Bring On the Haters: Dane Cook Is Plotting a Comedy Comeback

Greenblatt’s Deli, just next door to the Laugh Factory on Sunset Boulevard, has been raising the cholesterol levels of stand-up comics for 40 years. Jerry Seinfeld, Dave Chappelle, Kathy Griffin, Tim Allen — they’ve all scarfed down the restaurant’s famous corned beef sandwiches and noodle kugel during late-night after-show hangouts. And right now, sitting unnoticed in a booth, wearing a vintage Kenny Rogers T-shirt and slurping chicken noodle soup, is a comic who not long ago was one of Laugh Factory’s biggest draws. Indeed, Dane Cook at one time was the most successful stand-up on the planet, earning upward of $20 million a tour. Also, the most hated.

“It has to be authentic,” Cook, 46, says as he slowly stirs the soup in his bowl. “It has to be raw. I want people to feel like they’re seeing somebody talk about where they’re at now.”

He’s referring to his new act, which an hour ago he was performing in front of a Laugh Factory crowd of about 300. His material today is something of a departure from the punchline-free observational monologues he once delivered in front of sold-out mobs of frat boys in Madison Square Garden. There are more setups, more zingers, more jokes about aging than his usual bits about car alarms or public restrooms. But starting Feb. 20, he’ll be taking it on the road for his first major tour since 2013’s Under Oath. Yes, that’s correct: The most mocked and loathed comic of the past 20 years, a guy who’s been accused of joke-stealing by Louis C.K. (“100 percent nothing,” Cook says of the charges) and publicly taunted by the likes of Seth MacFarlane (via Family Guy) and Ike Barinholtz (via Mad TV); whose own brother betrayed him by embezzling millions; and whose name on internet comedy message boards was once all but synonymous with “douchebag” — that guy is about to attempt a comeback.

“From the outside looking at me, I would say this seems like a comeback moment,” Cook notes. “So, yeah, I guess we can call it a comeback. But for me, man, I feel like it’s been mostly a trajectory.”

Back when Cook was a boy growing up in Boston, he would stay up late to watch the comics on The Tonight Show. One evening, he turned to his mother and announced that he too would someday become a stand-up. “‘Yes,’ she said, ‘I can see that.'”

So, at 23, he moved to New York and began performing in clubs. A few years later, he moved to Los Angeles — where he still lives in a sleek, modern mansion in the Hollywood Hills, where he chills with his girlfriend, Kelsi Taylor, 20 — and started landing TV gigs. In 1998, he appeared on Comedy Central’s Premium Blend, which led in 2000 to a half-hour special on Comedy Central Presents, which ended up winning a Comedy Central stand-up showdown.

At one point, Cook nearly moved back to New York after he wrangled a tryout with Saturday Night Live (to fill Adam Sandler’s spot), but he had a panic attack before the audition. “I sat on a bench in front of Rockefeller Plaza with these Ray-Ban sunglasses on and tears pouring out of my eyes because I knew I wasn’t going to go in,” he recalls. No matter; in a few years, he’d be hosting the show (twice), landing HBO specials, getting cast in rom-coms like Employee of the Month and Good Luck, Chuck (with paydays approaching $5 million) and recording double-platinum albums like Retaliation, which in 2005 became the highest-charting stand-up record in nearly three decades.

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And yet, even as his career was soaring, there were doubters. Millions of undergrads and high schoolers might have thought Cook was a genius, but the Associated Press wasn’t so sure, publishing an article in 2006 titled, “Is Dane Cook Funny?” (its answer wasn’t entirely yes). The harshest critics were other comedians who couldn’t fathom why Cook’s seemingly jokeless material (“Ever notice how bathroom floors are always wet?”) could fill up arenas. “Some of his peers didn’t understand his comedy,” acknowledges Laugh Factory owner Jamie Masada, who has known Cook for 20 years. “He was selling out Madison Square Garden, and they were like, ‘Why can’t I do that?’ ” Agrees longtime Cook pal and fellow Bostonian Denis Leary: “In the world of celebrity, the more famous you get, the more friends you lose. And Dane’s success was so huge people were jealous in droves.”

Still, not all comics harbored disdain for Cook. Chris Rock made it a point to phone Cook after his 2006 special, Vicious Circle. “I called him because I liked it, but also because after I did my first big special, the thing that meant the most to me was when [Eddie] Murphy and [Jerry] Seinfeld called me and told me they liked it,” Rock says. “I’m not saying I’m on the level of those guys, I’m just saying it’s great to be acknowledged by people in your business.”

One of the early knocks on Cook was that he was a more talented promoter than comedian — and there’s no question he was savvy from the start about boosting his brand. He was one of the first comics to use the internet to publicize himself — first on sites like MySpace (“I remember getting ready to play Madison Square Garden, I posted once on MySpace and without spending a dime on any promotion or advertising, we sold out”) and Napster, then on his own website (Cook spent $35,000 to set it up, nearly every penny he had at the time). “Dane was a pioneer in using the internet,” says comic Sebastian Maniscalco. “I was in awe that he would reinvest into the marketing of it all.”

Cook himself was keenly aware of the mixed reactions his comedy was generating. “One person would be like, ‘Dane Cook, man, this guy’s funny! And then the next guy is like, ‘He’s a douchebag! Nobody likes him!’ But I was almost giddy to be that guy,” Cook says. “I was like, ‘Shit, it’s way cooler being Darth Vader than it is being Luke Skywalker.'”

But telling bad jokes is one thing, stealing good ones is quite another. And in 2005, just a few weeks after Retaliation dropped, while it was sitting high on the Billboard chart, Louis C.K. publicly accused Cook of lifting material from his 2001 album, Live in Houston. Cook categorically denied the charges and wrote a letter to C.K. asking him to stop bad-mouthing him, which C.K. ignored. “I think he knew that he could be more popular talking about why I shouldn’t be popular,” Cook says, offering his theory for why C.K. made the accusations. “It helped him, it really did. It was like he was on a press tour because of it.”

The plagiarism claims were just the start of a series of setbacks that pushed Cook off his trajectory. Months later, his mother, Donna, who’d been Cook’s biggest booster, died of colon cancer at age 66. Less than a year after that, his father, George, died of pancreatic cancer at 74. Cook, who says he has never taken a drink of alcohol or done a single drug, notes he and his father became close in the years prior to his death but were at odds most of his life because George was an alcoholic. “He brought a lot of turmoil into the house.” 

And then, in perhaps the unkindest cut of all, he learned, in 2008, that his half brother, Darryl McCauley — whom Cook had kept on the payroll as a business manager at $150,000 a year — had been embezzling, emptying Cook’s account of $18 million. Darryl ended up being sentenced to eight years in prison for the crime and has since been released; Cook says he’s since made up his lost fortune, but the betrayal still stings. “My brother died [to me] in that moment,” he says. The two have not spoken since Darryl was released. It was Cook’s friend and mentor, the late Jerry Lewis, who became his rock as he tried to pick himself back up. “Dane was like a son to my father,” says Lewis’ daughter, Danielle. “Dane reminded him of a younger version of himself — so eager and so goofy and so physical onstage.”

A lot of this trauma was processed on Cook’s 2009 Comedy Central special ISolated INcident, in which his act took a disturbing turn, with material based on the death of his parents and other dark matters. “I was just unhappy,” he says. “I didn’t have the same goals and purposes that I felt before. I wasn’t the same.” After the special, Cook made the decision to fire his longtime team — including CAA’s Jason Heyman — and reassess his career. “I just stayed in Los Angeles and did a lot of therapy,” he says. “I worked on the knots that were tangled inside of me, how to deal with grief, how to deal with betrayal, and [how to deal] with the ebbs and flows of what a career is.”

There were a few missteps along the way, and Cook owns them. The first occurred when he announced on social media in 2011 that he had auditioned to play Captain America in Marvel’s Captain America: The First Avenger. “Oh, I got in so much trouble,” he recalls. “I was feeling really excited, but it was supposed to be a quiet, private thing. I wrote an apology letter to the casting director because they were upset.” Then in 2012, he was flamed for making a joke about the Aurora, Colorado, movie theater shooting just a week after it occurred. Cook issued an apology shortly after cell phone footage leaked of the moment. “I’m not a malicious person,” he says. “When they put it on CNN and said, ‘This is outrageous,’ then I could look at it too and say, ‘Oh, of course. Yeah, this isn’t funny.'”

Cook went on tour again in 2013, did a 2014 Showtime special and took some acting jobs (in the 2015 bomb 400 Days and on Starz series American Gods) — but during the past five years, he mostly has stayed out of the limelight save for directing a recent short film, American Typecast, which screened at the Santa Barbara Film Festival. About the only headlines he’s made of late were when the tabloids learned that he’s dating a singer 26 years his junior (Taylor and Cook met when he hosted a game night for friends). “We laugh a lot about it,” Cook says of the eyebrows raised over their age difference. “We’re not afraid to goof on [that perception]. But I have never had somebody in my life who is so kind and caring. I hope it goes the distance.” 

The comic had tried to repair relations with C.K., appearing as himself on C.K.’s FX show in 2011, but the results had been mixed. “I wanted a couple of things tweaked [in C.K.’s script],” Cook says. “But he was not going to change anything. It was what it was.” Still, when reporters called Cook in 2017 looking to see if he wanted to dish out any payback when C.K. admitted to masturbating in front of several women, he kept quiet. “People were like, ‘What do you think about this guy?'” he says. “But I didn’t speak out. All I can say is that nothing Louis did to me is anywhere near what happened between him and those women. Yeah, it sucked what happened to me, but I knew what I did and didn’t do.” That said, Cook does twist the knife some with a C.K./karma joke in his current arsenal — a quip that got one of the biggest reactions during his Laugh Factory set.

As the deli bill is dropped off, the subject turns to his upcoming tour, Tell It Like It Is, which will cover 47 dates, with stops in Boston, L.A. and New York. No, he won’t play Madison Square Garden, but Radio City Music Hall isn’t bad. So far, tickets (going for as much as $185) have been moving briskly. “I used to not care [about sales],” Cook says. “But this time I do check. I get goose bumps.” According to Live Nation, which is promoting a large chunk of the tour, some dates are nearly sold out. “This feels good to me,” says Geof Wills, Live Nation’s president of comedy. “People want to see him. His fans love him. You tell me the definition of a comeback.”

The new tour, it turns out, is inspired by something Cook saw when he was a kid watching The Tonight Show with his mom. George Carlin was a guest, and he’d brought along a cardboard cutout of his Hippy Dippy Weatherman, a ditzy character that helped make Carlin famous in the 1970s. “He took out the cutout and said, ‘A lot of you guys might think this is me, but he’s not.’ And Carlin just let the cutout fall out of the frame. He literally killed the old version of himself on the air. I respected that. That’s how I feel right now. I’m in the transition. But it’s a great place to be. Because I have nothing to hide and it feels right and it feels good. It feels like I’m about to drop the cardboard cutout.”

A version of this story first appeared in the Feb. 13 issue of The Hollywood Reporter magazine. To receive the magazine, click here to subscribe.