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Every Comedy Central Roast, From Worst to Best

From Flavor Flav to Larry the Cable Guy, we rank every one of the network’s insult-athons

Flavor Flav and Charlie Sheen

Flavor Flav and Charlie Sheen

Jason Merritt/FilmMagic/Getty; Christopher Polk/Getty

It's an age-old, and admittedly odd, tradition: A famous person gathers together a room full of friends, celebrity fans and some of the funniest stand-up comics working today — and then invites them to say the most horrible things imaginable about him or her in front of a crowded room and TV cameras. The history of professional roasts dates back to the Fifties, when the private organization known as the Friars Club gave its male members — women were not allowed in until 1988 — the chance to put on tuxedos and take low-blow pot shots at other comedians. It was all in the name of affectionate (if incredibly aggressive) fun, with the Friars' friendly-fire tradition eventually making its way to cable in 1998. Then Comedy Central began producing their own take-no-prisoners celebrations in 2003, and the channel has shouldered the responsibility of broadcasting cultural icons getting ripped to shreds ever since.

As Justin Bieber prepares to join the ranks of the roasted on March 14th (the network will air the event on March 30th), we look back at the complete roster of Comedy Central's insult-athons, ranked from worst to best. Warning: None of these are for the faint of heart or easily offended. All of them, however, feature comics taking the gloves off and hitting way below the belt. With friends like these….

Flavor Flav and Charlie Sheen

Jason Merritt/FilmMagic/Getty; Christopher Polk/Getty

4

Donald Trump

While its honoree comes across as kind of a joyless prick, and the show is without the reliable Greg Giraldo — who passed away the previous fall — the Trump roast features some of the most consistently on-point performances of any of Comedy Central celebratory cutdowns. Lisa Lampanelli and Whitney Cummings arrive with knives out, a bit in which Marlee Matlin's interpreter gets replaced by a politicized Gilbert Gottfried works brilliantly, and Snoop Dogg stays alert enough to make his material pop. (Even Mike "The Situation" Sorrentino's notoriously disastrous set is fascinating for comedic rubberneckers.) The smirking Anthony Jeselnik probably sums up Trump best: "The only difference between you and Michael Douglas from Wall Street is nobody's going to be sad when you get cancer." Boom.

Flavor Flav and Charlie Sheen

Jason Merritt/FilmMagic/Getty; Christopher Polk/Getty

3

Pam Anderson

Chatty, silly and slightly anarchic due to the presence of a visibly intoxicated Courtney Love smeared across the back of every frame, this fun, raucous 2005 affair finds Anderson still in the public consciousness enough to be a good target. Nick DiPaolo assaults everyone, Bea Arthur reads tales of anal sex and Sarah Silverman praises the animal-loving Anderson's "good work with the one-eyed trouser snake." Jeff Ross' joke about Love — "How is it possible Kurt Cobain looks better than Courtney Love?" — draws gasps from the audience. But the comedian is such a consummate pro that he not only wins the crowd back, Love even simulates fellatio on the man later during the ceremony. (She went into rehab shortly after the shoot.) For anyone needing proof that anything goes at these events, this is Exhibit A.

Flavor Flav and Charlie Sheen

Jason Merritt/FilmMagic/Getty; Christopher Polk/Getty

2

Hugh Hefner

Sure, going after Hef feels like shooting fish in a barrel. But in the world of roasts, easy targets can inspire comedians to transform overworked premises into barbs with perfect accuracy. Take this summation from roastmaster Jimmy Kimmel: "What can you say about Hef that hasn't already been said by 1,000 young women with his cock in their mouths?" There's also a kind of easter egg in this roast, material that was cut from the final broadcast but was highlighted by 2005 documentary The Aristocrats, that pushes it to legendary status. The roast itself was filmed in late September 2001, and Gilbert Gottfried made jokes about the World Trade Center attacks that were too close to home. Rather than give up, Gottfried redoubled his efforts in telling the well-known dirty joke known as "The Aristocrats," and won only the audience's love with a wild torrent of filth. In one fell swoop, the diminutive comic led the room through some of the most cathartic, you-have-permission-to-laugh-again howling you've ever heard. It's one for the ages.

Flavor Flav and Charlie Sheen

Jason Merritt/FilmMagic/Getty; Christopher Polk/Getty

1

Charlie Sheen

Roasts succeed when a willing target with a thick skin has skeletons that refuse to languish in the closet; in this regard, raving Vatican assassin Charlie Sheen, circa 2011, is perfect. Thankfully, the dais — an excellent mix of professionals, funny weirdos and unpredictable personalities like Mike Tyson — know how to exploit even an obvious mark. "How do you roast a meltdown?" asks Jeff Ross, clad in Muammar Gaddafi getup. Sheen beams while taking his lumps from these strangers, a madman thrilled by a downfall of his own design. And while there are many stand-out performances, this roast celebrates the emergence of one big talent while immortalizing another. Amy Schumer's sly, assured first roast appearance seduces and stuns the crowd; her line "You're like Bruce Willis: You were big in the Eighties and now your old slot's being filled by Ashton Kutcher," is one of the best ever uttered during a roast, period. And Patrice O'Neal, in what would be his final TV appearance, ditches his notes at the podium. Slowly, methodically, the comedian picks off his fellow roasters with a befuddlement and frustration so honest that it blows everyone away. It's ruthless, earth-scorching and hilarious — exactly what these events should be.