Top 10 Most TOXIC Celebrity Roast Jokes of All Time
#10: George Floyd
“The Roast of Kevin Hart” (2026)
In another Netflix roast, Kevin Hart became the latest target of celebrity attacks. He joined the stage with comedians like Sheryl Underwood, Regina Hall, Shane Gillis, and Tony Hinchcliffe. The latter performer stirred up controversy for his joke about George Floyd. You could call the bit racist, or you could just pass it off as a being in poor taste. Some comedians defended Hinchcliffe’s material in the name of free speech, while others like Chelsea Handler took offense. The “Kill Tony” host is known for saying more incendiary lines and certainly lived up to his reputation. No matter which way you look at it, this particular roast will likely be remembered for this joke.
#9: George Takei Hates William Shatner
“Comedy Central Roast of William Shatner” (2006)
When watching this Captain Kirk actor get roasted, you can tell that some of the jokes have a hint of truth about them. William Shatner receives some serious lambasting after George Takei takes the stage. As one of the honoree’s longtime co-stars, the speaker knows the “Star Trek” star as well as anybody in the industry. Takei chooses to go scorched earth on his former colleague rather than playfully rib him. This all culminates in one final line, leaving nothing to the imagination. If you think they’re friends up to that point, you then realize how toxic their relationship actually is.
#8: “The Sixth Sense”
“Comedy Central Roast of Bruce Willis” (2018)
From old co-stars to young comedians, the “Die Hard” star received dozens of jokes about his career, love life, and age. The most startling moment might’ve been when his ex-wife Demi Moore showed up. Willing to dig into their marriage, “The Substance” actress gave a speech that’s full of references to their relationship. One of the best jokes included a nod to Willis’ work in “The Sixth Sense.” The spoiler-filled punchline alludes to the movie’s ghostly protagonist, with Moore more than willing to humiliate her ex-husband. With all of the ridiculous jokes leading up to it, this one seems like the finishing blow.
#7: Stephen Colbert’s Rant
“The N.Y. Friars Club Roast of Chevy Chase” (2002)
Among many infamous roasts, this one seemed to be on the uglier side. Chevy Chase and his bad reputation followed him to this ceremony. As the comedic knives came out, the comedian was caught off guard by the mean material. Stephen Colbert’s segment was especially notable for its sarcasm and an extended rant. In the latter, the “Daily Show” correspondent decided to cut through Chase’s many shortcomings. Colbert’s tone and delivery only make it all the more effective. It’s a remarkable piece of writing, performance, and pointed commentary. If we were the honoree, we likely would’ve surrendered right then and there.
#6: Losing Custody
“Comedy Central Roast of Alec Baldwin” (2019)
This actor definitely earned a reputation for having run-ins with the press and a few other scandals. With this roast, Alec Baldwin was able to face some of his demons and dish out a few comebacks. His daughter Ireland also took the stage to turn the tables on her father. She openly joked about her parents and her dad’s choices in raising her. Throwing in a joke about custody, the younger performer shows that she’s as well equipped to roast as any of the seasoned veterans. Baldwin looks taken aback by all of the personal jabs.
#5: Amy Schumer’s Ryan Dunn Joke
“Comedy Central Roast of Charlie Sheen” (2011)
For the roast of the “Two and a Half Men” star, Amy Schumer made herself known as a no holds barred performer. Her material took aim at Charlie Sheen as well as other attendees like Steve-O. A joke about “Jackass” star Ryan Dunn struck a nerve, making fun of the man’s death while also offering up some commentary about Steve-O’s career. Let’s just say the joke lived on as a controversial snapshot of the event. Cooler heads seem to have prevailed, but the insensitive line wasn’t easy for some people to hear. Schumer did it all in the name of comedy, clearly aware that she’d ruffle more than a few feathers as a result.
#4: Pete Davidson’s Dad
“Comedy Central Roast of Justin Bieber” (2015)
This roast caught Justin Bieber after he became something of a toxic piece of pop culture. Willing to laugh at himself, the singer endured a slew of jokes at his expense. Pete Davidson and then took the microphone, wading in murky waters as he brought up his father. The comedian’s dad died on 9/11 and his signature joke made light of that situation. While riffing about Bieber’s own parental situation, Davidson unleashed a line that was as harsh as it was darkly funny. Coming from anybody else, you’d almost want to stop the roast dead in its tracks. The comic knew what he was doing as he turned up the temperature of a good-natured event.
#3: Jeff Ross’ Robert Kraft Joke
“The Roast of Tom Brady” (2024)
Being one of the most decorated NFL athletes, Tom Brady earned both friends and enemies over the last few decades. His Netflix roast brought out former players, teammates, and comedians like Jeff Ross. The Roastmaster General offered up some incredible takedowns and even a jab at Patriots owner Robert Kraft. Joking about the businessman’s scandal, Ross actually drew the ire of Brady. The comedian received an earful from the quarterback during the performance. It was almost as if that line made the football great more angry than anything else. One thing is for sure, you don’t joke about somebody’s former boss on a large streaming platform.
#2: Trayvon Martin
“Comedy Central Roast of Rob Lowe” (2016)
During the roast of this Brat Pack member, many of the most volatile jokes were directed at Ann Coulter. She was the odd woman out among more esteemed actors and veteran comedians. David Spade went after the author and her controversial views on race and politics. The result was a reference to the death of Trayvon Martin, earning some wild reactions from the crowd. This one rode the line between being offensive and being an edgy takedown of Coulter. Spade uttered the joke off with pure confidence, letting the audience know he was up for almost anything.
#1: Gilbert Gottfried’s 9/11 Joke
“The N.Y. Friars Club Roast of Hugh Hefner” (2001)
This roast came a short time after September 11th, 2001 and tested the concept of “too soon.” Gilbert Gottfried joined an illustrious list of roasters, creating a moment that went down in comedy history. The comedian made a joke about the Empire State Building that alluded to 9/11. With a mixed reaction, Gottfried decided to double down with an even crazier choice. You can judge whether or not the line was tasteless, but that’s not even counting his interpretation of The Aristocrats. The comic went on a graphic rant that destroys the limits of good taste. Between joking about then-recent tragedies and street jokes, this speaker went out of his way to test the audience.
Did we forget another killer line from a roast? Let us know in the comments below.
