Top 10 Savage Celebrity Roasters

#10: Anthony Jeselnik

Also in:

Comedian Anthony Jeselnik: What You Can't Say at Roasts

Jeselnik is the head of a new generation of roasters. The stand-up comic started as a behind-the-scenes writer for the David Hasselhoff roast, but producers liked his style and he was offered a performing role at the following event. The 2011 roast of Donald Trump spring boarded his comedy career, as his dark, faux-psychopath Patrick Bateman style mixed with masterful joke-writing made Jeselnik an instant comedy celebrity. He made mincemeat of his fellow roasters and of course the Donald himself, and would apply the same technique to later roasts of Charlie Sheen and Roseanne Barr before moving into different comedic ventures.

Meanness personified is Nick DiPaolo; a no-holds barred, take no prisoners performer whose roast sets are leagues above the competition. The veteran comedian first gained national notice as a ball-butcher on the 2003 Roast of Denis Leary, where he eviscerated the stage and the grumpy Leary so well that he became a roast regular. DiPaolo made additional appearances at the Comedy Central roasts of Jeff Foxworthy, Pamela Anderson, and Larry the Cable Guy, and brought the house down every time. His lesser-known but perhaps most revered appearance was at the Howard Stern roast of Artie Lange, where he blurred the line between horrifying and horrifyingly hilarious.

#8: Amy Schumer

Also in:

Top 10 Celebrity Trump Haters

After appearing on NBC’s Last Comic Standing several years before, Amy Schumer got her big break with the 2011 roast of Charlie Sheen. Six million people tuned in to see the largely unknown comedian trounce the competition like few others could. Schumer was both hilarious and ruthless in her dissection of Sheen and company, but courted controversy with a joke aimed at Steve-O about his Jackass co-star Ryan Dunn’s then recent death. There’s no doubt that this was the set and that propelled her career, and earned her respect as a roaster. Schumer later appeared on the roast of Roseanne Barr the following year, serving another cocktail of razor-sharp quips before ascending to a higher level of show business.

Gilbert Gottfried is perhaps best known for his obnoxious voice, but comedy fans know him as a rare, fearless genius. Gottfried is also a legend in roasts, dating back to the 2001 Friars Club Roast of Hugh Hefner, where he made an infamous joke about the very recent 9/11 terror attacks. Winding a comedic yarn as no other performer could, Gilbert weaves outlandish stories into his act, along with sharp one-liners, to create a roast performance unlike most. Gottfried was embraced by Comedy Central for their modern roasts, and luckily, he’s never wavered from his offbeat and off-color style of humor. As of 2016, he has performed at seven of their roasts, allowing comedy fans to bask in his offensive glow... whether they want to or not.

Norm Macdonald made just one roast appearance, but it’s the most conceptually hilarious set we’ve ever seen. In direct response to a producer telling him to be “shocking,” Norm decided to borrow material from a 1950s retirement party book; so that meant egregiously corny and outdated jokes that countered the brutal Comedy Central roast formula. What followed was a performance that confused, stunned, and shook the audience, as the comic delivered benign jokes with feigned sincerity - effectively roasting the concept of the roast. Sure, the audience was disoriented, but the rest of the panel was doubled over laughing, as were those viewers who were “in the know” about Norm’s abstract and provocative nature. Years later, no single roast set is more infamous or admired.

Try as they might, but no one can go shot for shot with Lisa Lampanelli. The “Queen of Mean” became famous solely from her roast performances, which started back in 2002 at the Friars Club Roast of Chevy Chase. Lampanelli’s no-boundaries sharp wit proved to be a perfect fit and she saddled up for 10 years of near-annual roast appearances. Her shocking material and bold delivery had a profound effect on her contemporaries, who had never seen a woman hold her own so well in a male-dominated game. Lampanelli would do more than hold her own, as she became the prized attraction at the Comedy Central roasts, and a fearless master of a brutal craft.

Richard Pryor is often considered the greatest stand-up comedian in history, and with his profane yet profound humor, it’s no surprise he’d be a perfect roaster. Pryor was a roast virgin when the short-lived Richard Pryor Show decided to hold a roast. He sat hunched and quiet, as many of showbiz’s top stars ridiculed and insulted him, including Paul Mooney and Robin Williams. But, when Pryor was given his chance to respond, he torched the room. The God of obscene comedy left the other roasters in ruins, and the audience in comedic heaven. We should’ve expected nothing less.

#3: Don Rickles

Also in:

Top 10 Cutest Celebrity Engagement Stories

Long before Comedy Central took over, the Dean Martin Celebrity roasts were the apex of the medium. Hosted by the famous crooner, the roasts were ratings blockbusters, and the king of these events was legendary ball-buster Don Rickles. It can be argued that Rickles is responsible for the mean nature of today’s roasts, as no one was more brutal in the comparatively wholesome 60s and 70s entertainment industry. No topic or person was off limits as Rickles made fun of every facet of show business, and people laughed harder than biologically possible. Based on the sheer audience of the Dean Martin roasts, it’s likely that Don will stand as the most popular roaster in history.

#2: Greg Giraldo

Also in:

Comedian Greg Behrendt: Why He's Just Not That Into You

Undeniably one of the most hilarious roasters of all time, Greg Giraldo is an icon of the medium. A Harvard law school graduate, Giraldo passed up a life of prestige for a life of chicken wings and drunks on the comedy club circuit. Like Lampanelli, he began his televised roast career in 2002 at the Chevy Chase gala, impressing the crowd with his remarkable wit and killer lines, and was soon commissioned for other roasts. From 2005 until his death in 2010, Giraldo performed at every Comedy Central roast; a total of eight appearances, the sum of which accounts for what we can only assume is the highest volume of roast laughs. Need proof? Just check out the Larry the Cable Guy, Flavor Flav, or Hasselhoff roasts and doubt no more. Before we unveil our top pick, here are a few honorable mentions: - Natasha Leggero - Drew Carey - Sarah Silverman - Todd Barry - Whitney Cummings

With roasting as his specialty, it’s fitting that he’s been called the meanest man in comedy. Starting as a fresh-faced 33-year-old at the Friars Club roast of Drew Carey, Ross’s style was tailor-made for the medium, as he stunned everyone with a perfect inaugural set. This would launch a career that’s spanned dozens of roasts from the Friars Club to Comedy Central, to Ross’s own TV specials. If there’s a roast, Ross will be there. He even inspired a club-hosted Roast Battle circuit that is making waves in the industry and launching the careers of young comedians. Now, Comedy Central has taken that concept to the small-screen, and Ross is the obvious architect. Well, he’s called the Roastmaster General for a reason! Do you agree with our list? Who’s your favorite celebrity roaster? For more hysterical Top 10s published daily, be sure to subscribe to WatchMojo.com.