Comedy Central Roasts, Ranked by Sheer and Utter Brutality

22 Drew Carey

The first New York Friars Club roast ever aired on Comedy Central was hosted by cuddly Ryan Stiles, certainly capable of a witty line but not one prone to gouging someone’s eyes out. Even Roastmaster General Jeff Ross pulled his punches, letting Carey have it by calling him “the lovechild of Buddy Holly and Barney Rubble.” Funny but just a flesh wound. “Drew Carey is to comedy what Mariah Carey is to comedy” was about as mean as this one gets.

21 Jerry Stiller

TV son Jason Alexander took on the hosting honors because actual son Ben was clearly too big a star for that bullshit. Susie Essman summed up the mood nicely when she told Stiller, “You’re so cute and adorable, I find it hard to say mean, sexual things about you.” That didn’t stop her from ripping a new one for most everyone else on the dais, but Stiller remained relatively unscathed.

20 Jeff Foxworthy

Listen, how would you roast Foxworthy? Sure, his “you might be a redneck” routines are formulaic and hacky, but Foxworthy seems like a nice, decent sort, making him a  tough target for cruel jokes. And when roasters include Bill Engvall, the guy who has to get back on the Blue Collar Comedy Tour bus with Foxworthy after the show, you know the punchlines won’t land too hard. Speaking of which, here’s Engvall: “If you’ve shot everything but a successful TV show, you might be Jeff Foxworthy. Near the end, he wanted me to be on the show. That’s like being the fifth pallbearer for a four-handle casket.”

19 Hugh Hefner

Jimmy Kimmel, a guy we can imagine sneaking into a few Playboy Mansion parties, presided over a Hefner love-fest. Apparently, the worst the comics could do was accuse Hef of being old and surrounded by naked women. “When Hugh Hefner is in bed with a woman, he can make her scream,” joked Gilbert Gottfried. “She screams out, ‘Is he breathing?!’” That’s not to say the night was brutality-free. Gottfried either killed his career or turbo-charged it with his 9/11 joke, introducing the concept of “too soon?” to the national comedy lexicon.

18 David Hasselhoff

Hasselhoff had a ball as roasters told him he wasn’t an award-winning actor. Yeah, no kidding. Oh, and Germans like him. Zing!

17 Rob Reiner

Al Franken, a former United States senator, accused national treasure Carl Reiner and his celebrity pals of anal-raping baby Rob. Disgusting? Yes. Tasteless? Absolutely. But it was all shock value and too inane for Reiner to ever take personally.  

16 James Franco

Franco’s roast was utterly toothless, mainly because it was recorded a few years before five women, most of them students at his “acting school,” accused him of sexual impropriety in 2018. He’s barely worked since. But back in 2013, the worst roasters could do was mock him for a lousy job hosting the Oscars. We doubt any of these lines left a mark. Case in point: “Just remember,” joked Nick Kroll, “if anyone bombs here tonight, they’re just doing an impression of James Franco at the Oscars.”

“Everyone is gonna make fun of James Franco for the Oscars, it’s obvious,” added Jonah Hill. “Everyone was saying James was dead up there! But I think that was Anne Hathaway’s fault. I mean, fuck her for trying, like, at all!”

Ouch?

15 Denis Leary

Outside of South Park reruns, the Leary roast earned the biggest ratings ever for Comedy Central. But since Leary produced the show himself, any extra-mean jabs were left on the cutting room floor. An example? Producers (i.e., Leary) edited out a comic razor blade from Lenny Clarke, who told Leary that the late Bill Hicks left a carton of cigarettes for him backstage with a note attached: “Wish I had gotten these to you sooner.”

14 Bob Saget

Saget suffered during his roast — not from heartless insults but from Norm Macdonald’s maliciously corny putdowns. This was a whole different kind of brutality, and it hurt so good.

13 Flavor Flav

Flav’s roast was more cringey than cruel, with white comics choosing to focus on the Public Enemy alum’s skin color. “Flavor Flav is so skinny and Black,” joked Kimmel, “he looks like a Make-a-Wish kid whose last request was to try on a wetsuit.” Greg Giraldo piled on: “You are one Black motherfucker. You look like a skeleton wrapped in electrical tape.” Surely, Flavor Flav’s over-the-top antics gave comics more to work with than “you’re really Black!” 

At least this dude was into it. (Carrot Top was not.)

12 Bruce Willis

This was about the point when Comedy Central roasts stopped being about the celebrity’s friends poking their pal and more about up-and-coming comics throwing punches at someone they never met. “A lot of people don’t know that Bruce is a very talented musician,” joked Nikki Glaser, “because he isn’t.” No tears spilled here — what did Willis care about what unknown Glaser had to say? I preferred the personal punches thrown by Demi Moore, although they were more affectionate than atrocious. 

11 Pam Anderson

Not all celebrities ask, but apparently, roastees can declare certain topics as no-go zones. For Anderson? No jokes about Hep C. That still gave roasters plenty to make fun of, but two targets in particular took the spotlight. “People say, ‘Pamela Anderson’s nothing without her tits!’” declared Sarah Silverman. “And that’s not true! She’d be Paris Hilton.”

10 Joan Rivers

No jokes about Melissa! That was Rivers’ request and the roasters honored it — for the most part. Tom Arnold did chide Rivers’ daughter, but it was more of a self-own: “I’m not trying to be judgmental,” he said. “I just hate when someone uses a much more famous relative to further their career, Melissa — that’s my game, bitch.” 

Rivers herself was old school when it came to nasty insults. Jeff Ross took an easy age shot with this zinger: “This isn't a roast, it’s an autopsy!” But when the crowd started coming at Ross for being too mean, Rivers fired back at the crowd: “Ohh, it’s funny!” She also fired back at Kathy Griffin with a right cross to the cosmetic surgery.

9 William Shatner

Some roast subjects are clearly beloved by the roasters — e.g., William Shatner. You think an old-school nerd like Patton Oswalt was going to take serious shots at Captain Kirk? Old castmates showed up for the fun, too, even ones like George Takei with whom Shatner had long-standing beef. “Despite our tensions, I’m honored you invited me to be here tonight,” Mr. Sulu said graciously. “I can finally say what I’ve waited 40 years to say: Fuck you and the horse you rode in on!” But Takei couldn’t hold a candle to the night’s most abusive roaster, the murderous Betty White.

8 Alec Baldwin

Occasionally, it’s not the roastee who endures the most vicious comic jabs but someone else on the dais who’s an easier target. For the Alec Baldwin roast, that someone was Caitlyn Jenner. Entertainment Weekly’s rundown of the show’s “most brutal jokes” were mostly aimed at her, including:

• Nikki Glaser: “Caitlyn, I know you’ve only publicly identified as a woman for a few years, but I just want you to know that I know deep down, you’ve always been a c—. I spell it with a ‘K,’ though, for you.” 
• Chris Redd: “Hey, Caitlyn, you goddamn hypocrite. You’re like against gay marriage, and you voted for Trump — you’re like the Auntie Tom of the trans community.” 

Even Baldwin took the baseball bat to Jenner: “You look like a Real Doll that’s been fucked a littttle too close to the fireplace.”

7 Larry the Cable Guy

When Marcia Brady is one of your roasters, you’re not going to get too many scars. C’mon, it’s Marcia Frickin’ Brady!  

As it turned out, though, Marcia Brady was a killer: “I remember one traumatic time in my life when Marcia Brady got braces. Now Larry, braces are the things we use to straighten our teeth with. No? Okay, teeth are those yellow things in your mouth that you’re supposed to clean. Cleaning is what you do when you’re supposed to have respect for yourself. And Larry, respect is what you traded for fame when you made your deal with Satan.”

6 Roseanne Barr

Barr’s roast was “tamer than most recent roasts,” according to Entertainment Weekly, mostly focusing on jokes that said “she’s overweight” or “she’s a has-been.” Relatively safe territory, but here are a few decent shots:

• Katey Sagal: “It’s great to see Roseanne back in the spotlight. Technically, it’s two spotlights, but you get the idea.”
• Wayne Brady: “Roseanne, it’s been said that you stole Sam Kinison’s style: You’re fat, loud and you died in the ’90s.”
• Carrie Fisher: “You’re a follower of the Kabbalah, which is a form of Jewish mysticism. You know what else would be a form of Jewish mysticism? Hollywood giving you another show.”

Gilbert Gottfried, as always, brought it, too.

5 Donald Trump

Everyone gives Saturday Night Live grief for “normalizing” Donald Trump as a presidential candidate. Why not Comedy Central, which gave Trump the dais just a few years earlier? Maybe because the roasters did more than tussle his hair and poke fun at The Apprentice. A few choice sticks in the eye:

• Gilbert Gottfried: “As a developer, Donald Trump has done so much damage to the New York skyline that instead of calling him The Donald, they should call him the 20th hijacker.”
• Larry King: “Donald Trump, without a doubt, you’re a New York landmark. Which means it’s only a matter of time before you bulldoze yourself to build some gaudy, tacky monstrosity, and put your name on it.”
• Seth MacFarlane: “Donald, as long as I have you here, it’s pronounced ‘huge,’ not ‘eyuge.’ And here’s another one, it’s pronounced ‘I am fucking delusional,’ not ‘I am running for president.’”

4 Charlie Sheen

After his roast, Sheen invoked the Ron Burgundy School of Street Fighting — leave the mothers out of this. (Post-taping, he asked that jokes about his mom be edited out of the broadcast.) Otherwise, it was hard to make a bigger fool of Charlie Sheen than he was doing to himself with his “Winning!” videos in the early 2010s. The roast’s best joke was courtesy of Amy Schumer: “You’re just like Bruce Willis — you were big in the 1980s and now your old slot is being filled by Ashton Kutcher.” 

Another insult was never seen on TV (a la the mom jokes), courtesy of Steve-O: “The last time this many nobodies were at a roast, at least Great White was playing” (a reference to a Rhode Island nightclub fire that killed 100 people). Steve-O came to his senses and asked Comedy Central to cut the line before broadcast.

3 Rob Lowe

Lowe’s roast was shocking for the frivolity of its underage sex jokes, courtesy of a Lowe sex scandal back when those episodes were more easily swept under the rug. “Rob was in Austin Powers 16 years ago,” said David Spade. “Can you believe it’s 16? Or as he calls it, 18.” Spade wasn’t done either: “Rob has been called the comeback kid. No, I read that wrong. Rob has come on a kid. Glad we got that out of the way.” 

Nikki Glaser kept the pedo party going. “Rob defies age... restrictions. Really, you’re a fucking Adonis. I hate you. You look like you’re sculpted. You put the ‘statue’ in ‘statutory rape.’ God, I had such a crush on you when I was a little girl. If only I’d known that’s when I had my best shot.”

But that’s not what made the Lowe roast so brutal. For some reason, Ann Coulter decided taking part in a roast would be fun, not realizing she would be the favorite target of the night’s nuclear bombs. Her forced, frozen smile and dead eyes haunt me to this day.

2 Justin Bieber

God bless Hannibal Buress, celebrity truthteller. Bill Cosby would likely still be selling Jell-O Pudding Pops if Buress hadn’t insisted on repeating what we all should have seen. And when it comes to Bieber? Buress was cold-blooded, not just insulting but completely honest. 

The whole event was orchestrated so that Bieber could apologize for his years of entitled, bratty behavior, which, of course, all the comics immediately honed in on. 

1 Chevy Chase

Comedy roasts are only truly heartless when the jokes hit a vein. And no one appeared more wounded at his own roast than Chevy Chase. “The night’s vituperation, a third of it deleted by the censor’s screech, recalled Lord of the Flies,” wrote Slate. “Even by roast standards, this night was venomous.”

Per Entertainment Weekly, Chase himself considers this roast the moment in his life when he hit rock bottom. “Total strangers telling him that his movies were crap, his talk show was a comedy abortion, he had never been funny. Total strangers giggling about his addiction to drugs. There was no warmth in their comments. … Everyone agreed without even having to think about it: Chevy Chase was a bastard.”

Host Paul Shaffer even went to Chase’s hotel room after the event to console him. It didn’t help: “Shaffer left, and Chase sat by himself in the dark. Crushed.” 

I’d feel bad for the guy, but Chase and his history of being terrible probably deserved it.