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Welcome to another episode of the Comedic Pursuits podcast. I’m your host, Seth Payne. This is the show where I sit down with comedians to talk about their beginnings, their processes, coming up in the comedic scene, and their general adventures so far in the comedy world.
I am so stoked to give this episode to you guys. I was able to sit down with someone who, if you’re a fan of stand-up comedy and have been paying attention to it for the last 20 years, you’ve definitely heard of.
I’m talking, of course, about Dane Cook.
Highlights from my interview with Dane Cook
I was first introduced to Dane Cook’s material in high school when he released Harmful if Swallowed, an incredible comedy album. He later came out with Retaliation, Vicious Circle, Rough Around the Edges, and Isolated Incident. He’s been in such movies as Mystery Men, Waiting…, Employee of the Month, Mr. Brooks, Good Luck Chuck, and My Best Friend’s Girl, to name a few. In 2014, he directed, wrote, starred in, and produced his own special, Troublemaker.
We’ll talk about Dane’s beginnings in Boston and moving to New York City and then eventually LA, and it is fascinating. He’s such a charismatic, down-to-earth dude. The stories he tells are hilarious, and it was such an honor to be able to talk to somebody I’ve looked up to for so long.
He’s going to be on tour again for the first time in a while with material he’s been developing for the past three years. It’s kind of a big deal. It’s called the Tell It Like It Is Tour, and it’s launching on February 20, in Huntington, New York. He’ll be in DC on February 23, at 7pm at DAR Constitution Hall. If you haven’t bought your ticket already, you should because this is gonna be one for the books.
I hope you guys enjoy this interview as much as I did. Without further ado, Dane Cook.
Some parts of this interview have been edited for clarity. To hear Dane’s full responses, listen to his podcast episode.
Early influences
I found myself, even at a very early age, watching comedians and studying them. I was more interested if I knew a comedian was performing somewhere on television than in doing my homework. Early, early on in my career, I got ahold of some comedy albums and was listening to everybody, Carlin and Pryor and old Cosby stuff and Newhart.
I loved physical comedy, but at the same time, I really respected storytelling. I would kind of pipe dream about being a comedian someday and wondered if I could be a performer who wrote and improvised on the fly. I wondered if it was possible to have all those elements and incorporate some of the enthusiasm I saw from comedic actors and people like Martin Short. I was watching him on Saturday Night Live when I was about 13 years old, doing Ed Grimley and Jackie Robinson Jr.’s 100,000 Dollar Jackpot Wad characters, crazy stuff. I loved his dedication.
I think I loved anybody that committed across the board, to their routine, to their physicality, to their beliefs. It turned me on. I felt like I might be able to try it, and I thought I might be able to do it. It was an exciting time.
Growing up as an anxious kid
I went to a school called Minuteman Vocational Tech, a school for learning a trade, for high school. My mom and dad wanted me to go there because they knew I hadn’t really mentally committed to what I wanted to do with my future. As a kid, I was also a little bit behind in terms of development because I had a lot of anxiety, and I was an introvert. I couldn’t speak to people. I was a wallflower, to the point where I don’t even know if I was even in the room, let alone the wallflower. I was definitely behind in the development of my social skills.
So I went to this vocational school to do graphic design. I stayed there for a year, and then I told my parents I wanted to switch to Arlington High School because they had a drama department. I switched, and it all worked out great. I got into drama and did a lot of plays. But the year I spent at Minuteman, I spent learning what would ultimately be the first version of Photoshop before it was Adobe, whatever the first version of computer design was. That helped me down the line in an unprecedented way because, not only could I make my own fliers for local gigs, but I could also design web pages. I knew how to make things fancy.
When I talk to young comics, I tell them everything is part of the recipe. Everything you’ve done, whether it’s, ” Oh man, I didn’t start until I was 30,” or, “I grew up in an abusive household that made it hard to concentrate on comedy,” anything, those are the things that are going to build your character and characteristics. If you can get all the fundamentals, if you can start getting some interest because you’re doing something dynamic, if you can get those little kernels, all that other stuff, when it all meets, it becomes your persona.
I believe that, for me, all those early introvert moments were observational moments where I was watching behaviors and absorbing what I wanted to be. I wanted to be outgoing. I wanted to be like some of these other kids. So I was watching them enjoy their time at recess or in the hallways. I was kind of a like a probe droid in Star Wars. I was absorbing all this information so that I could, years later, use it as a way to explain what I thought made us tick. So it was humble beginnings, but I’m glad I went through what I had to, to utilize it later.
Getting into all forms of comedy
When I first started doing stand-up, I just wanted to be a stand-up. I wasn’t interested so much in doing sketch. I wanted a mic in my hand, and I wanted that feeling of being at the helm and taking a crowd on a journey. That’s kind of how I picture myself.
I graduated high school with a kid named Al Del Bene, who’s still one of my best friends today. We met when we were 14 and went through junior high and high school together. In high school, I said to him one day, “What do you want to do after school?” And he thought of a couple of things. But I said, “I want to be on Saturday Night Live.” And he goes, “I want to be on Saturday Night Live.” I go, “No, I’m serious.” He goes, “Oh, I never miss it.” And all of a sudden, we were talking about SNL, and we were both invigorated by this idea that the two of us wanted to be performers.
So what did we do? We graduated. We started going to Catch a Rising Star in Cambridge, Massachusetts. We started doing open mics.
Al went to college, and I didn’t. He went to Bunker Hill Community College. We’d been dabbling in stand-up, doing open mics wherever we could get up. And he called me and said, “Hey, there’s an improv and sketch comedy group here at Bunker Hill, and we need another member.” So I ended up joining they’re sketch comedy group.
I was with these guys for four years. I was still doing my stand-up independently but also doing the group thing and learning how to be collaborative, how to write for somebody else, how to just go off the cuff. We were putting all these elements together that really weren’t part of traditional stand-up.
I was also playing guitar on stage. I’d written funny songs. So I was using all these moments to sharpen tools, which would then later absolutely inform my stand-up, probably more than people even realize. Because if we were to spend another hour and just talk about the albums or specials, you’d probably be floored if I told you how much of it I’d made up on the spot. I don’t think you’d believe me, and I don’t talk about it a lot because I don’t think people would truly believe that I went in front of 20,000 people and free-formed for 20 minutes. But I did.
The Boston comedy scene in the ’80s
I came up surrounded by the best of the best. Because the comedy boom of the ’80s, as you probably know, in Boston, New York, and Los Angeles, was on fire. I think we counted once, and there were 45 simultaneous shows going on within a mile radius in Boston. Somewhere, there was a packed comedy club or the attic of a Chinese food restaurant, some pizza place with a back room. Everybody had a spot, and a lot of them were incredible, really giant spaces filled with people that were getting on this comedy bandwagon that started in the ’70s and then exploded in the ’80s.
When I came up, I was watching all these men and women who had been doing comedy for so many years. They’d had their success. A lot of them went to Hollywood to look for a little bit of of a breakthrough moment. If they didn’t find it, these masters of comedy came back, and those were the guys who were still working the Boston circuit when I started.
When I started, I was doing all these shows, and all I was trying to do was be confident, more than even putting together five minutes of funny stuff. I was still looking for my voice and a level of comfort on and off stage, but primarily on stage. Because I knew people could read fear. I knew people could read body language. I knew there was a lot of stuff I had to wring out of the towel before I could just stand there and say some things that I thought were funny. It was a process.
But my energy and physicality onstage was always organic. It was never false energy. It was never a put-on. I never thought I needed to be more physical. It was an exuberance that was truly coming out of me because I was finding confidence, I was finding life, I was finding participation, I was finding chemistry with people, and camaraderie.
All those things were equaling a bravado onstage because I was pumped. I was just so happy, and it felt like, for me in those early formative years, “Hey, you know what? This may not be polished, well-crafted wordsmith material, but it’s real. It’s real. I’m really feeling what I’m feeling, and I’m really putting on this performance coming from a place of truth.” And that was more appealing to me even than being the funniest guy.
So I went with it. I didn’t mind being known as a physical comic at the time. It wasn’t until years later that I wanted to break the mold on it and challenge myself as a comedian to expand.
Success and failure in Boston
Near the end of my time with my comedy group in Boston, we got invited to perform at the Boston Garden as part of the Rock of Boston event. I think it was 15,000 people, and me and all my buddies went up on the stage. It was bad. They put us on three hours into the show. We weren’t opening it. We were after the Spin Doctors and right before Phish. People threw lighters at us, and people threw their shoes at us, and we got booed off the stage. It was mortifying.
It was the first time I ever felt humiliated as a performer. People would say it was out of our control, and they didn’t set us up right. But it still felt how it felt. I remember after that feeling like I was never doing a show again unless I really felt like I had an understanding of what I was stepping into. It was a good lesson learned. And then it was then nice to go back to the Boston Garden again and play there for Vicious Circle, in this place where I’d bombed in front of my entire city. It was a bit of a redemption moment.
Making the move to New York
In Boston, I was living with a girl. I’d come home from a gig a day early, and I walked in, and she was cheating on me. She had a guy in the basement, and I could hear the throes of passion as I was chugging orange juice out of the carton. I put the juice back and went to the door and listened. I turned around. I quietly got all my stuff together. I walked out the door. I never confronted her, nothing.
I got into my car and went to a payphone and called my friend, Matt Frost, who was an assistant to a management company in New York. Funny enough, he’s my tour manager today. We book everything together, and we’ve worked together since we were kids. I said, “My girlfriend just cheated on me. I have nowhere to go. I’m coming to New York City, and I’m going to pursue my career there.”
I drove straight to New York and crashed on his couch for a little bit. I went down to Caroline’s Comedy Club on Broadway with the goal of doing a five-minute set. On Monday nights, you could give them $35 and get a TV-quality tape, and I didn’t have one to present to people for auditions. Very long story short, I was approached by a woman from ABC and another person from MTV after my first set in New York City. They both gave me cards and said, “Hey, something’s going on here. Talk to us.”
I didn’t have a manager, so I met with one and said I’d just gotten this interest from these people. We met a couple more times, and I decided to sign with him, but he said I had to come to New York. I was like, “Shit. Okay. I’ve gotta make this permanent.” And before I even had time to be afraid, I was already living in New York.
The San Francisco Comedy Contest
In 1998, I flew out from New York to do the San Francisco Comedy Contest. I was in the top five with Mitch Hedberg and Doug Stanhope. I’ll never forget it. Never having done the West Coast and coming up with these guys, and seeing them… We’re obviously three very, very different styles of comedy—three different styles of people—and yet, we worked well together. The people who put on the festival liked that we were going all the way to the end with it because it was a well-rounded show. You had a little of everything if you had the three of us out there slinging jokes.
I was in San Fran with the idea of coming back to New York. I had no desire, at that point, to go to LA. I wanted to really continue to hone what I was working on in New York. But what happened in San Francisco was kind of similar to my first night in New York.
A producer, Michael Jacobs, came up to me after the set in San Fran and said he thought I’d be great for this part in a show he was shooting. I’d never done television. I’d never been on a TV set. He said the part was playing Betty White’s grandson and Marie Osmond’s son.
Betty White is one of my comedy heroes. Her whole career, everything she had done, I knew her ability was astronomical. So even though I didn’t know if I would be the right fit to do a show with Marie Osmond, considering my comedy was vulgar and rash and lewd and all the fun stuff, I said to myself, “I can’t not do the show with Betty White.”
So I went to LA and ended up doing a full season on this TV show, shooting it at ABC Disney. That was awesome, driving onto a movie lot every day, literally giggling in my car being like, “I can’t believe this is my life.”
The show was called Maybe This Time. I like to jokingly say, “Maybe not.” It was canceled after the first season. Nobody saw it. It was on Saturday nights at 8:30. My own family was like, “Yeah, we’re not gonna be able to watch that. We’re gonna be out.”
Getting a break at The Laugh Factory in LA
I was learning from Betty and everyone on the show. And I was performing my stand-up in LA, while I was living at the Hilton Hotel or Holiday Inn down the street. Something happened there, too, which, again, felt organic.
I was performing at The Laugh Factory in LA. Someone introduced me to the owner of the club, and he said he could put me on stage. So I went up on a Friday night. I think Harland Williams was on the show with a couple other heavy hitters. So I went on after these great, great comics. But when I came off, the manager said, “That was incredible. This is your home. If you want to come here any night, I want you to come here.” Nobody had ever offered that to me before.
I stayed through the season working on the TV show, 13 episodes, and every night, I would perform at this place. This was still 1998, and by the end of the season, I realized I was the only East Coast comic with an East Coast mentality and attitude and swagger that was young out in LA. There were a lot of iconic people, but there wasn’t anybody representing the college crowd or the next generation in LA.
I realized I could go back to New York and fight for stage time and be one of a bunch of those kinds of guys—many of whom, by the way, are thriving today as very successful comedians—or I could stay in LA, be more unique, and build up a unique persona to ride me through, hopefully, a bunch of years doing stand-up comedy.
So it was fortuitous that I did the San Fran thing and did the TV show. It kept me in LA. For the first many years here, I told myself I was probably going to end up back in New York, year after year. Finally, I just found myself loving it out here and wanting to be based out here and put down roots. Maybe even a little part of me felt like I could leave that scared kid in Boston behind and be this new thing out here. I’m sure a lot of that was what predicated it. But I’m still here.
Harmful If Swallowed
That first album, Harmful If Swallowed, was everything I’d worked on for 10 years. So talk about having it polished and ready to go…
I’d done a gig at The Laugh Stop in Houston, and they had a DAT recorder, which was the high-tech system for recording at the time. I did seven shows, got some DATs, and took all the recordings back to LA. A friend of mine who was an open mic-er at the Laugh Factory worked at Premier Radio cutting radio ads. I told him I had a bunch of DATs and asked if there was any way I could transfer them onto the computer just to hear them. He said he could actually splice them together and edit them with me. We had to sneak in there on weekends because we weren’t allowed to be in there working.
I listened to all the material in the first weekend, and I was impressed and distraught. I was impressed because it sounded amazing. It sounded like a comedy album. I was distraught because I used to swear so much more, and there were F-bombs everywhere, to a point where I learned a lesson listening to myself. I needed to learn more language. I needed to be able to use 10-point words and two-point words. I think we counted 48 F-bombs in an hour. There were places where I was just saying “fuckin'” all the time. We went in and surgically spliced, spliced, spliced, and I think we left eight of them in.
So we took the best pieces from all seven shows and put it together. And what I found was, it was seamless. Laughter is easier to edit to because it’s so bizarre. There’s no template for how we laugh, so you can cut anything, anywhere, and just hear one person laughing in the background from another take. Everything fits as long as you’re pausing and taking a breath.
On the last day of editing, I was in the restroom and right in front of me was a bottle of solvent or some kind of cleaner, and it said on the back, “Harmful if swallowed.” And I walked out with a double entendre kind of title. I had that and “brace for impact,” and days before, I decided to go with “Harmful If Swallowed.”
Getting into movies
I guess the theme is, things just came to me from working hard where I was standing. People started coming to the club who were emerging directors, some of them very well-known. Kevin Costner was coming down to my shows, and he’d won an Oscar for Dances with Wolves. People were starting to support me who were successful in their own right and didn’t want or need anything from me. They were just enjoying my passion, my performance. I started getting calls from these writers and producers.
As I started to meet people, from time to time they’d give me a buzz and ask if I wanted to be part of their projects. As I started going down the road of acting in a more serious way, I found I had the exact same drive and need to learn more about writing and producing movies. I had this insatiable need to really understand all sides of it. Because I grew up loving Jerry Lewis, and Jerry Lewis wrote, produced, directed himself, created technology to film himself. I loved that you could be a pioneer in some ways in this industry and try to come up with newer and possibly better ways to expedite something.
So I was on movie sets suddenly, and some of them were independent or bit parts. But every time I left that set, I realized the work was important to me. Collaborating with a group of people away from stand-up felt like my early sketch days where it wasn’t about me. I didn’t have to be at the center and keep all the plates spinning, as stand-up dictates. I could be a piece of a puzzle for a director’s vision or the story he or she was trying to tell, and I could be utilized. I was fortunate enough—and have been fortunate enough—to play in both sandboxes.
Hosting SNL
If I go back on my whole career and have a “holy shit” aha moment, it was hosting Saturday Night Live in 2005. That was, for me, maybe the moment of validation beyond anything.
I was asked to audition for SNL while I was still in New York, after Adam Sandler left. Before the audition, I sat on a bench outside Rockefeller Plaza and had an anxiety attack. I was sitting there, my throat closed, my hands clenched. I started to cry because I knew I couldn’t do it. I knew I wasn’t ready. I knew I was not prepared for the social relations with people behind the scenes on a comedy show that I respected. I knew I couldn’t fight for myself because my spine wasn’t really built at that time. So I didn’t do it.
I passed, and I watched Jimmy Fallon get it and be very successful and great at it. There were lean years after that where I wondered if I’d messed up or ruined an opportunity. I was having some regrets and second thoughts. But still, I felt like it was meant to be, and it was going to work.
When Harmful came out in 2003, I told Lorne Michaels I wanted to come back and host and that it’d be a dream come true. He said to me, flat out, “You’re not gonna host.” When I asked why, he said SNL was doing more mainstream people, people who were in a movie or promoting. I said, “I know, but you used to have Carlin and Pryor and Steve Martin do it.” And he said that time was over.
Retaliation came out in 2005, made the Billboard charts at number four, and was the highest-charting comedy album in 30 years, since Steve Martin. I was in Vegas doing the Vegas Comedy Festival, and my phone rang. I picked up, and it was Lorne Michaels. He goes, “You’re hosting.”
I found myself standing backstage in the dark back area behind the door, hearing the band, remembering what it felt like to be in high school, standing behind the set of Grease or Anything Goes. I had that feeling of, “Okay, I’m gonna walk out the door and do my intro moment.”
I remember as a kid, when I was 12, staring at the door, waiting for whoever the host was to come through and always wondering what was behind the door. And then suddenly, I was standing there, just me and a producer. It’s just a lot of lumber and wood. There’s nothing back there. It’s just a little, tiny cramped spot. And I remember thinking, “What’s back there? What’s behind that door? I am.” And I walked out and, boom, did my shtick.
Isolated Incident
This upcoming tour is newer and part of what I think is a continuing evolution in my comedy. When I was in my twenties, I wanted to be a comic that catered to the college generation. When I was in my thirties, I wanted to become more prolific in my ability to speak and paint verbal pictures with words and phrases. As I went through my thirties, unfortunately, there was a lot of hardship. My parents both got sick. I put my brother in jail for this terrible theft I experienced with him. Then I went through all that stuff with Louis CK.
I was on the receiving end of lies and people just wanting to take me down pegs, quite simply because I got there, because I hit this plateau. I wasn’t even really able to fight it because you can’t fight lies. If you fight a lie, you’re going to start seeming like you’re trying to hide a truth. So for a while, that informed my standup.
When Isolated Incident came out in 2009, I’d come through all this hardship, and my stand-up at that point became dark. It definitely didn’t have as much of the joy in it or the silliness or whimsy. It was caustic and sharper, and I was talking about haters and the backlash and cancer. But I was also talking about the truth.
Troublemaker
I went through that period, and by the time I got to Troublemaker, which I directed and released in 2014, I started to feel the old-school observational quirkiness coming back. But now it was landing with introspective behavior. Once I felt that was happening, I put Troublemaker together. I felt like—and I do feel like—it was my best work to date.
I felt like it was funny in its material, but also funny in all the realms. There’s improv, spontaneity, heckling, just so many aspects of what I failed at many times coming up that I finally had some power over and was able to put out.
Then I decided to go back to LA and not do anything for three fucking years. I wanted to be an open mic-er again. I just wanted to be a fresh face in some ways.
The Tell It Like It Is Tour
I made it, and a lot of good comes with success. A lot of weird, unexpected elements come with success. What do you do? You go right back to leaning into who you are, what your beliefs are, what your constitution is. And I did that. I started working the material. When I toured underground last year, I was getting feedback from people unequivocally people me this was the best work I’ve ever done.
I wouldn’t change all that shit that got slung at me and the spanking machine I went through. I don’t care. Fair, unfair, that’s for other people to discuss. For me, it solidified where I was as a performer. I’m 29 years in now. So the material lands, finally, after all these years, in a place that is the two things I wanted to be throughout: observational and introspective.
Why did it take three years? Because I wanted to do it in a way that didn’t lose any of the LPMs (laughs per minute). I didn’t want to become a one-man-show version of myself. It’s real deal, love of the game shit. I still have the enthusiasm, the energy. I’m 46, so I might not be able to throw myself across the stage like I used to. But now, I can let my eyes tell the story, stand and deliver without accentuating. I can do both.
So what you have now on the Tell It Like It Is Tour, and why I call it the Tell It Like It Is Tour, is because I’m doing what I’ve always done but now at the highest pedigree, just from the experience, the 10,000 hours that I put in and got back out. It’s a gift to me and a gift I give to my fans—new fans and old fans—who love purist stand-up comedy.
If you want to see a show, it’s great to see something that’s new and remarkable and somebody who’s a new voice and the next thing. It’s important. And yet, nothing tops a seasoned performer who has every possible avenue to go down to make sure you get more bang for your buck, your hard-earned dollar. If someone comes in, sits in a room, gets a valet, gets a babysitter, and spends an evening with you as a performer, you better give them a great goddamn show. And that’s what I’m doing. That’s what this tour is, and I know it’s going to be a high watermark in my career.
I’m not putting on an act. I’m not trying to be something I’m not. I’m leaning in, seeing where it takes me. Whatever happens, I’ve had an amazing career. You can’t take me out of the history books. I did it. I did everything that kid wanted to do when he was pipe dreaming. So now, I’m off the clock.
Advice for aspiring comedians
I really try to relate to comedians coming up and tell them to just go with it. Go with it, lean into it, let it take you where you don’t want to go. Let it keep you where you don’t want to be. Because ultimately, it’s the uncomfortable, low moments in life that inform what gets you back up. Unfortunately, life is more hardship. It’s hard. It’s tough. There’s a lot in our brains that prevents us from just being happy-go-lucky all the time.
We’re just not wired to be a pleasant species all the time. So lean into it. Be uncomfortable. Do the work. Watch the people you need to watch. Listen to people. Don’t accept all the advice, but maybe implement a bit of it. And I think when you do it like that, you’ll find yourself in an unexpected place that you’re meant to be.
Where can people find out more about your tour?
The Tell it Like It Is tour launches on February 20, in Huntington, New York, and I’ll be coming through to the DAR Constitution Hall in DC on February 23, 7 pm. If anybody wants any other information, my website has the entire tour schedule. We’re adding dates and all that good stuff. So I hope that people will come out and have a great time.
Thanks for tuning in
Come back next week for DC improviser and performer Alan Prunier’s comedy story.
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