Comedy Central has been roasting all sorts of different celebrities since 1998. The roasts, which usually consist of an hour and a half special of making fun of every aspect of a celebrity’s life, have featured celebrities like Pamela Anderson, Drew Carey and Hugh Hefner. Some of these celebrities let their roasters make fun of every aspect of their lives. As expected, this led to some harsh jokes directed at the roasted celebrity. Others, decided to put limits on the subjects that roasters were allowed to use. For example, Pamela Anderson didn’t want anyone to joke about her Hepatitis C infection and Joan Rivers refused to let anyone joke about her daughter. Even though these celebrities tried to limit a certain amount of verbal pain, the roasters still managed to hit them where it hurt. So for your entertainment, below is a list of thirteen of the most brutal roasts that comedy central has ever aired. All of these roasts hit the roastee below the belt and made audiences say, “I can’t believe they just said that.”
In case you are a Comedy Central Roast fan, the next roastee will be none other than Justin Bieber. The roast is scheduled to air in March 2015.
13. Jeff Foxworthy
The roast of Jeff Foxworthy took place in 2003 and featured Jeff Garlin as the roastmaster and Jim Breuer, Michael J. Fox, Dane Cook and Gilbert Gottfried as the roasters. The funniest jokes from the roasts weren’t actually aimed at Foxworthy. Instead, all of the roasters took turns roasting each other in the most brutal way possible. One of the highlights of the night came from Steve Bridges, who spent the entirety of the roast impersonating George W. Bush. The comedian’s impersonation of George W. Bush was spot on, which made the jokes that were hurled at the former President’s expense, all the more hilarious.
Here’s a clip of Lisa Lampanelli doing what she does best at that very roast:
12. Larry the Cable Guy
The roast of Larry the Cable guy marked the first time that a roastmaster became the roastee. Larry the Cable Guy’s roasters included Jeff Foxworthy, Toby Keith and Jeffrey Ross, among others. Some of the best jokes from the night include Jeff Foxworthy’s joke, “I find the best way to enjoy one of Larry’s movies is never put it in the DVD player,” Lisa Lampanelli’s joke, “Larry the Cable guy has everything: sleeveless shirts, stupid catchphrases. He’s Mr. T without the acting chops,” and Greg Giraldo’s joke that got straight to the point when Giraldo asked Larry the Cable Guy, “How the f***k are you so popular?”.
11. Flavor Flav
The roast of Flavor Flav took place in 2007 and featured roasters like Ice T, Jimmy Kimmel, Snoop Dog and Greg Giraldo. One of the most shocking moments of the night came when Greg Giraldo compared Flavor Flav to the ex-Ugandan dictator Idi Amin, after coming off a five year binge on crack. Another joke aimed at Flavor Flav’s skinny stature came when Jeff Ross said, “starving children send YOU 50 cents a day,” and of course there’s the joke where Jeff Ross asked the very important question, “This roast is impossible, how do you embarrass a crackhead who wears a Viking helmet.”
10. Chevy Chase
The roast of Chevy Chase aired in 2002 and featured Paul Shaffer as the roastmaster. During the roast, Chevy Chase seemed to be in a hilariously bad mood because none of his SNL friends had shown up. As a result, the show was all sorts of awkward. However, even though Chase was in a foul mood, that didn’t stop his roasters from delivering some brutal jokes at his expense. Chase’s roasters made fun of everything from his age and his supposed lack of talent. In a particularly brutal joke, Greg Giraldo pointed to Chase and said, “living proof that you could actually snort the funniness right out of yourself.”
Stephen Colbert’s performance was also praised for its original approach to roasting Chevy, as seen in this clip (at 34min30sec)
9. William Shatner
The roast of William Shatner aired in 2006 and featured Jason Alexander as the roast master, and Andy Dick, Farrah Fawcett and Greg Giraldo as the roasters. The tagline for the show was, “The Shat hits the fan,” which was a pretty appropriate tagline for Shatner’s roast. Roasters poked fun at Shatner’s weight, “You have boldly let yourself go,” and of course, other jokes that included black jokes, Jew jokes, and Japanese jokes. The entire show was basically a chance to see which comedian could be ruder, more scandalous and of course, who could say the most hurtful things about William Shatner.
8. Hugh Hefner
The roast of Hugh Hefner aired in 2001 and featured Jimmy Kimmel as the roastmaster. The roast took place just weeks after the 9/11 attack and marks the first time that someone told a 9/11 joke, which in retrospect might have been a bit too soon. Even with the poorly timed joke, the Hugh Hefner roast is considered to be one of the best roasts of all time. Some of the jokes took aim at his many girlfriends, his age and crude jokes about his sex life with his young girlfriends. Through it all, Hefner was a good sport who took everything in stride.
7. Bob Saget
The roast of Bob Saget aired in 2008 and featured John Stamos as the roastmaster and Greg Giraldo, Gilbert Gottfried and Jeff Ross as the roasters. During the show, Norm MacDonald said a bunch of cheesy, poorly delivered jokes from a book called Jokes for Retirement Parties. Eventually the audience caught on to what he was trying to do and joined in on the fun. Some more brutal jokes included sexual jokes about the Olsen twins, most of which were edited out of the show. In a later interview Saget said that he believed the jokes about the Olsen twins had taken things a bit too far.
6. Donald Trump
The roast of Donald Trump was raunchy and offensive, so it was basically everything a roast should be. The roast took place in 2011 and featured Seth MacFarlane as the roastmaster and roasters such as Whitney Cummings, Lisa Lampanelli and Jeffrey Ross. Some of the raunchiest jokes of the night came from comedians Whitney Cummings and Seth MacFarlene. Cummings joked, “You got Melania a huge, 12-carat diamond engagement ring. You should not have gotten her a diamond. Now she knows what hard is supposed to feel like. On the other hand, MacFarlene roasted Trump with sex jokes. This roast was also the debut for comedian Anthony Jeselnik and his blend of dark crude humour
5. Roseanne Barr
The roast of Roseanne Barr took place in 2012 and featured Jane Lynch as the roastmaster and roasters such as Carrie Fisher, Wayne Brady and even Roseanne’s ex-husband, Tom Arnold. Throughout the night, there were many jokes aimed at Barr’s weight and age. One of the harshest jokes aimed at Barr’s weight came from the roastmaster herself. Lynch joked, “Roseanne, it’s not your fault you were attracted to Tom. You thought with all that white powder on his upper lip, there must have been a donut somewhere.” Another joke that was aimed at roaster Carrie Fisher goes as follows, “Carrie is here to put Roseanne’s weight and drug problems into perspective.”
4. Joan Rivers
The roast of the late Joan Rivers took place in 2009 and featured comedians such as Kathy Griffin, Mario Cantone, Greg Giraldo and Jeffrey Ross. As per usual, most of the jokes were pretty racy. Some of the best jokes included Griffin’s joke, “Joan is not an Orthodox Jew, but men still f**k her through a sheet so they don’t have to look at her face,” Giraldo’s joke, “you used to look your age; now, you don’t even look your species,” and Robin Quivers’ joke, “your face doesn’t move. I can’t believe they haven’t hired you to host New Year’s Rockin Eve.”
3. Pamela Anderson
The roast of Pamela Anderson took place in 2005 and featured roasters Jimmy Kimmel, Courtney Love, Adam Corolla, Sarah Silverman and more. At center stage, Anderson wore a see-through black top with no bra, but that was definitely not the most scandalous event of the night. Some of the harshest jokes of the night were aimed at Courtney Love, who was acting pretty oddly throughout the show. During the show, Jeffrey Ross joked, “How is it possible that Courtney Love looks worse than Kurt Cobain?” To which Love slurred back, “I’ve been sober for over a year.” Finally, Jimmy Kimmel shot back by saying, “If you’re not on drugs, you’ve got problems.”
2. David Hasselhoff
The roast of David Hasselhoff aired in 2010 and featured comedians such as Lisa Lampanelli, Whitney Cummings, Greg Giraldo and Jeffrey Ross. Some of the best jokes of the night came from Pamela Anderson who said, “Oh, David. I know you’re in pain. I know what you’re going through. Except when they roasted me, I was relevant,” Whitney Cummings who said, “David Hasselhoff, George Hamilton, Hulk Hogan…I think if we’ve learned anything tonight, it’s that self-tanner causes you to fail in the entertainment business,” and Greg Giraldo who joked, “You had a car that started when you talked into it, now you have a car that won’t start when you blow into it.”
1. Charlie Sheen
The roast of Charlie Sheen took place right after Sheen had a very public breakdown, so there was plenty to poke fun at. The show featured Amy Schumer, Jeffrey Ross and Mike Tyson, among others as the roasters. Some of the harshest jokes of the night included one by Seth MacFarlane who said, “Honestly, Charlie, I never thought I would live to see the night that you would live to see this night,” a joke by Kate Walsh who said, “You know, it’s amazing. Despite all those years of abusing your lungs, your kidneys, your liver, the only thing you’ve had removed is your kids,” and a joke by Jeffrey Ross who roasted Sheen by saying, “Instead of getting his life together, Charlie went out on a national comedy tour where every night you walked out on stage and told the audience you were a warlock from Mars. Maybe you are, but I’ll tell you what you’re not: a comedian from Earth.”