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.