Top 20 Celebrity Roast Moments: A Look Back at the Best One-Liners and Put-Downs

“20 Years of Celebrity Roasts: A Look Back at the Most Savage Moments”

We are in the third decade of celebrity roasts on Comedy Central. The TV event kicked off with a roast of Drew Carey at the legendary New York Friars Club in 1998 and has continued with targets ranging from athletes to musicians to actors to future Presidents of the United States. So with that in mind, it’s a good time to look back on the last 20 years of one-liners, put-downs, and cheap shots. Be advised, the roast can get very dirty, but this gallery is for an all-ages audience, so don’t expect to find Jeffrey Ross’ thoughts on Bea Arthur’s anatomy.

1. Bill Engvall on Jeff Foxworthy
It’s always satisfying when a roastee’s career gets shredded, but particularly so when it’s being done by a close friend. And it had to sting for Jeff Foxworthy that it came from one of the Blue Collar comedians who isn’t Larry the Cable Guy or Ron White. Bill Engvall laid into his buddy, saying, “If you’ve shot everything but a successful TV show, you might be Jeff Foxworthy,” and, “Near the end, he wanted me to be on the show. Yeah, that’s like being the fifth pallbearer for a four-handle casket.”

2. Greg Giraldo on Chevy Chase
The late, great Greg Giraldo was fearless any time he performed, whether it was on a roast (he did eight of them), a comedy club stage, or annihilating Denis Leary on “Tough Crowd.” There’s literally an hour’s worth of great Giraldo roast jokes, but he was particularly savage on the Chevy Chase Roast. Giraldo explained he couldn’t dream of Chase’s career — “making three great movies and 40 (crappy) ones.” And, the most brutal part, “You’ve made 40 movies, and Al Franken is the biggest movie star who showed up. An O.J. roast would have had more star power!”

3. Norm MacDonald on Bob Saget
During one of the dirtier roasts, complete with many unprintable lines about Bob Saget’s TV family. After an hour of jokes that wouldn’t even be printable in Playboy, Norm MacDonald got up and did the most subversive thing of all: He went clean. His entire routine was old-timey, corny jokes with the softest insults possible, “Bob has a beautiful face, like a flower. Yeah, CAULI-flower!” Norm even cut out words you can say on TV — “What the H” instead of hell. He clearly upended the roasts, but after all, aren’t you supposed to say nice things about your friends?

4. Jeffrey Ross on Pamela Anderson
The Roastmaster General, Jeffrey Ross has been producing the show since the Friars Club days. He’s great at saying the worst things about people but also making sure everyone has dinner, parties together, and stays friends. But during the Pamela Anderson roast — which was as much the roast of guest Courtney Love — Ross ad-libbed a gem: “How is it that Courtney Love looks worse than Kurt Cobain right now?” Love checked herself into rehab the next day. Ross says “Roasting saves lives.”

5. Snoop Dogg on Donald Trump
It feels strange that a “Roast” subject would end up in the Oval Office, but America is pretty weird in 2018. Nonetheless, even though Lisa Lampanelli declared that Trump had “ruined more models’ lives than bulimia. You’ve disappointed more women than ‘Sex and the City 2,'” the best line came from Snoop, who ominously predicted Trump’s presidential run by asking, “Why not? It wouldn’t be the first time he pushed a black family out of their home.”

6. Martha Stewart on Justin Bieber
The roast of Justin Bieber was designed to rehab Bieber’s image, but they found an unexpected comedy star in Martha Stewart, who roasted all the guests and poked fun at her own prison sentence. “Let’s get to the reason I’m here tonight which is to give Justin Bieber some tips to use when he inevitably ends up in prison. I’ve been in lockup and you wouldn’t last a week, so pay attention. The first thing you’ll need is a shank. I made mine out of a pin tail comb and a pack of gum. It’s so simple. I found Bubbalicious works best and it’s so much fun to say.” The show also reignited Martha’s friendship with Snoop Dogg and led to their VH-1 cooking show.

7. Anthony Jeselnik on Charlie Sheen
Anthony Jeselnik’s comedy is extremely dark even in his normal set, so it’s not a surprise he’d deliver the best line in the roast of a very dark individual Charlie Sheen. “The only reason you got on TV in the first place is because God hates Michael J. Fox.” He also said that every moment of Sheen’s life “feels like the first two minutes of ‘Law & Order SVU.'”

8. Amy Schumer on Charlie Sheen
Before she was an international sensation, Amy Schumer blew up on the roasts. Particularly the Charlie Sheen “Roast,” when she said his wives were like soldiers in Vietnam — “constantly afraid of being killed by Charlie” — and eviscerated him with “Charlie, you get a bad rap, but you’re just like Bruce Willis. You know, you were big in the ’80s and now your old slot’s being filled with Ashton Kutcher.”

9. Triumph The Insult Comic Dog on Rob Reiner
He hasn’t been back since the Rob Reiner “Roast,” but Triumph the Insult Comic Dog is the perfect member of a roast dais. His entire life is a roast! Robert Smigel’s creation zeroed in on his weight, but Triumph had a whole litter of fat jokes:
– “I’m actually sorry to see you showed up tonight — I won’t be getting any table scraps.”
– “You’re like Orson Welles, without all that genius baggage”
– “Even David Crosby thinks you’ve let yourself go!”
There’s so many wonderful Triumph jokes… for me to poop on.

10. Betty White on William Shatner
Not that she’s really ever stopped working in comedy, but the late-late-late-career Betty White career renaissance was sparked by her appearance on the William Shatner roast. Obviously she didn’t write her own material, but the Internet gives Betty White credit for a lot of things other people wrote. But she absolutely nailed her jokes, like “I once had sex with William Shatner. I remember he was up on top of me, huffing and puffing and I’m like ‘You’d better wrap it up, Bill, the roast is going to start any minute.”

11. Patrice O’Neal on Charlie Sheen
Just a few months before he died, roast legend Patrice O’Neal went up at the Sheen roast and essentially threw out his planned material. Instead, he went after the other performers with some realness. He said Seth MacFarlane was jealous of his own cartoon. He called William Shatner an old racist. He claimed Anthony Jeselnik wasn’t important enough for Patrice to learn his last name. He even critiqued the sets by Steve-O and Mike Tyson. Steve-O got his nose broken by Tyson’s fist but it was probably less painful than O’Neal’s set.

12. George Takei on William Shatner
Another aging-celebrity-turned-internet comedy legend was born at the Shatner roast, when George Takei took the stage to roast his not-exactly-friend Shatner. He led with, “My name is George Takei, not Takai, like you’ve insisted on pronouncing it for the last 40 years! Remember: Takei, like in ‘toupee.'” After that, your grandmother’s Facebook page was never the same.

13. Natasha Leggero on James Franco
The roast of James Franco felt like the last gasp of a certain style of mid-2000s comedy: heterosexual white guys calling each other gay, which probably peaked with “This Is The End.” Thankfully, Natasha Leggero was there to bring the roast back to its meanest essence: ripping on someone’s career. She summed him up like this: “James Franco, acting, teaching, directing, writing, producing, photography, soundtracks, editing — is there anything you can do?”

14. Joan Rivers on Joan Rivers
The Queen of Mean had the best joke at her own roast, or at least the best one we can print here. In her closing, Joan Rivers went after Tom Arnold, saying “You were in Betty Ford more times than Gerald was!”

15. Jimmy Kimmel on Flavor Flav
It was early in his late-night hosting career, but Jimmy Kimmel showed off his fearless sense of humor at the 2007 roast of Flavor Flav. After saying that Flav looked like “an open casket memorial for James Brown,” he listed all of Flav’s children and grandchildren, before announcing that Flav was “responsible for more black unemployment than Hurricane Katrina.” It’s 11 years later, and that still feels too soon.

16. Whitney Cummings on David Hasselhoff
Sometimes a comedian will get up at a roast and tell a joke that seemingly changes the trajectory of their career. Such was the case with Whitney Cummings, when she lobbed this howitzer at Pamela Anderson: “Pam, you’ve slept with Bret Michaels, Tommy Lee and Kid Rock. Why don’t you just save yourself some time and drink a vat of Magic Johnson’s blood?” A year after this, Cummings had two sitcoms on the air and was undeniably a star.

17. Joseph Gordon-Levitt on Bruce Willis
Joseph Gordon-Levitt can sing, dance, bike, and wire-walk in movies, so it only figures he also learned how to tell jokes on stage and roast his “Looper” co-star, Bruce Willis. “Bruce, you were so good in ‘The Sixth Sense.’ How did you pretend not to care while a 10-year-old acted circles around you?” However, his best line was saved for Ed Norton: “Who could forget Ed as ‘The Incredible Hulk’? The Avengers franchise, that’s who. Let’s give him a round of applause. I know Mark Ruffalo does every night.”

18. Ireland Baldwin on Alec Baldwin
Alec Baldwin’s roast was full of mediocre jokes about Caitlin Jenner’s transition, but it was the rare roast where the host got off some decent quips. Baldwin said Adam Carolla “hosted a show for car geeks called Top Gear, his favorite episode was finding the most fuel-efficient car to drive into a crowd in Charlottesville.” Chris Redd, perhaps not wanting to slam pseudo-castmate Baldwin, focused on Blake Griffin, saying he looked “like nine different races all working together to make sure you never win a championship.” But Baldwin’s daughter Ireland had the most cutting slam, calling her father “more than some lunatic that loses his temper. He also loses Emmys and Oscars and custody of his firstborn child.”

19. Al Franken on Chevy Chase
Speaking of Al Franken, the former Senator was one of only three “SNL” alums to attend, which he explained because “Chevy’s an arrogant prıck.” He also made fun Chevy’s addiction to “back pills,” and how he once tried to buy an entire kilo of back pills. But the simplest and most cutting joke came when he said “No one laughed harder than Chevy when the town of Chevy Chase, Maryland tried to change its name to Not Funny, Maryland.”

20. Gilbert Gottfried on Hugh Hefner
Though it came as a result of a joke bombing horribly, Gilbert Gottfried delivered the most culturally significant “Roast” moment in 2001. The Hugh Hefner Roast was held two weeks after 9/11, and the audience hated Gottfried when he said he was late because his plane had a stopover at the Empire State Building. In desperation, he started telling the Aristocrats joke, turning the room around and inspiring Paul Provenza and Penn Jillette’s documentary about the world’s filthiest joke.

These are just a few of the memorable moments from the past 20 years of celebrity roasts. The comedy, the insults, and the camaraderie among friends and frenemies make these events a must-watch for fans of comedy and pop culture. Who knows what the next decade of roasts will bring? One thing’s for sure, it will be filled with laughter, shock, and plenty of unforgettable moments.