A different version of this post ran on August 28, 2013, before the James Franco Roast. We have updated it following the Rob Lowe Roast.
A good roast joke is undeniable; it’s comedy at its most immediate and visceral. Cruel, harsh, and tasteless, sure, but also very, very funny. So with Rob Lowe getting roasted last night on Comedy Central (here are the best 18 jokes from it), we wanted to look back at the sets that set the roast bar at its highest. We went back through all the previous Comedy Central roasts (which were televised Friars’ Club Roasts through 2002) and picked the 16 absolutely funniest single sets. (We limited it to one per comedian, so the list didn’t end up being half Greg Giraldo.) Be warned, the language is super NSFW, unless you’re a sailor, truck driver, or Jeff Ross. 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.
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.
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.
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.