There is perhaps no task more difficult for an entertainer than serving on the dais of some poor-but-lovable celebrity’s roast. Sure, it already takes serious guts for a comic to stand in front of a packed house and make everyone laugh a la truTV’s new Comedy Knockout, but when your job is to insult everything about a person, from their looks to their résumé, and make them and an even bigger audience laugh in the process, well, you better damn well bring your best game. There’s a fine line between being hilariously mean and bombing to the collective gasp of a crowd, and only a handful of comics have ever been able to truly dominate the art of the roast.
What’s unfortunate for roast aficionados, though, is that we don’t even get to see some of the best insults, jokes, and routines each year, because the biggest events are often private. And while we most often associate the art of the roast with the events that are televised, the best and often most brutal jabs come from behind closed doors, or even at the events that happened decades before we were born. That said, let’s take some time to acknowledge, honor, and rank some of the most hilarious roast takedowns we’ve ever heard.
8) Jeff Ross redefines ‘too soon’ with his Jerry Sandusky jokes
When it comes to the modern roast, Jeff Ross is the first name on everyone’s list. He’s a master of one-liners that range from dumber than dumb to insanely clever, and he’s so good that even his very first roast joke managed to make Steven Seagal hate him. In recent years, he’s added ridiculous costumes to his repertoire, including a Joe Paterno outfit for the 2012 roast of Roseanne. His most brutal moment, which is hard to find and not included above, came when he responded to the audience’s collective gasp over a Jerry Sandusky joke that came at Jane Lynch’s expense: “Folks, if you’re offended by what you see tonight, just do what Joe Paterno did – look the other way.”
7) Greg Giraldo sets the Blue Collar trailer park on fire
If you want to highlight the best roast work of the late Greg Giraldo (still hurts to call him that), you could put every joke into a hat and just draw them at random. In the 66 years since the Friars Club first roasted Sam Levenson, many comics have offered up their best insults and Giraldo was undoubtedly one of the all-time greatest. Arguably his finest, meanest performance came at the 2005 roast of Jeff Foxworthy, at which the other Blue Collar Comedy stars — Bill Engvall, Ron White, and Larry the Cable Guy — served as roastmasters. Giraldo’s opening takedown of the average Blue Collar fan had everyone, including the Redneck of the Hour and his cohorts, laughing their asses off to lines like: “This is money they could have spent on abortions or crystal meth.” There will never be another Greg Giraldo.
6) Anthony Jeselnik’s offensiveness flies right over your head
Kate Walsh, Steve-O, William Shatner, the late, great Patrice O’Neal – no one was safe from Anthony Jeselnik at Charlie Sheen’s roast in 2011. But the dry comic’s best joke was probably perceived as a bomb by most people in the audience, as he pondered, “What can you say about Mike Tyson that hasn’t already been the title of a Richard Pryor album?” It was a thinker, though, and O’Neal definitely got it, offering Jeselnik a round of applause for one hell of a subtle way of saying a very bad word. The only drawback of Jeselnik’s roasting power is that sometimes his jokes just go too far, and even the tiger-blooded Sheen can’t take the heat.
5) Howard Stern gives Joan Rivers a standing ovation
For his 2014 birthday bash, the King of All Media, Howard Stern invited Jeff Ross and Joan Rivers out to perform their own roast, and it took Rivers one line to lower the bar straight to hell. Sure, the offensive duo had plenty of cringeworthy-yet-hilarious material to unleash on Stern and the audience, but Rivers saw low-hanging fruit in Tan Mom’s presence at the event, and holy moly did she ever detonate a nuke: “Her kid is the only kid who wishes her mother was Casey Anthony.” Judging by Stern’s reaction, that was certainly one of the best birthday gifts he received that year.
4) Paul Mooney has a fatherly appreciation of Richard Pryor
The 1977 roast of Richard Pryor is a must-watch in its entirety, featuring hilarious performances by John Witherspoon and Robin Williams, who would later serve as roastmaster at Pryor’s Friars Club Roast in 1991. But it’s Paul Mooney who sets the standard early on, saying of the iconic Pryor: “He’s always been very funny. He was born in Peoria, where half the kids in the town call him a superstar these days, and the other half call him daddy.” Did Mooney have more jokes after that? It’s hard to tell because that one line simply couldn’t be topped.
3) Jennifer Love Hewitt never saw Sarah Silverman coming
Carson Daly was such an important part of MTV in the late ‘90s and early ‘00s that when he left for a gig as the late, late, late, latest night talk show host on NBC, the music video channel honored him with a roast. Nelly sat next to him and popular comics and C-listers gave him hell. It was a fun time had by all. Except for maybe Daly’s ex, Jennifer Love Hewitt, who caught some volcanic heat from Sarah Silverman with her unique delivery. “People say you’re the next Audrey Hepburn,” Silverman deadpans. “Does that scare you, knowing you’re going to die of colon cancer?” And that’s before she even mentioned Love’s singing career.
2) Dean Martin wasn’t only a host, he also brought the fire
If there’s one thing that can be said about Dean Martin’s performances at all of the many roasts that he hosted over the years, it’s that he was totally sauced. But just because he became increasingly inebriated as an event unfolded didn’t mean that he couldn’t dish out the same outrageousness that his friends and peers were lobbing his way. Just ask the legendary Don Rickles, who was always compared to some of the worst people in history by those who loved him. At the roast of Ronald Reagan, Martin put Rickles in the worst company imaginable while trying to solve his anger issues: “Everybody wants to know why Don is so mean. He’s been that way ever since he found out Eva Braun was two-timing him.”
1) Nobody could ever outdo the “Master of Malice” Don Rickles
So, how mean is Rickles? He roasted Milton Berle and their mutual friends at Berle’s funeral. At Ronald Reagan’s second inauguration in 1985, Rickles went after Webster star Emmanuel Lewis, who was 14, but looked five, with an insult so biting and edgy that it would inspire a million think pieces today. And so it goes without saying that Rickles’ greatest takedowns came at his own roast, as he paid everyone back for the things they said about him. There’s too much to quote, so just watch him annihilate George C. Scott until the man who played General Patton waves a flag in surrender. All these years later and Rickles remains so good that he can roast a celebrity like Justin Bieber without even saying a word.
See more epic comedy takedowns when truTV’s ‘Comedy Knockout‘ premieres tomorrow at 10:30/9:30c.