5 Worst Celebrity Roasts Of All Time, Ranked

There's a fine art to the craft of the celebrity roast. These events are special occasions where actors, musicians, and, yes, future presidents of the United States gather with a dais full of friends and comedians who take them down a notch. It's a rare moment when celebrities feel less like deities are more like a punching bag. It's one of the few times you can say something exceptionally mean to someone's face, and they can't get mad at you ... usually. 

The whole point of a roast is to point out people's foibles, but then a person's set will typically end by saying how much they admire and appreciate the roastee. Of course, there have been times when the roasters went too far. Some stand-up comedians have also gotten in big trouble for offensive jokes at roasts. And then there's the opposite end of the spectrum, where you feel like people are holding back on being as mean as they can be, all for the sake of not hurting someone's feelings. 

From the bland to the brutal, these are the worst celebrity roasts of all time, where you stop enjoying the ribbing (if it's enjoyable at all) and just want it to end for the sake of everyone involved. 

Netflix picked up the roast mantle following Comedy Central's long reign with the format, but if there's one downside to the streaming platform now overseeing the most notable celebrity roasts, it's that they run for three hours. Listen, we love a good ribbing as much as the next media outlet, but at a certain point, you realize how many comedians go to the same well.

In the case of Netflix's "The Greatest Roast of All Time: Tom Brady," everyone really honed in on Brady's divorce from Gisele Bündchen. It's ample roast fodder, but it tends to get repetitive at a certain point. It's one thing making fun of some bad movies someone made, but the jokes got a bit too personal, to the point where Brady will never do another roast due to his kids. After the event, Brady said his children took the 2024 roast pretty hard (even though no jokes came at their expense), and hearing about their response puts a bit of a damper on the whole affair. 

There were some highlights, like Nikki Glaser bringing the house down. But the entire evening got off to an awkward start when the self-appointed Roastmaster General, Jeff Ross, made a massage joke at the expense of Robert Kraft, owner of Brady's main team, the New England Patriots. Kraft was arrested (but later released) for solicitation at a massage parlor, and after the joke, Brady approached Ross and said, "Don't say that s*** again." It's a rare example of a roastee getting offended in real time and feels a bit out of the spirit of celebrity roasts. 

Celebrity roasts are a time-honored institution dating back decades. Sure, they've gotten a bit more profane over the years, but you'd be surprised how vicious people could be even when they aren't constantly dropping swear words. Take, for example, 1999's "N.Y. Friars Club Roast of Jerry Stiller."

Jerry Stiller is a comedy legend. Stiller originally passed on doing "Seinfeld" but eventually became a fan favorite as the father of George Costanza (Jason Alexander). From "Zoolander" to "The King of Queens" to "Heavyweights," Stiller made everything he was in better. There may have been some duds here and there, but he doesn't really have any controversies or attitudes to poke fun of. And that was precisely the problem at his roast. Comedians even noted during the ceremony that there wasn't much about Stiller to make fun of, so they didn't.

Instead, the dais mostly turned their attention to one another, which, admittedly led to some humorous moments. Most notably, Jeff Ross delivered this instant classic burn: "I wouldn't f*** Sandra Bernhard with Bea Arthur's d***," which was accompanied by an absolute death stare from Arthur. On the whole, however, the night was far too tame for what people want out of roasts. Stiller's a great actor and comedian but just doesn't have great roast material. 

Pamela Anderson had the exact opposite problem with her roast that Jerry Stiller had with his. If he had too little to make fun of, she had an overabundance from a slew of very bad movies and TV shows to a string of high-profile romantic relationships gone askew. But there was one topic that became a focal point during the 2005 "Comedy Central Roast of Pamela Anderson" — her infamous leaked sex tape with Tommy Lee.

It was all anyone could talk about during the roast. Naturally, it was a major pop culture event, but in the years since it came out, we've learned more of the true story behind it. Society as a whole has become more sensitive to women getting taken advantage of, and that's precisely what happened with the tape. It was leaked without Anderson's consent, and she never made one dime off it. In hindsight, a night of comedians making fun of a woman who had her autonomy stripped away from her comes across very poorly, even for a roast.

That's not the only thing that's aged poorly from Anderson's roast. Courtney Love was slurring her speech the entire time, clearly intoxicated. And Andy Dick groped Anderson's breasts during the event. Pamela Anderson has been through a long journey from a beer poster model to a '90s TV icon, and her roast was just an excuse to humiliate her even further that doesn't read well today. 

Ever since the Jonas Brothers found fame, they've been mercilessly mocked and ridiculed. Nick Jonas said he had to learn to laugh at a "South Park" episode making fun of the purity rings they touted as young Disney stars to emphasize their faith. It seems that as adults, all of them learned to laugh at themselves after agreeing to appear in the 2021 Netflix special, "Jonas Brothers Family Roast." But we doubt anyone at home was laughing at this exercise in mediocrity. 

Instead of seasoned roasters like Jeff Ross, you have people like Kenan Thompson keeping things pretty tame. The special lacks the biting edge that has come to define roasts. Even their wives got up there to roast their respective husbands, but everything feels too polished. It's like everyone was given a lengthy list of subjects to avoid, so everyone is walking on eggshells. 

On top of that, the roast gets interrupted every so often with odd sketches featuring the brothers. One segment features the siblings doing awful celebrity impressions, with the joke being that they're all really bad at it. But that just means you're watching three famous dudes be terrible at something to try to get laughs. "Jonas Brothers Family Roast" is more cringey than funny, but maybe it's what the brothers needed after being mercilessly ridiculed since they were teenagers.

Roasts are ideally a little mean, but by the end, you know that the roasters truly love and appreciate the person of the hour. Unfortunately that can't be said of 2002's infamous "New York Friars Club Roast of Chevy Chase." 

Chase has a famously abrasive personality, which is responsible for — among other things — the behind-the-scenes drama that led to him getting written off "Community." For his roast, his lackluster attitude meant that very few of his actual friends attended to offer him a good-natured razzing. Instead, he ended up with a bunch of comedians who didn't know him personally and absolutely trashed his career. Chase was reportedly so unhappy that he referred to these up-and-comers as a bunch of nobodies, which probably only fueled the vitriol further. 

Ideally, a roaster finds that sweet balance between being mean for the sake of it and being mean while also being funny. For the Chevy Chase roast, most everyone was just trying to hurt the guest of honor. Even if you despise the actor, it's not particularly fun to watch, which is the whole point of these things. If there's anything to take away from the "N.Y. Friars Club Roast of Chevy Chase," it's that friends are essential to ensure a good, fun event.