It is as old as TV itself: Take a star, one who’s been around long enough to make friends and enemies; sit them in a throne; wheel in a podium and a wet bar; and remove gloves. You hit that resilient, beloved figure with hard truths, cold lies, and raw abuse. The star feels bruised and dizzy but somehow honored, and everyone walks away happy. By 2003 the old ritual was dead, but a decade on, Comedy Central’s improbable modernization of the roast is now both a reliable ratings juggernaut and the greatest comedic-talent-breaking platform since the Carson-era Tonight Show or Saturday Night Live.
Still, back in the mid 1990s the mention of a “celebrity roast” brought to mind either the annual New York Friars Club Roast (fiercely private and often filthy) or the Dean Martin Celebrity Roasts (shticky, corny black-tie affairs televised on NBC in the ’70s and early ’80s). In other words, roasts were not hip.
Gilbert Gottfried (roaster): I watched the Dean Martin roasts. Back then mentioning a nudist colony counted as a dirty joke. Just saying something like “sleeping in the nude” was like talking about the strangest, most perverted act.
Doug Herzog (former president of Comedy Central, now president of Viacom Entertainment Group): In 1995 I’d come over to Comedy Central from MTV, where there were events like the VMAs and Spring Break. I thought, We need a comedy event. A one-night-only kind of thing. I grew up watching the Dean Martin roasts, so that was at the back of my mind. And living in New York, I’d sometimes attend the Friars roasts. They were filthy. Unairable. We had to figure out a way to combine the two.
A deal was brokered between Comedy Central and the Friars to broadcast the latter’s annual roasts on the network. The partnership lasted a few years, skewering the likes of Drew Carey, Hugh Hefner, and Chevy Chase before Comedy Central decided to go out on its own with the inaugural Comedy Central Roast in 2003, featuring roastee Denis Leary.
Doug Herzog: Denis Leary is a gigantic fan of Dean Martin, and I think he wanted to re-create that Rat Pack vibe.
Denis Leary (roastee, producer): Once my career took off, I became friends with Dean, which was really weird. He reached out and said, “Come to my house for dinner.” Still to this day it’s the biggest deal to me, even though he called me a pussy for nursing a beer the entire night. Anyway, with the roasts we were gonna inject some new blood into it. The set. The music. Sort of rock’n’roll.
With Leary on board, the stars came out: Kiefer Sutherland, Elizabeth Hurley, Christopher Walken, Jon Stewart, Conan O’Brien. The dais also showcased comics from the Boston stand-up scene where Leary began: Lenny Clarke, Nick DiPaolo, and a young Dane Cook. Jeff Garlin served as Roastmaster. The Leary roast was raw in a way the others hadn’t been.
Denis Leary: The harder they hit you, the more info about them you’ll break out. Comedians bust each other’s balls, and I come from that neighborhood, so busting balls is everything.
Nick DiPaolo (roaster): What I found most awkward is that I’m ripping people whose careers were 40 times more successful than mine. But if you’re a decent comic a roast is easy. You don’t have to learn insults. It’s in your DNA.
The odd mix of stars, up-and-comers, has-beens, and never-weres continued in the second roast, produced by Leary and “honoring” Jeff Foxworthy, who was coming off the Blue Collar Comedy Tour with fellow “clean” comics Bill Engvall, Ron White, and Larry the Cable Guy.
Jeff Foxworthy (roastee): They were paying me good money to do it, so I thought, Yeah, I’ll let ’em roast me, and I’ll give the money to charity.
Denis Leary: Jeff is a really sweet guy, and he got wind that Bill Engvall and a couple of his Blue Collar buddies were going to be on, so he seemed a little like, “Hey, this is gonna be great!” And I said, “Hang on a second. You better be prepared.”
Jeff Foxworthy: Five minutes into the roast, I remember thinking, If my mother is watching this—the EMTs have her on the floor pumping her chest right now…
Bill Engvall (roastmaster, roaster): I love a good dirty joke as much as the next person, but after an hour of it? Good night! Stuff I’d be hesitant to say in a poker game with my buddies, all of a sudden people are just babbling on TV? I was sitting right next to Jeff, and I could feel his uneasiness.
Jeff Foxworthy: Ron White called my mustache “prison pussy.” That would have been the one that sent my mom off the couch and into the coffee table.
Larry the Cable Guy (roaster, roastee): I don’t mind dick jokes. I don’t mind it if it’s dirty, but if it’s dirty just to be dirty…After the Foxworthy roast, production moved from New York to L.A. to honor Pamela Anderson and introduced a bigger stage and bigger stars. Herzog finally had his tent-pole event, complete with a new “Roastmaster General” in Jeff Ross and a hot mess in Courtney Love.
Anthony Jeselnik (writer, roaster): Ross is like the fucking Godfather.
Joan Rivers (roastee): I think Jeff Ross should have emerged years and years ago. He’s had a long wait.
Jeff Ross (roaster): The “Roastmaster General” was something I think Jimmy Kimmel called me first. I feel like it’s more of a nickname than a title.
Joel Gallen (executive producer and director): Courtney Love was one of the first people Pam wanted on the show; at the time they were buddies. Courtney was not an easy booking—she passed a few times.
Nick DiPaolo: She had supposedly kicked heroin, but she was sweating like Moses Malone at the foul line.
Lisa Lampanelli (roaster): I don’t drink; never have. I’m no nun. My addictions have always been food and men. But the Pam Anderson roast sucked because Courtney Love was wasted! Still, she acted like such a fool, it made CNN, and everyone watched the roast.
But with Anderson, and subsequent roastees like William Shatner, producers would learn just how far was too far.
Lisa Lampanelli: During the Pam Anderson roast, some comic went on a tirade about Pam’s vagina, and it was just not funny. There’s nothing funnier than a good vag joke, but it went on way too long and every joke was lousy. She honestly looked like she was going to tear up, and I was so angry. I saw her look at Tommy Lee, and he mouthed to her, “Are you OK?”
Anthony Jeselnik: With Shatner, his wife had drowned, so of course I wouldn’t fucking bring that up. When Mike Tyson was on—don’t make fun of Mike’s kid who died on a treadmill. Of fucking course not. As mean as I am with these things, I never make fun of a dead kid or a dead relative.
William Shatner (roastee): [Being roasted] sounds like great fun, and ultimately it is, but unless you’re set mentally and emotionally, it could have a nightmarish quality to it. It could be like a bad dream where people are poking fun at you in public. It’s not different from being in a torrid love affair—just let yourself go…
Jeff Ross: At the Shatner roast, I had some jokes about Farrah Fawcett, how I was in love with her as a kid and how I had her poster and would fantasize to her, and then I said, “But now you look like…” whatever—jokes about her being old and ugly. I get there, and she’s old, but she looked fantastic! The 12-year-old in me came out, and I got shy and said, “I’m not calling her an old beast and an old hag. She’s gorgeous! I still want to fuck her.”
As with the Pam Anderson roast before it, the Flavor Flav roast in 2007 posed a challenge to make sure that the dais presented a good balance, both racially and sexually.
Doug Herzog: I’m always personally very conscious when we have women—it can’t be a dais full of guys. That just feels bad. Keeping a balance is important.
Jeff Ross: The Flav roast was coming off the year of the terrible Michael Richards thing, where he kept yelling the N-word in a comedy club. Racial humor was really under a microscope.
Joel Gallen: Flavor Flav’s comedic timing was so hyper at that point, and he was so nervous, that even though we worked with him on the best way to deliver a joke, I remember him laughing almost before he’d deliver the punch line. We had to work some pretty major surgery in editing.
Flavor Flav (roastee): It was only later that I realized I came from this world. I was born and raised “playing the dozens,” and honestly, my first time having a roast, I didn’t actually know what it consisted of. If I’d known it consisted of me being able to tell my own jokes and do my thing and just play the dozens? Oh, man, I would have creamed those guys. I wanna do a part two. I wanna call it Flav’s Revenge.
For the next roast, honoring Bob Saget, producers filled the stage with heavy-hitting comics like Norm Macdonald, Gottfried, Greg Giraldo, Ross, Jim Norton, Susie Essman, Jon Lovitz, Sarah Silverman, Lewis Black, and the king of the insult comics, Don Rickles.
Bob Saget (roastee): I was pensive at first, wondering what factor they were going to rip apart the most. They always go after your career—or whatever lascivious behavior you’re known for. But in this case I was concerned about people I’ve worked with. Especially the young people.
While there was no shortage of Olsen twins jokes, the highlight of Saget’s roast was when pal Norm Macdonald returned, briefly, to the corny, prime-time-safe humor of a more innocent age: “You’ll never be over the hill, not in the car you drive.” “She may be a vegetarian, but she’s still full of baloney in my book.” Not everyone grasped the concept. Those who did were in tears.
Bob Saget: He made a creative choice. I talked to him the week before. I said, “Norm, what do you want to do?” and he said, “Aw, I can’t make fun of my buddy. I’m just gonna tell old jokes. Really bad old jokes. Jokes from, like, 200 years ago.”
Jon Lovitz (roaster): He was just doing it to be different from everybody else. “They’re being as dirty as they can? I’ll tell the corniest jokes possible!”
Filling the “crazy old lady” spot was Oscar-winning actress Cloris Leachman, who reminded many of her comedy cred.
Bob Saget: “I am not here to roast Bob Saget. I’m here to fuck John Stamos!” That’s something you want to read under someone at Mount Rushmore, a very lovely and iconic thing.
Cloris Leachman (roaster): I didn’t even know who Saget was. Or John Stamos. You get a call from your agent—they deal with it. I show up, walk in, and read. Period. It leveled the room. It leveled me too.
The next few roasts, skewering Larry the Cable Guy, Joan Rivers, and David Hasselhoff, featured the usual mix of celebs and roast stars, including Ross, DiPaolo, Giraldo, and up-and-comers like Whitney Cummings.
Doug Herzog: No matter who it is, there are a few things you know about that person, and that will inform every joke. With Hasselhoff it’s Baywatch…hamburgers…
Gilbert Gottfried: The Hasselhoff roast was an extra treat, not only because I could do jokes about David Hasselhoff, but, since he’s beloved in Germany, I could throw in a few Holocaust jokes.
The Hasselhoff roast saw the rise of Roastmaster Seth MacFarlane. Known at that point only for Family Guy, he would emerge as the quintessential master of ceremonies (before going on to host Saturday Night Live and the 2013 Academy Awards).
Doug Herzog: He brings that Dean Martin, Rat Pack, martini, tuxedo vibe. We like to think we were his stepping stone.
Jon Lovitz: That guy is one of the most talented people ever in Hollywood.
Jonas Larsen (senior VP of Comedy Central specials): As a matter of fact, we’re not only gratified, we take full credit. When Seth got the Oscars gig, I sent his manager an e-mail that said, “You’re welcome.”
Shortly after the Hasselhoff roast, tragedy struck with the overdose of roast regular Greg Giraldo, who’d long fought addiction.
Lisa Lampanelli: I had my issues with Greg. It’s documented that Greg had serious drug and alcohol problems.
Barry Katz (talent manager): Greg was in his own battle. For him it was weird. He was a guy who was so well-respected, but for some reason, career-wise, it just wasn’t happening the way it should have.
Jeff Ross: Comedians are comedians. We’re comedians before we’re Jewish or Italian or Irish or black. We’re comedians—that’s our family, that’s our religion. When you’re working at the level that Greg was, a lot of people care about you. We don’t get over it, but we get as close as we can by doing another roast.
Gilbert Gottfried: When I heard about Greg, I immediately tweeted “If Greg Giraldo is cremated, will that be the Greg Giraldo roast?” It seemed like a fitting tribute to a roaster. It was sad, but you had to make jokes about it anyway.
The roast of Donald Trump in 2011 saw a move back to New York City and the biggest bomb in the show’s history, courtesy of Mike “the Situation” Sorrentino.
Donald Trump (roastee): They’d approached me a number of times—and eventually I said yes. I knew what I was getting into, but I also knew that we would raise a tremendous amount of money for charity. We raised a million dollars.
Lisa Lampanelli: When the Situation went up, I was sweating like Sandusky at a Cub Scout meeting. But he’s so frickin’ delusional, he comes up afterward and says, “That was pretty good, right?” I said to myself, “Dude, you got booed so loud [roaster] Marlee Matlin heard it, all right?”
Joel Gallen: He just was not funny. Didn’t get how to deliver a joke.
Donald Trump: I thought he was terrific, frankly. He was so uncomfortable that it really became funny. But he took a tremendous amount of abuse.
Perhaps the greatest endorsement of the Roasts’ reach and power arrived later that year, courtesy of the “Warlock From Mars” himself, Charlie Sheen, who turned to the dais to neutralize his unprecedented public meltdown.
Doug Herzog: Charlie Sheen was one of the guys we asked for years who said no, so that was like roast-Christmas.
Jon Lovitz: With Charlie it was kind of like, “Roast me because I really have acted up, and I have a sense of humor about myself.”
Anthony Jeselnik: Sheen was a smart guy who knew how to play it. He handled the roast perfectly.
Jonas Larsen: Almost instantaneously, his scandal went away. Once he went out and took every hit based on the spectacular five months of entertainment that he provided, it went away. It became the perfect place for him to wipe the slate clean and get on with his career.
The highlight of Sheen’s roast was Patrice O’Neal, who, with more people watching than ever before, went on the attack.
Joel Gallen: We put him near the end of the show and [after getting hit] he shifted his gears and started roasting the roast. When a comedian can do that in the moment, it’s brilliant. Not everything that he said was hilarious. But it was really honest.
Amy Schumer (roaster): I was like, I’m going to bring it the hardest to him, and I’m going to say the meanest jokes I think of (“Tonight is not just the roast of Charlie Sheen; it’s also a farewell party for Patrice’s foot”). He was very, very proud of me and made me feel like I impressed him that night.
William Shatner: When we went out to the parking lot, I knew Patrice had diabetes, but I didn’t know it was fatal. As we’re waiting for the car, we start talking about life and death, and he starts to weep. And then I realized he knew how close he was to dying, and that last moment we were holding each other and crying.
O’Neal suffered a stroke a month later and passed away in November. With the loss of him and Giraldo, the roasts seemed to take a softer turn with the roast of Roseanne Barr in 2012, not necessarily for the better.
Lisa Lampanelli: I didn’t like it going kinder and gentler. I thought, This is going to be a ratings stinker. And it was.
Joan Rivers: Let me just say this: Comedy is here to take the humor as far as it can go. There’s no such thing as a line. If you’re going to be offended, go watch The 700 Club. Have your laughs there. You know, Harry Truman, who I slept with, used to say, “If you can’t take the heat, stay out of the kitchen.” We were on top of the stove when he said it.
A decade since the Leary roast in 2003, with roasting such a known quantity that Ross now hosts his own spin-off show, The Burn, on Comedy Central, where does the Roast go next? Who will step up for the tribute and the abuse? And will an increasingly unshockable and distracted public keep tuning in?
Anthony Jeselnik: I think that [for the next roast] they’re going to try to go back to the old tried-and-true, everybody-as-mean-as-possible thing. Their dream is to have George Clooney bring all his celebrity friends on and come do a roast.
Doug Herzog: We ask Howard Stern every year and he says no. He loves the roasts, but he doesn’t want to do it. Then again, why do it if you’re Howard Stern? Someone else we’d love is Lindsay Lohan.
Jeff Ross: When I started doing these roasts, it was like telling people I speak Latin or I’m into jousting. It was antiquated and corny. But now roasts are turning into a national pastime. I have 16-year-old kids imitating me! People are roasting each other in their backyards, at bachelor parties, at frat parties. I think these roasts are like the World Series or the Super Bowl: There are good ones and bad ones, but people remember them forever.
Want more comedians? Check out our interview with Tom Arnold and Jack Black Gets Roasted Alive.