The 1980s—when most millennials are said to be born—is commonly referred to as ‘the comedy boom.’ Following that era was ‘the bust’ of the 1990s when many comedy clubs nationwide shut down and big money gigs began to dry up. With the rise of the internet and Comedy Central at the turn of the century, the rumblings of a Comedy Boom 2.0 could be felt. One of those indicators was the rising popularity of a young, attractive, internet savvy stand-up out of Boston: Dane Cook.
I’ve always been a fan of the energetic stand-up since grade school when I discovered his bits on Napster—which I’d later learn he uploaded to the pirating site himself. I was at the HBO taping of his Vicious Circle tour and was one of his millions of Myspace ‘friends.’ Fellow comics teased him for his use of what would be called social media and other comedians mocked him for his athletic act outs. Despite all of that, the self-promotional tactics and fan engagement worked. By 2004, he had the most successful comedy album release since Steve Martin in 1978. Forbes called him “the first internet-made stand-up comedy star.” And TIME named him one of the 100 most influential people in 2006.
Cook made comedy cool again at just the right time, going viral before going viral was a thing.
When I started doing stand-up 10 years ago, I was shocked to learn that a prerequisite to being a comedian was hating Dane Cook. For some reason,
people comics just did not like him. For some, it was his energy. For others, it was potential impropriety around a few jokes. Some comics find him abrasive. Though the conversation of what’s funny is always open to debate, the laughter of thousands of people show after show cannot be ignored. The insistence of many to shout how unfunny he is seems unfair. Some people don’t think Brad Pitt is a good actor, but there aren’t coalitions of actors telling anyone who will listen that Pitt’s massive success is unwarranted.
The Good Luck Chuck star insists there is no chip on his shoulder and says journalists bring it up more often than he does. But if he were to have resentment towards the comedy community for trying to drag him down as his rocket rose, that would be understandable. There is a lot to be proud of in his nearly 30-year career as new projects seem to have the man energized as he creeps into middle age. Many have held grudges for far less.
I sat down with the very charismatic arena-filler hours before his show at The Met opera house in Philadelphia for his Tell It Like It Is tour. It’s Cook’s first domestic tour since 2013. His last special, Troublemaker, quietly came out the following year on Showtime, though you wouldn’t be able to watch it now on any official platform.
We discussed his evolution on stage and off, the power of transparency, and what happened (and might happen) to his ‘lost hour’ of material.
This interview has been condensed and edited for clarity.
The Dane Cook interview
Dane Cook: I feel like every time I’ve chatted with you guys, it’s been on the cusp of interesting times. A lot has changed. Some things haven’t and some things have really progressed.
Laughspin: So what hasn’t changed?
Somebody wrote me today on DM who said they’d been to some of my other tours in the past. They said, “I saw you last night in New Jersey and it’s my favorite of the three shows. You’ve still got the antics, the energy, but now you have a new kind of introspection.” And that’s what I always wanted to get to in my comedy. Stuff that guys like Chappelle and Patrice [O’Neal] were doing really early, which was not just observational how they see things, but how they feel in conjunction to those things happening.
But in the last 10 years, it started to become much more personal. Then in the last three years preparing for this tour, a lot had changed in terms of what I had wanted to get to in 29 years [doing stand-up], what I finally accomplished that took me a lot longer than some of those guys that I mentioned. I always wanted to be a certain pedigree. A certain pedigree was important to me.
Of comic. And seasoned. Two words that I felt like I was ahead of, to be honest. I broke; I made it; but I still knew I was learning. I’m doing arenas, but I’m thinking, 15, 20 years in, “I’m still kind of a baby.” People say, “You were at the helm of—,” yea, but I was also starting to look at comedy very differently as I was evolving and realizing I want to continue to grow up with this audience that I discovered when they were in college. If I’m more introspective, I can reach newer fans that were behind those people. And hopefully those [new] people will be on the ride for the long haul.
So it was everything kind of smashed into one, like three or four years ago. It took me a little longer before this tour because what I didn’t want to lose was the LPMs—the laughs per minute. I wanted to be able to tell stories, but not in a one-man show style—not in a downshift. I wanted to still tell things that were stark and caustic and interesting about things that have happened to me in my life without giving up the level that I have come to expect—and my fans have come to expect—of laughs in there.
So it took a little bit longer because I was turning a corner in my life as a comedian. 29 years in now, it was like all starting to congeal.
I started seeing that turn at ISolated INcident as you got a lot more personal. You were in a more intimate setting instead of the massive arenas.
For me, a lot had happened in and around that time. Obviously, my parents and my brother and everything was shifting. When I filmed that special, I remember feeling this might be a quick downshift for my fans who saw me coming off 10 years of being bombastic.
Fewer kicks in ISolated INcident.
Fewer kicks today! I’m 47, man. I’m not going to be doing any dropkicks.
I’m deeply proud of that special. Every once in a while, my own clips will come up in a Spotify or shuffle. When I hear routines from that moment, I’m like, “Oh wow.” I dug in. I was doing that thing about the hater—the @anonymous.com—that fucked up letter that I got. I was listening to it a few years ago when it popped up and was like, I was ahead of myself.
I did want to be more introspective and talk about the animosity towards me or even the successes. I wanted to be able to do it without being braggadocious but still take the piss out of myself. How can I do both? How can I brag a little about what I’ve done—because what I’ve done is fucking amazing and very rare—but also a lot comes with it that’s pretty brutal and baggage in isolation. So in that special, I was starting to spin those plates. But I think, in some ways, my fans weren’t at that point quite ready for that. So the reaction was definitely varied. I had people who didn’t like it that have now watched me and say, “I hear bits on Isolated now that I really love.” I don’t think they were looking for that introspection 10 years ago or whenever that was.
Whether you’re five, 10, or 20 years in, a lot of comics look back at old material and cringe. But you are in a unique situation because you’ve had to so staunchly defend almost all of your material—either because of the joke stealing allegations or people going, “Those aren’t jokes; they’re sound effects!” or just general hate. Whatever the attack, you’ve spent so much emotional energy defending it all. So now, what do you think when you look back at your old stuff?
I had to look at a lot of stuff for a documentary that I’ve been putting together with a buddy of mine. The first thing that I cringed at more than anything was just the look: the styles and the hair. I’m finally at that place in my life where I’m looking back going, “Why did I wear that?” Or I’m wearing this oversized leather jacket. I loved guys that were larger-than-life in terms of their stand-up like Eddie Murphy, so I felt uncool in my life.
I wasn’t a cool kid. I wasn’t popular. I was the quiet kid in school. So this character, so to speak, was the guy I wanted to be. But I didn’t feel, for me, that I was the hot comic. I thought, “I’m ‘the now comic.’” I’m speaking to a generation right now that knows the lingo and knows how to relate to me on it.
It’s interesting to look back, but everything we’ve been talking about has been, “Here’s a piece of the puzzle I learned over here,” and I learned how to promote myself over here, and how to become a business person over here, and then funnier…I just wanted to have more tools to be able to tell more stories, to be able to make people laugh for an hour and a half and being able to hit every button. And also to be able to do it in a real organic way that doesn’t just feel like a routine. If you watch me five nights in a row, it’s going to be different.
It’s the most present that I’ve ever felt. I can explain it simply like this: When I was back breaking through, I was thinking of the future constantly. “I got to get there. I got to do Saturday Night Live. I got to do Madison Square Garden.” So I was always racing towards something and really not reveling in what was happening at the moment. And then I had all the things with my family and my brother and Louis [C.K.] and all that stuff. So it was a lot of hindsight looking back at my life and trying to figure out why. I wasn’t being healthy to myself. I was beating myself up. I still had low self-esteem even though I was this big important—quote, unquote—comedian.
The last five or six years, when I’m on stage, I’m so present. I’m in the room. I’m not thinking about the next—I’m just thinking about right now, this show. Now I have the tools and I’m not searching for something else.
I’m still trying to learn. I watched Carlin shift so many times in his career. But the thing I loved the most about Carlin is, for as many times as he maneuvered—and he really changed and he really challenged his fans—the LPMs were always there. He was always silly.
Of course, I had a lot of mentors [like] Buddy Hackett and Jerry Lewis and guys that I knew—Rodney [Dangerfield] I used to host for back in LA when I first got there—so I [realized], “Wow. The key to longevity is to be so knowledgable about who you are—your flaws and your strengths—when you share those with people, you’re more transparent. When you’re more transparent, more people are interested. And not in the flotsam and jetsam of, “Did he do this?” or “I used to not like him, so should I like him now?” It’s like, all that stuff goes away when people are sitting in the room and seeing you as a person who is wide open as opposed to like, “I’m going to fight to make you love me and you’re not going to really see where I’m in pain.” Now I’m coming out literally like this [Dane extends his arms wide open.]
But do you still care if people like you?
No, no. My point of action when I wake up every single day is to entertain myself, to build my brand up in a way that I’m proud of. So I always want to keep the integrity. For that, you can’t look outward to what you’re doing wrong in some people’s eyes. It’s an impossible puzzle. I probably have thought about that in years past. I didn’t expect animosity in comedy. I never dreamed in my wildest dreams—as a person who just wanted to bring laughter and lightness—that there would be any kind of backlash. It was impossible. When that started to happen, it was almost like, “Is this a joke on me?” I didn’t understand it.
I could understand generationally why some people were like, “Oh, the next cool thing? Now we have to hate that. It’s just because he’s popular.” I do the same thing. I was like that, too. I focus very, very little on people who are not on my ride because what I’ve learned is some people just aren’t on your ride. I DM with people every day. I talk to my fans like in the MySpace days.
You still do?
I still do. Even today. [He pulls out his phone and scrolls through a seemingly endless list of surprisingly current Instagram conversations.] I respond to young comics looking for advice. I send people voice texts. I’m like in constant connection with people. To be able to get on there on the daily and read from somebody who has nothing to lose say, “I didn’t like you. I wasn’t a fan. I jumped on the Hate Dane bandwagon. I got to tell you: I saw your show. Fucking love you, man. Thanks for sticking in there.”
I get a lot of people who tell me they heard me on Theo Von’s podcast or Bert Kreischer. People have never seen this side of me. It’s always been about just the funny element of it. We’re in a totally different time now in comedy and society. People want more transparency in all of their entertainers. That’s happening as I’m happening to do that.
People want to like you, not just the act. People go, “I can’t like that show if I don’t like them when they’re off that show.”
People are also more open to the idea that a comedian doesn’t have to be on all the time. I’m literally doing these podcasts this year realizing, “Oh my god.” This stuff I was doing with my fans on just a one-on-one level on my social media—being really transparent and as honest as I could be—now it’s in vogue. That plays right into where I’m stronger. I can share even more because I can handle the funny over here, but we can have a deep conversation over here. We can get into some nitty gritty and I’m not going to shy away from anything. I think that’s interesting to people.
This current version of you may be less concerned with the haters, but you can’t say you were never concerned with it. I’ve always felt a defensive energy from you in press or on podcasts that seemed to shout, “Why can’t I be at the cool kid table?” It’s always felt like Dane’s got a chip on his shoulder.
I’ve just thought, “He’s Dane-fucking-Cook. Why does he care what other comics think?”
When I’m asked the question, I have to answer it. When I’m in an interview and someone asks me, “What do you think of haters that are outside saying you suck?” well now I’m going to talk about it. But the truth is, I didn’t investigate it. It’s not like I was sitting there doing a deep dive on this.
You weren’t searching for Dane Cook on Twitter or looking for the negativity?
No. I grew up loving certain comics and having conversations with my pals who loved comedy as well—before I even did stand-up—and, you know, this guy hated Cosby and this guy hated Carlin or somebody didn’t like Pryor but they liked Steve Martin. It was like, these were already conversations for me coming up where I was like, “Yea, I don’t subscribe to that.” It took a lot of years before I could finally look at any comic and go, “I may not like that person as a person, but that’s a talented individual. I might not like that person’s routine, but I love them. They’re a great person.”
I think that, as people have come around to the idea of whatever you thought about me or something specific that was white hot at a moment in time, it’s always interesting to take another look at that and go, “Was that me projecting something onto that person? Maybe I didn’t feel valuable? Maybe I didn’t feel like I was achieving my dreams?” And seeing this young punk with nice hair getting his, maybe pissed people off. I can’t answer every angle, but I do know that there was only one perspective that mattered to me outside the conversations like this, and that was: How can I continue to make people laugh? Because I need to focus on them and not the ancillary people on the side.
The easy answer is: We’re spending, of my full year, this conversation will be one of the biggest chunks of time that I would even talk about this.
Again, I bring it up out of a place of concern as a fan. I think you’ve been in my life longer than you haven’t been. Somewhere at my mom’s house is a burned CD of Dane Cook clips from Napster with those intense ‘www dot Dane Cook dot com’ bumpers added to the end—which I didn’t realize you made and uploaded until I was doing some extra research for this interview.
I recorded those in my apartment. I just figured out how to slice [the website name in] and put them up on Napster and Limewire—whatever I could use at that point. It wasn’t about financial gain. It was literally about word-of-mouth and just trying to get my stuff out there. To be honest with you, what people don’t realize is: I wasn’t making it on my own. I wasn’t getting help from the industry in terms of, “Let’s put him on Saturday Night Live.” The momentum that I got in ’96 doing Letterman kind of dissipated. I was doing colleges and I was making some decent money, but it didn’t parlay into anything until I took the reins and was like, “I’m just going to use this internet thing as a billboard.” Then when I saw people could actually chat with me—that’s why I still do it today. It’s very valuable.
I remember years and years ago David Cross giving me shit because he said I was pandering by answering people and talking to people. I remember thinking, “No. If you saw the conversations, I’m not bullshitting [people] going, ‘Hey, everything’s great! Come love me!’” It was literally me going, “Hey, I have rough days, too. Come to my show tonight. Maybe we’ll both feel better.”
You’ve brought up this onstage evolution a lot. What has been your growth offstage?
Aw, man. Incredible. First of all, feeling safe again in terms of—I went through that horrible time with my brother. I thought I had a life savings. I thought I was set. I really did. I thought, you know what? I’ve worked hard for a lot of years. I built my nest egg up. That was gone, essentially. I couldn’t afford a home. I couldn’t afford some of the luxuries I had come to appreciate. It was like somebody hit the reset button and I was back at square one. I was also at square one at a time when I had already come off a huge wave. And a career is going to be all kinds of highs and lows.
As Patrice would say, your first ride on the roller coaster.
Yea. I was coming down the big peak on the first ride, which was still fun. It was a lot of years of going up. So to come down that other side, to have lost security, that almost broke me. That, more than anything that had happened in comedy, that moment almost broke me because I felt like people were rooting for me to lose. At that point, there was a lot of backlash and I was not used to that. I did not anticipate that in comedy. And so, backlash coupled with, “Now I’m broke,” I kind of felt like this might be the end of my ride. It was my darkest time.
Why today is great is because after a while of marinating in that unfortunate sadness that came with it—the betrayal of love from a family member that I trusted—once I got past that, and I started to rebuild, I was now a businessman who was very much at the center of my business. That meant I’m not going to be at a stand-up comedy club every night like I had been for 15 years. I needed to live some more life. I needed to meet people who were away from the comedy circle. So where I’m at now is I’m safe again. I’m in a great place where everything’s flourishing—a new lease, so to speak. When I go home, I’m very comfortable with just relaxing and not just thinking about what’s the next thing I have to do.
You have time for game nights, apparently.
I do have time for game nights. [Cook met his current girlfriend, Kelsi Taylor, at a game night he hosts at his home.] You know what’s actually so funny about that? I started having this game night and it was a lot of Hollywood people coming out.
Did people have to audition to get invited?
No, no. Just friends of friends and basically people that, on a Friday night were like, “Hey, we don’t want to go out and get fucked up and party.” It was people who were maybe also feeling a little bit more introspective in their own lives. So what’s interesting is, for those two years where I took Friday nights off, the relationships with producers and financiers and actors have led to work that were very unexpected because now I’d ingratiated myself with a whole new cast of people that weren’t just comedians in comedy.
See, I want to grow my company and my production business. I’m directing now. I’m writing. I’ve got a feature that I’m going to direct and star in next year. I’ve got another series that I’m going to produce for a Middle Eastern comedian friend of mine who has some amazing stories. Comedy is still my passion—it’s my first love—but I’ve accomplished so much in it that it’s really just the enjoyment of doing shows for my fans. I’ve done it all in that arena. And literally—the arenas.
So now it’s about how can I, for the next phase of my career, tell more stories in new ways. How can I tell more stories in unique ways, behind the camera, just financing something for somebody else—
The book’s been the hardest. I want the book to be—I’ve read a lot of comedy books because I wanted to see how I would approach it. I just want it to be funny as it is transparent and impactful. The first version of my book I wrote a couple of years ago was dark because I’ve had a lot of dark stuff [happen.] I’ve had a lot of things happen even before stand-up that was—I grew up in an alcoholic family. I went through a lot of ordeals, trauma, anxiety, phobias. It’s hard to sit and write all of that as a comedian, identifying myself as a funny person. So I want to have both sides in equal distribution. So it’s been a longer process to write the book because I still want all the humor and the highwater marks in there. What I found was, when I finished the first one, man, this is really the dark side of a comedian’s life.
That’s funny. Just a few days ago, I found these recordings—I always record my sets. I found audio recordings of that full year of the Under Oath tour, which came on the heels of ISolated INcident. But what I had forgotten was, I dumped that material the night I recorded it. The Under Oath tour was a new hour of material. What happened was, I got to the end of that year and I had felt like maybe I was afraid to commit to recording because it was another special that was a little bit more caustic. Now when I listen to it, I’m like, holy shit, I’m going to bring like 45 minutes of this back.
So you’re the only person who’s ever realized that and asked me that. And I think that’s really fascinating and it really shows that you’re on the pulse of what I have done. Because that material I’m going to bring back. Now I’ve got this hour and a half [for Tell It Like It Is,] and then I’ve got that hour—
Maybe another double album?
That’s what I’m looking at. Because it’s very different material. Some of the stuff on the Under Oath tour was really dirty and sexual humor, but then there was stuff that was really about me. Really about not just the comedy I see, but this is what’s happened to me in my life. I’m glad I found those because now I want to bring some of that stuff back and put it in the new material.
Honestly, what an awesome question. I was so enthused to listen to it again and go, “My god, why am I not doing this?” I might even start throwing some of it into the routine this year if I can figure out where it’s going to go.
Another question like that: I was listening to ISolated INcident last night. I was at Rough Around the Edges at Madison Square Garden in 2007 and I wondered, was some of the material from Rough Around The Edges in the ISolated INcident album?
Probably. Everything was so kind of fast-tracked at that time. Here’s what’s funny about Rough Around The Edges: People go, “Wait, when did you work on that material?” Rough Around The Edges was called Rough Around The Edges because I improvised like 60% of the show at Madison Square Garden that night. Here’s what happened. I got the movie Dan In Real Life and I ended up in a production schedule that was much more work in rehearsal time than I anticipated. So I set Madison Square Garden as a show—I couldn’t cancel. And then the two months leading up to it, there was only one club near where we were [shooting] in Rhode Island and that was the Providence Comedy Connection. I got there once to run my hour. I got there one night. My manager came with me. I wrote everything down and said, “I think this is it.” He says, “All right, maybe we shouldn’t record at Madison Square Garden.” I said, “Well, could we do it low budget? Fuck hair. Fuck make-up. Fuck lighting. Can we do it super low budget?” So I rented cameras, essentially. It was not a big film crew. When I got on stage, I just started freeforming within the concepts I had worked on very marginally. So, the Civil War stuff and the flute and—
All that was made up.
I still say that with the people I went with.
A lot of people skiddle-ee-doo me!
That Civil War piece just came from doing a gig in the Berkshires and I saw a picture of Civil War soldiers. They were all doing that stoic thing where nobody smiles. I’m standing in a hallway of this middle-of-nowhere Berkshires hotel thinking, “That’s a bit.” That’s about as far as I had ever worked on the idea of that picture. Then I had gone to high school before I went to Arlington High School at a place called Minuteman Tech. And at Minuteman Tech, there was a cafeteria in it called the Fife and Drum Grill. So I was like, “What’a a fife?” and a guy told me, “It’s a flute.” So these were kernals of things I had seen in my life, and then I got up on stage and—I don’t even know how I seguewayed into it. I just started feeding off the crowd.
So it was Rough Around the Edges because it’s not worked out material.
Also, I looked rough around the edges. I watched the edit and thought, “Oh, this looks like shit. This looks terrible.” I should have done a little make-up and hair because I looked rough. I looked tired from the work on the movie. I was burning the candle at both ends.
What I learned on that night is something I bring to the show now which is: I’m better under pressure. I’m better when it’s not glossy. I’m better when it’s not so riveted tight. I’m better when I do comedy less during the week and have a few things that I really focus on instead of, maybe when I was a younger man, a lot of it is ego. I wasn’t on stage every night learning. Sometimes I was on stage because I wanted to make chicks laugh.
So now when I go into a club, I’m there to work. I don’t put the rivets in. I keep it a little loose. I keep it Johnny Carson. I learned from growing up listening to him in interviews. Stand-up comedy is best served when they know ya, they dig ya, and then you don’t have to feel like you’re selling. I don’t want to feel like I have to sell. I want to feel like I can just hang out and make it a moment.
Tickets for Tell It Like It Is are available at www.DaneCook.com. You can see him in star in American Exit available on DVD, OnDemand, and major digital retailers on May 14.