The Funniest and Most Vicious Comedy Central Roast Speeches

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We’ve reached the “publicly begging people to show up” phase of planning for Justin Bieber’s March 30th roast on Comedy Central; yesterday, the noted Photoshop template took to social media to ask Seth Rogen, whose low estimation of Bieber is well known, to tear him a new one on national television. As the hype surrounding the Kevin Hart-hosted event (Kate McKinnon, presumably, didn’t have time for the gig given her SNL schedule), we’ve rounded up some of the best appearances from the network’s 17-year tradition of having comedians puncture stars’ egos, and each other’s, on camera.

Norm MacDonald on Bob Saget

The defining trait of a roast is its participants’ attempt to one-up each other with disgusting, insensitive, and generally tasteless zingers. Which means the most shocking approach of all might be Norm MacDonald’s 2008 decision to read off a list of toothless, clichéd one-liners. (He later told Marc Maron that he’s not a fan of roasts in general and cribbed the digs from a retirement-party joke book his dad gave him when McDonald started doing comedy.) Watching the audience slowly realize what’s going on, and the comedians onstage lose it, is the highlight of this decidedly trollish set.

Andy Samberg on James Franco

Continuing with the postmodern roasting theme, Samberg delivered a two-minute tirade that was more about his own character’s empty shell of a life than his target’s sore spots. Aziz Ansari has a unique perspective on the American experience, Natasha Leggero might someday know the wonder of giving life, and Jonah Hill is really nice about kicking unwanted guests out of dinner parties — zing! The set ends with a shout-out to God, whose omnipresent love makes Him the biggest sucker of all.

Whitney Cummings on Joan Rivers

Almost all the potshots at Cummings during Joan Rivers’ 2009 event focused on her status as a relative unknown (this was, of course, pre-Whitney). But her vicious set — including the unforgettable description of Tom Arnold and Roseanne Barr as “John and Kate plus an eight ball” and a comparison of Joan Rivers’ face to “what Ivanka Trump would look like if she were dating Chris Brown” — proved she could hold her own against roast standbys like Jeff Ross and Greg Giraldo.

Anthony Jeselnik on Charlie Sheen

Jeselnik’s entire act is based on sticking with self-contained jokes in the age of the extended, conversational bit, so roasts are sort of his natural habitat. He’s made three appearances — skewering Roseanne Barr, Donald Trump, and here, Charlie Sheen — but Sheen’s is a personal favorite. There’s a nice ad-libbed exchange with Patrice O’Neal, a good two minutes spent on Mike Tyson alone (“Mike Tyson. That’s the whole joke”), and the spot-on assertion that Sheen only has a career “because God hates Michael J. Fox.”

Gilbert Gottfried on Hugh Hefner

Before Comedy Central created its own event, it broadcast the annual Friars Club Roast. Hugh Hefner’s turn in the hot seat concluded with a set from Gilbert Gottfried that’s notable for its masterful diffusion of the tension surrounding a particularly awful (and unfunny) rape joke from Ice-T and Gottfried’s personal spin on “The Aristocrats,” which got cut from broadcast but lives on in the 2005 documentary.

Greg Giraldo on Larry the Cable Guy

A roast regular until his death from an overdose in 2010, Giraldo’s hits on his fellow comedians from this 2009 show are mostly forgettable until he starts on the man of the hour. There’s not even a joke buried in his call-out of Larry’s catering to the lowest common denominator of the racist, homophobic American public, and the fury in his voice when he screams “HOW THE FUCK ARE YOU SO POPULAR?!” doesn’t exactly sound feigned.

Patrice O’Neal on Charlie Sheen

O’Neal ditches the traditional roast rhythm (and his own notes) in favor of a less formal approach here. There’s not even a punchline to telling William Shatner he comes off like a racist old man, but O’Neal sells his honesty anyway. And who can’t respect someone for refusing to learn any more “shitty last names” after Galifianakis?

Bill Hader on James Franco

As Herb Welch fans can attest, Bill Hader has the grumpy old man character on lock, and it was a pleasant surprise to see him show up as the tracksuit-clad “President of Hollywood” in lieu of his affable self. It’s hard to see the real Hader going after Seth Rogen’s unlikely leading-man status (Hollywood put Rogen on a poster and told America to “deal with it”) or Jonah Hill’s near-identical schtick — a welcome reprieve from the evening’s fat jokes. His pronunciation of “Samboig” is also one for the ages.

Betty White on William Shatner

Everyone loves Betty White, a fact that she shamelessly exploits to deliver one-liner after one-liner. Being America’s Raunchy Grandma has its benefits, including the ability to get away with saying things like, “Everyone knows Shatner’s nuts… but George [Takei] has actually tasted ’em!” Never change, Betty.

Snoop Dogg on Donald Trump

Yeah, they let Snoop Dogg do one of these. (Two, actually, but his 2007 take on Flavor Flav was delivered as a rap; this was his first venture into the traditional monologue format.) Observe the results.