Dane Cook: The Full Story

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Featured: Dane Cook, Bobby Kelly, Jay Davis, Gary Goleman, Steve Martin, Eddie Murphy

What’s in This Episode

• Dane Cook’s rise to commercial success in 2006
• Dane Cook’s pioneering use of the internet and MySpace for comedy
• Dane Cook’s platinum albums Harmful if Swallowed and Retaliation
• Retaliation album chart success and cultural impact
• Dane Cook’s HBO documentary series Tourgasm in 2006
• Comedy industry’s skepticism toward Dane Cook despite mainstream success
• Accusations of joke theft against Dane Cook

Questions Answered in This Episode

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Full Transcript

This transcript was automatically generated and may contain spelling and/or transcription errors.

Caloroga Shark Media. Hey there, I’m Johnny Mac with your Daily Comedy News. On Saturday, we’ve been doing deep dives on single comedians. And today I want you to close your eyes and imagine it’s 2006. You’re in Manhattan.

You’re online outside Madison Square Garden. Someone a few spots ahead of you is playing music off their phone. Your friends behind you are quoting movies back and forth. And 20,000 people just like you are about to pile into Madison Square Garden to watch Dean Cook. Not a rock band, not the Knicks.

Dean Cook. A stand-up comedian who pretty much nobody in the comedy world will admit to respecting. A guy who’s been publicly accused of stealing jokes by one of the most respected writers in the business, if not one of the most respected people. We’ll get to that. Critics have been dismissing Dean Cook as a frat boy with a microphone for two years at that point.

And he was about to sell out Madison Square Garden. Hi, I’m actor-comedian Dane Cook, and I’m hosting the season premiere of SNL with The Killers. The Dane train’s coming to town, and The Killers are in the caboose. Toot toot! In 2006, Dane Cook was the most commercially successful stand-up comedian in America, and almost everyone who mattered in comedy couldn’t stand him for it.

It was this whole weird thing between what the comedy world thought of Dane Cook and what the actual world thought of Dane Cook. Quite excited that our next guest is making his network television debut with us tonight. He can be seen in Boston at the Comedy Connection on October 3rd and 4th. Please welcome the very funny Dane Cook. Dane!

Thank you very much. Yes, I am very, very excited to be here. I’ll tell you a little about myself. When I was a little kid, I was a terrible speller. I could not spell, so my mom and dad tried to help me out.

They got me a little helper, a little friend, a little aid. They got me a little red box called Speak and Spell. You remember Speak and Spell? No, no. They shouldn’t have called it Speak and Spell.

They should have called it Speak Like the Devil. Remember the voice? Hey, I owe you. No, no way. That thing was evil.

That thing used to wake me in the middle of the night. Play with me. Dean Cook grew up in Cambridge, Massachusetts, one of six kids in a Catholic family, and started doing stand-up in Boston in the early 90s before moving to New York and then L.A. Grinding the clubs the way everybody grinds the clubs, doing the thing that takes years to produce anything visible and then mostly produces nothing at all for most people who tried. He was working.

He was getting better. He wasn’t getting famous.

And then he did something that no comedian had really done.

He took the internet seriously as a tool for building a direct relationship with an audience. He built a website, DaneCook.com. He funded it with $ 25, 000 of his own money, reportedly, which is a hell of a lot of money a quarter century ago, pulled from savings and retirement accounts, and launched DaneCook.com as an interactive platform where he could post content, interact directly with fans, and distribute his material outside the traditional club-to-album-to-television pipeline. This is like before iPhones and YouTube, right before that. Other comedians mocked Dane Cook for that.

The mocking was pretty direct and pretty widespread. The idea that building a website was a legit career strategy was not a popular one with the comedians in the early 2000s. The way you did it? Clubs. Then maybe late night, maybe you get an album, Comedy Central, something like that.

Dane Cook’s website was seen as a symptom of someone who didn’t know the rules rather than someone who would correctly identify that the rules were about to change. Then Dane Cook built a MySpace page. You forget how huge this was. By the mid 2000s, Dane Cook’s MySpace had over one and a half million friends, which was different from how the algorithm works today with passive followers. You know, these were people who had sought him out, added him as a friend and were engaging with content Dane Cook was putting out directly.

Dane Cook was answering emails. He was posting bits. He was building the kind of direct audience relationship that music was going through with Napster and file sharing, and the comedy industry hadn’t yet fully absorbed this as a concept. Dean Cook wasn’t waiting for someone to tell him he was ready. He was building an audience that would make his readiness self-evident.

His first album, Harmful of Swallowed, came out in 2003 and went platinum. Not immediately. It built slowly through the website, word of mouth, college campuses. The one that broke everything open was Retaliation in 2005. It debuted at number four on the Billboard 200 on the main chart, not the comedy chart, not the little charts, the main one, number four overall.

It was the highest charting comedy album since Steve Martin’s A Wild and Crazy Guy in 1978. It went double platinum. It was being quoted in dorms and cars and cafeterias across the country in a way that comedy albums really hadn’t done in quite a while. The Kool-Aid bit, the friend who’s the bad luck guy in every group, These were bits that college kids in 2005 could recite from memory the way previous generations like me could recite Monty Python and Eddie Murphy. The comedy world watched this happen and responded with some version of, that’s not real comedy.

I was running SiriusXM comedy in those days, and with the comedians, if you weren’t standing in front of a brick wall or smoking a cigarette outside the comedy cellar at midnight, you weren’t doing it right. Then there was Torgasm in 2005. HBO. Yeah, HBO, and this is HBO in its heyday. Dean Cook takes three comedian friends on a 30-day college tour.

Do you remember who the friends are? Wait till you hear who one of the friends are. I had forgotten who one of the friends are. I always think of Bobby Kelly, but there’s somebody who’s a bigger star than Bobby Kelly that was on this thing. I’ll tell you in a second.

Dean Cook takes three comedian friends on a 30-day college tour, films the whole thing. HBO turned it into a nine-episode documentary series that aired in the summer of 2006. The story is what the tour looked like from the perspective of the other three people on the bus. Robert Kelly, Jay Davis, and Gary Goleman. How does it feel to be.

Back in front of the cameras? I don’t feel any better than I did the last time I was in front of the cameras. I am insecure and vain and concerned that they’re going to make my nose look bigger than it really is. You ever drive by one. Of those things on the side of the highway and tell you how fast you’re going?

You know those things? You pay attention to them, man? You do? Can I tell you something? You don’t have to anymore.

I’m going to set you free. If you look very carefully, there’s a similar gadget in your dashboard. Think about that. Gary Goleman, the guy from The Great Depression, touring with Dean and Bobby Kelly and Jay Davis to Orgasm. In 2005, Gary Goleman had come off Last Comic Standing and had given him momentum and he was grinding.

I’m disappointed in the milk people and I hate Pepsi. Yeah, I used to be fine with Pepsi. I was like, okay, you’re there too, Pepsi. If I’m in a jam, I’ll use Pepsi. But then Pepsi started with this new campaign, the new advertising campaign.

Pepsi, it’s the cola. Oh, really, Pepsi? You’re the cola. Really? Pepsi, you just get to call yourself the cola.

You’re about as much the cola as rhubarb is the pie. Pepsi. You know it’s not the cola, because if you go home tonight and there’s an answering machine message on your answering machine, call me back, it’s the cola. I’m calling back Coke. He signed on to Tourgasm because he and Dane had been friends since the mid-90s when they met on the Boston scene, and because when HBO says, hey, HBO documentary, you don’t say no.

Now, from what I read, when Gary said yes, he didn’t know that the tour was being shot on spec, which meant no network deal yet, no budget beyond what Dane himself was funding out of his own pocket, the bus, the cameras, the whole thing. Dane’s money, Dane’s gamble. Goldman said years later he had no idea anyone was ever going to see the footage. Dane was filming it either to sell it to his fans on the website or sell it to a network. And by the time the tour ended, he was, in Goldman’s own words, the flavor of the decade.

Boy, that is a great description. People going crazy to work with Dane Cook, HBO buying the footage, the whole thing becoming a real TV series. Goldman described the experience as miserable. He left the tour partway for reasons that were never fully explained, then came back. The show labeled him, quote, the conflicted Gary Goleman.

Goleman eventually got the Great Depression. Robert Kelly built his own podcast and live career. Jay Davis worked the clubs. What they need to. Do is name these hurricanes after someone mean, scary, somebody you don’t like.

They should name the next hurricane after my ex-girlfriend. Yeah, they should call it Hurricane Bitch. Dane sold the footage to HBO and played Madison Square Garden. That’s basically all four trajectories you could have had right from that tour. HBO then gave Dane Cook Vicious Circle, a stand-up special filmed in front of 19,000 people at Boston’s TD Garden in 2006.

An arena, not a theater, not a big club, an arena, a stadium, Celtics, Bruins, huge. Dane performed in the round, the stage in the center, the audience surrounding it on all sides. Dane Cook sold out Madison Square Garden twice on the same day in November of 2007. That was before, like, everybody was selling out Madison Square Garden. That was a big deal.

He was only the second comedian to do it, the first Andrew Dice Clay in 1990. Now that we’ve mentioned Andrew Dice Clay, the comparison is worth noting because it’s not a flattering one in the cool kids of comedy. Dice Clay was another comedian who sold a lot of tickets to an audience that didn’t overlap with the critics and industry insiders who decided who counted. And although their material’s different, Dane Cook occupied a similar structural position. Massive commercial success, simultaneous with near-universal critical contempt from within the industry.

Dane Cook, nice to meet you. Excellent to be here. Everything has to be perfect for Dane Cook. I had Jesus up last week. There were sun chips waiting for me when I got here.

They knew that I loved sun chips, and they were there. This channel, Raw Dog, plays stand-up all day. I love your stuff. I know. I know.

You listen to Raw Dog? I do listen, yes. People love comedy. How many times? The first, second, third, fourth time.

Yeah. But we have bits in the computer that we have, and they don’t change unless you send. Us new ones. Right. Well, new ones are on their way.

Speaking of which, segue. Little gifties. You’re a huge movie star now, but you’re never going to quit stand-up. I can’t stay away, man. I love it.

Comedy is addictive. You can’t quit, right? No matter how big of a movie star you become, you can’t not go on. If I drive by a comedy club on the way back from set or whatever, and I don’t stop, I’m like, I could, try out that new bit that I ended up trying on, like, you know, the craft service guy. Because that’s what you end up doing.

You’re on a set. You start, like, you’re jonesing for stage time. Right. Anytime there’s a little crowd. I tried to relate just now to being on a set just now, by the way.

I just want to make a point. Yeah, I’m on set all the time jonesing for stage. Sorry. Tell us about the movie. You play a dentist in this movie.

Yes. I had the weirdest question. Yeah, no, no. Were they like, were they like, we’re looking for an actor for this movie who wants to play a dentist. We like Dane Cook, but we got to see his teeth first.

Well, no, but I am a method actor, so I actually went to dental school. It’s been. It was an exhaustive six month process. Six months. Phoenix Online must be like an online dental school or something.

In 2006, the AP ran a piece that was asking a question. Is Dean Cook actually funny? Jim Brewer, who at the time was hosting a daily show on Sirius Satellite Radio for the Raw Dog Channel, of which I was the boss and the guy that brought Jim Brewer in. That was called Jim Brewer Unleashed. And Jim gave the AP the quote they wanted.

He said, Everybody kills this guy. Not one comedian comes on my show and says I’m happy for him, which is weird. They can’t stand this poor guy. Brewer’s show had comedians on it constantly. Working stand-up comedians, touring comedians, people embedded in the actual circuit.

Yeah, like everybody did Brewer’s show back in the day. That was a big show. Prior to Howard coming to Sirius, Brewer’s show was actually the most listened to thing. Jim’s read on the consensus in the community was not the read of an outsider or critic. It was from a comic.

Jim acknowledged that Dane Cook was a tremendous performer. He separated the performance question from the material question and the character question. But Jim said a lot of comedians were upset because they feel this guy has snatched a lot of material, which bundled the aesthetic objection and the ethical objection. The Comedy World’s reaction to Dane Cook in 2006 wasn’t about the jokes. It was about the success, the success that came out of the Comedy World’s permission or endorsement.

It came from a website, a MySpace page, and college campuses rather than, you know, brick walls and cigarettes. The comedy world was watching somebody bypass its gatekeeping entirely, doing it at a big scale, and then getting accused of joke theft. My wife and I were thinking of having a baby, and I’d like to have a kid, because you can name your kid anything you want. I like that part. I’d like to give my kid an interesting name, you know?

Like a name with no vowels, maybe, you know? Just like, P-P-P-P-P-P-P-P-P-P-P-P-P-P. Just like 40 F’s, that’s his name. Go clean your room, you know, something like that. I’ve been thinking about kids.

I want to have like 19 kids. I think naming them, that’s going to be fun. Whatever the names that you come up with, that’s exciting right there. You get to both decide, hey, do you want to name that? No, I don’t like that name.

It’s like a little game you try to come up. I already have names picked out. I don’t even know. First kid, boy, girl, I don’t care. The first one that comes out, I’m naming it.

I think it’s beautiful. It’s feminine, but strong at the same time. Time for bed. The joke theft controversy around Dane Cook centered on comparisons between bits on retaliation and material that had appeared on Louis C.K. ‘s 2001 album, Live in Houston. Specifically three bits, including one called Itchy Butts, I’ll clean that up, where the similarities were specific enough that Louis C.K.

Publicly wrote in 2005, the year Retaliation came out, OK, this kid is stealing from me and making a lot of money. C.K. Said he wasn’t going to do anything about it. He wasn’t going to go to court over a bit called Itchy Butt, which is a very funny sentence and a principled position. But the accusation was out there and it landed in a comedy world that was already looking for reasons to get rid of Dane Cook.

And it became a defining part of how Dane Cook’s career was discussed for years afterwards, Dane denied it consistently and vehemently. Dane’s version was, the similarities were coincidental. Parallel thinking comedy is more common than people outside the industry understand that two comedians working similar life experiences will sometimes arrive at similar places without any contact between the comedians. Yes, parallel thinking happens. The comedy world knows it happens.

It happens more than audiences realize. But three incidents on two albums by two specific comedians is, you know, a math problem. What’s fascinating about all this is it sort of got resolved on television in public. In 2011, Louis C.K. Called Dane Cook four years after the accusations and asked if Dane Cook wanted to put it to bed in an episode of the TV show Louis.

Dane Cook said, yeah. The scene in season two, episode seven, is one of the more unusual pieces of television that comedy has ever generated. C.K. ‘s character, Louis C.K. Goes to meet Dane backstage at the arena Dane is headlining that night, and the two of them start talking about the accusations. In some dialogue that CK wrote and Dane Cook agreed to perform.

I don’t think that you saw me do those jokes and said, I’m going to tell those jokes too. I don’t think there’s a world where you’re that stupid or that. Bad a guy. I think you saw me do them. I know you saw me do them.

And I think they just went in your brain. And I don’t think you meant to do it, but I don’t think you stopped yourself either. And that’s why I never felt the need to help you not be hated by a lot of people. You know, the one thing that like really just gets to me is the whole thing about, um, people saying that I stole the joke about the itchy asshole because I get an itchy asshole a lot. So for you to think that you’re the only person who got an itchy asshole in America, I mean, like that’s, that’s bullshit.

You should try a natural laundry detergent. What? Cook later said the call from C.K. Aston to do the episode was a relief. It was so old hat.

It was pretty boring. And he was getting tired about getting asked about it. C.K. Said he didn’t think Dane had stolen from him knowingly. He thought Cook got some of his jokes in his head and got sloppy and that he’s a good guy.

The comedy community largely accepted it and moved on. The Internet did not because the Internet doesn’t move on from anything. And here we are today rehashing this.

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And then there’s the thing that puts Dane Cook in the news right now.

The brother. Between 2004 and 2008, Daryl McCauley, Dane Cook’s half-brother who had grown up in the same house, apparently was stealing from Dane Cook. Not skimming, not creative accounting, but doing withdrawals of $ 20, 000, $ 50, 000, $ 100, 000 at a time from Dane Cook’s accounts. We’re told there were forged bank statements, checks written to himself. It was discovered and resulted in a total theft of at least $ 12 million.

Dane Cook believes the actual number is higher and some is still unaccounted for. Funny Money, the Dane Cook story, takes a look at this. It will debut September 29th. McCauley was ultimately arrested in 2008 and charged with stealing $ 12 million from Dane Cook. While acting as his business manager, he pleaded guilty to larceny, embezzlement, and forgery in 2010 and was sentenced to five to six years in prison.

He was also ordered to repay the $ 12 million to Cook. Dane Cook describes him in the documentary as a person who spent time pretending he was something he wasn’t, which is a pretty remarkable sentence to applaud your own half-brother. The timing of the theft means it happened during the exact years of Dane’s greatest commercial success. The arena tours, double platinum album, the HBO deals, the garden. When we watch this thing on September 29th, we’re not sure if it’s a closure document or a reopening of a wound.

There’s an unresolved ending. The brother who took the money and vanished. Makes the story feel unfinished rather than settled. So how does Dane Cook fit in the comedy conversation in 2026? Strangely to me, he’s not in the regular rotation of names when people discuss the greatest stand-ups of his era.

Like if we look at the first 26 years of this century, I think I rate him a lot higher than most of the comedy snobs would. The critical consensus that formed against Dane in the mid-2000s was never fully reversed. There’s the joke theft controversy and, you know, the whole like, oh, it’s just a MySpace comedian kind of thing. His film career, which looked like it might do pretty well, the guy was a really nice-looking guy, a lot of charisma, funny, super popular, filling out arenas, did okay. He was the most talked-about comedian in 2006, and we don’t really talk about him now.

What shouldn’t get lost is what he did, the thing that everybody ripped him for. He looked at the internet in 2001 and understood it was a machine for building direct audience relationships outside the industry’s permission structure. He built one and worked it at a scale that nobody’s predicting. And it made people uncomfortable for reasons that had much to do with jealousy as with aesthetics. I mean, you know, you look today and you see like a comedian like I’m just a random name, Tom Segura, publishing outside the system.

And everybody goes, oh, great. Dean Cook did it first. Jim Brewer said it. Not one comedian comes on my show and says I’m happy for him. The comedy world was not happy for Dean Cook.

It’s funny. You live long enough and you become the thing you hate. The other brick wall comedians might want to look in the mirror. That’s your comedy news for today.

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