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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

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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….

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18

Denis Leary

With a line-up primarily made up of straight, white guys, the Leary roast hearkens back to the boys' club feeling of the Friars' events — minus the elderly Jews. While friends and Rescue Me costars like Adam Ferrara and Lenny Clarke take pot shots, Leary perches on a barstool next to Kiefer Sutherland and Liz Hurley because, uh, he knows people. When highlights include a swearing priest, Christopher Walken's taped appearance and a ridiculous bit about Leary's joke-slinging Irish wolfhound, it's easy to wish that a seasoned MVP like the late Greg Giraldo hadn't riled Leary during their Tough Crowd With Colin Quinn appearance (the two almost came to blows) ; this one desperately needed a ringer.

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17

James Franco

"I can't tell if this is a dais or the line to suck Judd Apatow's balls," Sarah Silverman quipped during this recent roasts; as for the event, it felt like a press release for itself. The handsome, young, multi-hyphenate Franco asks friends to josh him about phoning in his Oscar-hosting gig. Nick Kroll and Jonah Hill give it their best (the former gets the dig of the night: "Jonah, a lot of people are going to touch on your weight tonight, but not enough people are going to talk about what an asshole you've become"). Bill Hader is fun as the "President of Hollywood," while Andy Samberg makes an A-for-effort attempt at mocking the practice of roasts. Professionals like Silverman, Jeff Ross and Natasha Leggero know what they're doing, but roastmaster Seth Rogen sums it up best when he rhetorically asks. "Why are we here, James?" Why, indeed.

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16

Jerry Stiller

The biggest problem in the Jerry Stiller roast is…well, Jerry Stiller. The genial actor and comic is simply too nice to lay into with the sort of cuts-to-the-bone remarks required for these evenings, and you can tell everyone's having a hard time finding a good place to slip the knife in. Some of the old guard from the Friars Club are still around to deliver their schtick, and Ben Stiller gets in a few absent father digs, but it's generally pretty dull. The only good thing about Sandra Bernhard's highly uncomfortable rendition of Heart's "Magic Man" is Jeff Ross's jarring follow-up: "Sandra Bernhard, I wouldn't fuck you with Bea Arthur's dick." The glare that Arthur gives the roastmaster after that oft-quoted one-liner is pure comic gold.

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15

Drew Carey

One of the few Friars Club productions to be broadcast on Comedy Central, this special features a number of older, revered comedians whom very few young viewers would know on sight: Kip Addota, Dick Capri, Alan King. It's also got a hammy, old-fashioned borscht-belt sensibility, and not even younger all-stars like Margaret Cho can't stave off a certain sense of mustiness. Thankfully, Dave Attell livens things up by working blue when talking about "Mr. Las Vegas TV Show" ("We all know what your favorite song is, and that's your balls slapping against a hooker's ass — it's got a great beat and it always makes you hungry"), and Jeff Ross makes his first roast appearance here, dropping zingers like, "Drew Carey is to comedy as Mariah Carey is to…comedy."

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14

Jeff Foxworthy

Given that the clean-cut father figure of the Blue Collar Comedy Tour is the guest of honor, it's not surprising that this particular roast is a highly populist affair — you get the comedy stylings of Bill Engvall, Larry the Cable Guy, Anna Nicole Smith and a George W. Bush impersonator, all backed by the wanky guitar riffs of G.E. Smith. Foxworthy comes off like a remarkably likable guy, but as he's spent a lifetime taking himself down with redneck jokes, all that's left for veterans of Colin Quinn's old Tough Crowd crew like Greg Giraldo and Nick DiPaolo to do is knock the man's pedophile mustache and kill time. Occasionally, you get a well-crafted quip like Quinn's crack about the salt-of-the-earth stand-up being "the hillbilly metrosexual judge in a child beauty pageant." But we'll put it this way: You know you're a die-hard Foxworthy fan if you can make it through the whole thing without reaching for the remote.

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13

Chevy Chase

Famously ruffled by the failure of his high-profile friends to show up — and by being shat on by a bunch of B-list comics he does not know — honoree Chevy Chase did not have a good time at his roast to say the least. It's excruciating to observe the SNL veteran maintain a forced smirk under his dark glasses for close to an hour, though there are several surprisingly good performances tucked away in the dour night: Todd Barry's low-key smarts, Marc Maron's exasperated ranting and Stephen Colbert's mocking grandiloquence all play well. But no, it's not fun to watch Chase stand up and say, "That hurt."

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12

David Hasselhoff

When this roast was filmed in 2010, the beloved but deflated David Hasselhoff was being remembered for a pathetic online video in which he drunkenly ate a hamburger while his kids begged him to stop drinking. The set is Baywatch-themed. George Hamilton, Hulk Hogan and Jerry Springer are on the dais. Greg Giraldo is excellent per usual, and Jeff Ross, Lisa Lampanelli, Whitney Cummings and Gilbert Gottfried all get a few good jabs in. (Cummings FTW: "When I tried to buy your music on Amazon.com, it said 'users who bought this item also bought…a shotgun.'") Hoff is a good sport throughout, but there's hardly a reason for this to happen. As Pamela Anderson tells him, "When they roasted me, I was relevant."

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11

Bob Saget

Yes, Comedy Central roasted a man best known as Danny Tanner on Full House and the host of America's Funniest Home Videos — in 2008. To be fair, Saget is a stand-up comic and a notably dirty one, but let's say this isn't an incredibly timely choice for the national viewing audience. And though the former sitcom star looks a little mystified about being there, he's more than willing to let chums including John Stamos take him down. Stylistically, the peanut gallery is all over the place — from Jeff Garlin's breezniness to Gilbert Gottfried's relentlessness — but the best, and most surprising, set comes from none other than Norm MacDonald. His beyond awkward dad jokes were an honest response to a producer's suggestion that he be shocking; by making a full 180-degree turn to ultra-cheesiness ("Bob has a beautiful face, like a flower. Yeah, cauli-flower!"), he stole the show.

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10

Roseanne Barr

For a groundbreaking sitcom star and comedienne who's paid her dues and offered no shortage of ammunition for a roast, it's shocking how unremarkable how Barr's roast is. For every comic like Amy Schumer who beautifully works the room (regarding the lineup, she quips that it's "a real who's-who of an Activia commercial so far"), whimsical, less-than-stellar picks such as Carrie Fisher and Ellen Barkin have a tendency to slow things to a halt. Give Gilbert Gottfried credit for the level of commitment in his hateful comments and Anthony Jeselnik turns in another solid set of dark, snide and biting jokes. (His version of a fat joke: "Here's something positive: You had gastric bypass surgery in 1988, and then you beat it.") But it's Barr who ends up hitting the bullseye, taking aim at her ex-husband Tom Arnold. "He was very funny," she says, "but Jesus Christ, how many fucking jobs do I have to get for that guy?"

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9

Rob Reiner

In Reiner's roast, you can feel the smoke-filled, chummy back room of Friars Club slowing having its furniture rearranged by a network seeking viewership. Old-guard regulars like Freddy Roman and Abe Vigoda are there, but so are younger outsiders, like Kevin Pollak and walking punchline Vanilla Ice. Reiner is a wonderfully jovial target, egging on attackers who jab him about marriage to Penny Marshall, his weight, and then his weight again. Robert Smigel's appearance as Triumph the Insult Comic Dog is the best example of playing both sides against the middle, mocking the age of the club's members and its rituals while readily participating in them: "Have you ever seen Alan King naked in the steam room? Normally I have to eat grass if I want to puke."

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8

Flavor Flav

Though roastmaster Katt Williams decried what he'd later call the "crispity crackily crunchy coon" jokes in the 2007 broadcast, the roast holds up despite the plethora of jabs about Flav's skin tone. (As Jeff Ross crudely puts it: "The fact that Flav is black is like the fifth thing that's wrong with him.") Still fresh from the sloppy, unfortunate reality mess Flavor of Love, and wearing his signature clock as well as a gold crown, the Public Enemy hype man looks to be having the time of his life, even cackling at Carrot Top's prop comedy. The usual suspects — Ross, Lampanelli, Giraldo — kill, of course, while the seemingly out-of-place Patton Oswalt more than holds his own. ("Thank you, pimp in a thimble!")

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7

Joan Rivers

Always game to work, comic icon Rivers patiently presides over a guest list described by Greg Giraldo as "a couple of trolls, a fairy and a giant going after a sunken-eyed monster obsessed with jewelry. It's like Lord of the Rings." The performers aren't exactly Rivers' crowd, and there are unexpected characters working the podium such as Robin Quivers, but it actually gels; Whitney Cummings' performance was so assured (regarding the prevalence of elderly comics onstage, she remarked "I don't know if I should be telling jokes or calling out bingo numbers"), it helped launch her into the Hollywood consciousness. And unlike most of the other honorees, Rivers knows how to close: After slapping roastmaster Kathy Griffin, she delivers sharp material and gives herself a big, self-congratulatory finish that restores balance after the verbal beatdown she endured. There's a reason she's referred to as a legend.

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6

Larry the Cable Guy

"How the fuck are you so popular!?" Greg Giraldo fumes at the cutoff-shirt-and-ballcap-clad character on the throne before him. No answer is forthcoming, but the rest of the roast proves that while Larry and the other Blue Collar guys play directly to their audience's sensibilities, they can take a joke. Forget the predictably bland sets from a host of personalities including Toby Keith and Maureen McCormick; concentrate instead on the all-around bizarre appearance of a spacey Gary Busey, which ping-pongs between a deader-than-deadpan monotone and angry outbursts. With vigorous sets from Giraldo, Ross, and Nick DiPaolo, and Lisa Lampanelli on host duty, the majority of the show sings along at a rapid clip. To paraphrase the man of the hour, it gets it done.

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5

William Shatner

Captain James T. Kirk casts a long shadow here, but Shatner has enough strange hobbies — e.g. spoken word, being a weirdo in commercials — to keep things interesting. George Takei and Nichelle Nichols hold it down for the crew of the Enterprise; the rest of the dais of comics and nerd-comics — give it up for Patton Oswalt — toy with Shatner's ego while avoiding Andy Dick, who manages to lick the faces of nearly everyone onstage. This night may have also been the first time people got excited about perky Betty White talking dirty: "We all know Shatner's nuts, but George has actually tasted them!" No one boldly goes where no man has gone before in terms of ribbing Bill for his lack of acting chops, but with this much comic force kicking into warp speed, they don't need to.

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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.

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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.

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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.

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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.