the stage a couple of times with Hannah Einbinder. She was like, “I’m such a huge fan,” and that made me feel great. I forget that I’ve been around for a minute, but we had this fun back and forth talking each other up. With Maisel, I’m so far behind, but I love it. I grew up loving films like The King of Comedy. Anything that kind of pulled back the curtain of funny people in the world of show business I was infatuated with. In fact, I’m developing something now that’s kind of similar, and I’ve never had so much fun failing miserably trying to get something off the ground.

Here’s my SmartLess podcast question: What’s your process?

Okay, this is my favorite question because I wish you could get me and 10 other comics on a call and say, “How do you write? What do you do?” Because it’s so different. I found out in 1997 that if I wrote something down, when I looked at it again, I’d say, “I am unfunny. I stink.” I realized that when I wrote something down, I hated it and thought it was terrible, but if I went on stage and just tried it on a dead Monday night somewhere, there was hope. If I organically talk about the first thought I have, instead of trying to write 10 things that I don’t even know if they’re funny or not, it’s better.

What’s your technique for dealing with hecklers?

I had a heckler moment a few weeks ago, and she said something about my wife, something about my relationship. And I got really angry. But I learned something in therapy years ago. When someone makes you angry, respond with honesty. So I enjoy that process. Instead of just hammering them, I’m gonna invite them to the table, so to speak. I treat the heckler like, “I know you needed to get something off your chest.” I’ll invite them in, we’ll go back and forth, and at the end of all that, I’ll hit them with some final zinger. But if you’re talking about people who are just disruptive and rude—they’re ruining the show for people around them—I will tattoo them with verbal parries and thrusts. They’ll never outlive it. I get emails from people 10 years later, saying, “We still talk about the night Jonathan got drunk at your show, and you just scarlet-lettered him.”

Photo by Paul Archuleta/Getty Images

Who’s the funniest person you know?

It remains Dave Chappelle. He makes me laugh. I had the luxury of doing TD Garden with him back in October. He asked me to be a surprise guest, and I hadn’t been back on stage at the Garden since I did Vicious Circle. I do my 20 minutes, and I just killed, honestly. Dave is on another frequency, but I turned to my wife and I was like, “No way is Dave going to be better.” But he comes out and my wife and I were wiping tears away. I was giving him a standing ovation mid-set.

Who’s the comedian that you weren’t around for but you’d most like to meet?

Oh, man, George Carlin. At times in my career, when there was a lot of pushback against me and people were not happy to see I was succeeding, he inspired me. I’d remember Carlin doing the Hippy Dippy Weatherman and then the day that he went on television and killed it. He brought the cardboard cutout and threw it out of the frame, and said, “He’s dead. I’m not this guy.” And he literally kind of killed his career, but he allowed himself to say, “I’m changing, and if you don’t like it, I don’t give a rat’s ass.” I would go to the Museum of Television and Radio over in Beverly Hills and dial up that clip. For years, if I was feeling really low, or scared, or ostracized, I’d remind myself that we’re all growing, and we can all change. If I could ever sit at George Carlin’s knee and ask questions, I would revel in that.

What was your worst moment on stage ever?

I was in a comedy group, and we did the Garden in 1992 as part of WBCN’s Rock of Boston show. Phish was the closing act. They put us on not at the beginning of the show but two-plus hours into it, right after the Spin Doctors and before Phish. Being huge Phish fans, the entire crowd threw lighters and sandals. I got a welt on my neck. I got hit so hard with a lighter that I swear to you, if it hit me in the eye, I would have lost my sight. Whenever I describe it, I say, “You ever see the opening of Saving Private Ryan? Yeah, picture that, but with sandals and lighters.”

Do you miss doing film? It’s been a while since you appeared in a feature.

I’m gearing up to do one now. I’m carnivore dieting to get myself down to fighting weight. I’m starting in August. It’s the first movie I’ve done in probably 10 or 12 years. I love comedy. I’m always going to do that, but I love the collaborative process of film. But for the most part, the stuff that I was being sent was either really derivative of what I’d already done or just really watered down, and I was like, “Okay, I could take a million bucks and do this movie, but then my fans are going to be like, ‘Dude, what the fuck is this?’”

Is voice-over work the easiest payday ever?

It’s the most convenient payday, but I wouldn’t say it’s easy. I was working on Planes, and it was especially tricky because I was replacing an actor who had been fired. John Lasseter thought my voice had the boyish whimsy he wanted. The amount of work that went into doing it right and giving those animators what they needed was a lot more work than I thought. So yes, you roll in in your pajamas, and there’s no hair and makeup. But after that first take, you very quickly start to realize that this isn’t just about putting on a cute voice. You gotta land it, and it’s really, really intricate work.

Biggest personal extravagance?

I turned into a bit of a sneaker-head over the past couple of years. Podcasting became so in vogue that I realized you can’t go on a podcast with the same sneakers every time, so I started buying a new pair every time, and I think I probably have about 200 pairs now in my closet.

Are fart jokes inherently funny?

Oh, yeah. Fart jokes work, especially if there’s a sound effect in there. If the line that follows is original, then you’ve got yourself a winner.

Do you have a personal motto?

Breathe and believe.

Photo via OsakaWayne Studios/Getty Images

By the Numbers

We’re Funny!

The Boston area’s biggest export just might be comedians.

13

Number of The White Lotus episodes in which we got to enjoy Norwell native Jennifer Coolidge in her portrayal of Tanya McQuoid.

 2013

Year that comedian Ayo Edebiri—of Big Mouth and The Bear fame—graduated from Boston Latin School, where she was a member of the Yellow Submarine Improv Troupe.

11

Number of standup specials Canton native Bill Burr has released.

2

Number of times Brookline’s own Conan O’Brien served as president of the Harvard Lampoon before becoming an SNL writer and going on to fame as a late-night television host.

4

Number of comedians—Steve Carell, John Krasinski, Mindy Kaling, and B.J. Novak—who starred in The Office and hail from the Boston area.

First published in the print edition of the August 2024 issue with the headline, “The new Dane Cook.”