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The 20 Best Comedy Central Roast Sets Ever

Photo-Illustration: Maya Robinson/Vulture and Photos by Getty Images

A different version of this post ran on August 28, 2013, before the James Franco Roast. We have updated it ahead of this weekend’s Bruce Willis Roast.

Though you have to imagine people have gathered around to tribute their friends by insulting them ever since Oog retired from the ol’ Moving Rocks From One Hill to Another Hill company back in Paleolithic times, the first time people dressed up nicely to do so while eating overcooked chicken breast was probably at the Friars Club in 1907. The name “roast” would come later (1949), but the tradition was started. And it continues still to this day — most publicly in the form of Comedy Central’s every-so-often roasts of famous people, which the network has been airing for 20 years now, first with the Friars and then without.

But what makes a good roast? Of course it’s the jokes. It is a joke-writer’s medium. But, like everything, it’s also about the comedian’s point of view and how they play off the subject. The best make a decades-old style their own. So with the Bruce Willis roast airing this weekend, we went back through all the previous affairs and found the absolute funniest sets, from Jeff Ross to Snoop Dogg, Sarah Silverman to Anthony Jeselnik, Norm MacDonald to Andy Samberg. (We limited the list to one per comedian so the dang thing wouldn’t be all Greg Giraldo.) Enjoy, and remember: They only roast the ones they love … and Donald Trump.

Roaster: Jeff Ross
Roast: Drew Carey (1998)
If you want to know why Jeff Ross is at all of these roasts, watch his set at the first one, which showcases Ross’s specific blend of contemporized old-school (read: Jewish) joke telling. It’s great to watch Ross with the energy of a comic trying to prove himself among a much older milieu.

Roaster: Drew Carey
Roast: Hugh Hefner (2001)
Despite being taped only a couple weeks after 9/11 (or maybe because of its cathartic timing), Hefner’s roast was easily one of the two or three best ever. Hefner was a perfect victim: a likeable good sport with lots of things to target. In a night of people making old jokes, Carey’s were the best.

Note: Drew Carey’s set begins at 34:45.

Roaster: Sarah Silverman
Roast: Hugh Hefner (2001)
Similarly, in a night of people making fun of the bunnies, Silverman stood out with the freshest and funniest angle on them. Her style fits so nicely with the roast; she also killed it at the Franco Roast.

Note: Sarah Silverman’s set begins at 28:30.

Roaster: Todd Barry
Roast: Chevy Chase (2002)
The Chevy Chase roast was famously awkward. Chase was in a terrible mood and a poor sport because most of his SNL peers didn’t show up. One of the few bright spots was Todd Barry. Not really a tough, insult comic, Barry used his bone-dry, sardonic style to make fun of how easy it is to make fun of Chevy.

Note: Todd Barry’s set begins at 15:10.

Roaster: Patton Oswalt
Roast: Flavor Flav (2007)
Oswalt is also not your typical roaster, but at the Flavor Flav roast he effectively adapted his alternative, verbose style to make fun of people. Oswalt proves no one can be cutting like a nerd can. He even squeezes in a Star Wars reference!

Roaster: Norm MacDonald
Roast: Bob Saget (2008)
MacDonald’s infamous roast set is a good barometer for people’s senses of humor. For some, it’s a bunch of unfunny, cheesy jokes. (They’re wrong.) To others, it’s an anti-comedy master class. He later revealed his set was a response to a producer telling him to “just try to be shocking!” He realized that nothing would be more shocking than poorly delivering old jokes he got out of a book his dad gave him called Jokes for Retirement Parties. It’s fun to hear the audience slowly catch on to what is happening.

Roaster: Greg Giraldo
Roast: Larry the Cable Guy (2009)
Picking Giraldo’s best set of the eight roasts he appeared in is incredibly difficult. Simply, he was the best, most consistent roaster. His career never went as high as it deserved to (and was sadly cut short by his 2010 overdose). Something about Larry the Cable Guy’s massive success just made Giraldo see red. You can tell Giraldo really enjoys this one.

Roaster: Nick DiPaolo
Roast: Larry the Cable Guy (2009)
Say what you will about Larry the Cable Guy, but he was easily the best sport of all – the meaner the thing said about him, the more he laughed. And DiPaolo particularly killed it. He had done a few roasts before this one, and his jokes were the best mix of harsh and clever.

Roaster: Whitney Cummings
Roast: Joan Rivers (2009)
Recently, a good roast set has helped comedians break out. This was the case with Cummings’s appearance at the Rivers roast, when she was an unknown. You can see why. These days, people like to make fun of Cummings, but this set demands she not be underestimated.

Roaster: Gilbert Gottfried
Roast: David Hasselhoff (2010)
There have so many Gottfried classics that it is hard to single out one. But the Hasselhoff event was his best in terms of mixing straight jokes with pushing surreal premises as far as possible. Also, it displays how brilliant he is at subverting classic jokey jokes.

Roaster: Snoop Dogg
Roast: Donald Trump (2011)
It’s nice to have non-comics at the roasts. They shake things up and make it so the shows aren’t exclusively an inside-baseball game where a bunch of comics make fun of each other. However, very rarely are they genuinely funny; even if they do have professional comics writing their jokes, their timing tends to be slightly off. Snoop Dogg, who also appeared on the Flava Flav roast, is the exception. He’s weirdly great at these. Even if he had someone write his jokes, he picked some good ones and sold them.

Roaster: Marlee Matlin
Roast: Donald Trump (2011)
Like political jokes, sketchlike bits don’t usually go over that well at the roasts, but this one definitely does. It involves Gilbert Gottfried acting as Matlin’s signer, mixing his abrasive absurdity with the vaudevillian simplicity of the deaf Matlin acting like he is too loud even for her. They’re an unexpectedly perfect double act.

Roaster: Amy Schumer
Roast: Charlie Sheen (2011)
Schumer also broke out thanks to the roasts. After a great set here, she got a Comedy Central hour special, then her own sketch show, and this week landed a deal to write and star in a movie produced by Judd Apatow. Schumer catches the audience off guard by seeming sweet and then saying the meanest of things.

Roaster: Patrice O’Neal
Roast: Charlie Sheen (2011)
It appeared the late O’Neal wrote jokes ahead of time, but after sitting through the roast, he instead decided to do what he does best: conversational riffing and being honest in the moment. The result is hilarious and such a contrast to the very set-up-punch-line rhythm of roast jokes. Sometimes nothing’s funnier than calling someone an asshole and meaning it.

Roaster: Anthony Jeselnik
Roast: Roseanne Barr (2012)
Known for dark one-liners, Jeselnik is a natural for these roasts. His Barr set was his best, because, more so than his other two, his dark flourishes were in service of the insult and not the other way around. It was a night of fat jokes, and Jeselnik’s were transcendent.

Roaster: Andy Samberg
Roast: James Franco (2013)

In a way, Samberg’s roast set is the spiritual descendent of MacDonald’s. Just like MacDonald’s set, the crowd takes a second to figure out what the hell is going on. The difference is, Samberg’s set is a bit more satisfying because he roots his bad jokes inside a character: an idiot who doesn’t totally understand how roasting works. Also, the incredibly well-written set actually builds, getting sillier and sillier, and culminating with him finally doing one actual roast joke, perfectly describing Jeff Ross as a “melting hippo.”

Roaster: Natasha Leggero
Roast: Justin Bieber (2015)
Back for a second roast, Leggero was in the future Comedy Central development deal slot. And, boy, did she earn it. She hit harder than anyone else that night, with jokes both clever and mean. I was at the taping of this one, and I can tell the crowd exploded after this one: “Justin, Selena Gomez had to fuck you. She is literally the least lucky Selena in all of entertainment history.”

Roaster: Hannibal Buress
Roast: Justin Bieber (2015)
Few comedians are able to transfer their stand-up voice to roasts as well as Buress did. Buress used his version of deadpan directness to hit Bieber harder than people with more exaggerated jokes. This one moment should go down as one of the funniest, most unique in roast history:

Roaster: Jimmy Carr
Roast: Rob Lowe (2016)
Carr is known for his insults and edginess across the pond, so it was exciting to see him unleash on an unsuspecting audience. Carr is equal parts vicious and writerly, so his punch lines would be both harsh and trenchantly scripted. “Jewel has an incredible voice, an incredible body, and a face” is poetry. 

Roaster: Nikki Glaser
Roast: Rob Lowe (2016)
No reason to mess with a winning formula. For the Lowe roast, Glaser stepped into the Leggero-Schumer-Jeselnik slot, and like those before her, she destroyed. In a night full of setup–punch-line jokes, Glaser separated herself by using more misdirection and sneaking setups into transition. Ultimately, for almost everyone there, she had the best joke about them.

The 20 Best Comedy Central Roast Sets Ever