Top 20 Funniest Celebrity Roasts Ever

“The N.Y. Friars Club Roast of Drew Carey” (1998)
The 1998 roast of comedian Drew Carey was the first of the longstanding Friars Club Roasts to be publicly televised on Comedy Central. These events were notorious for their blue humor and bawdy content. Carey’s roast is substantially lighter in tone, although the old school feel of The Friars Club is still very much intact. Jeff Ross, predictably, kills it, setting the tone for the many times the comic would steal the spotlight in the years to come. Ross’ commentary about the average age of the guests in attendance speaks to the event’s classic vibe. Meanwhile, roastmaster Ryan Stiles keeps the whole thing together with class and a bright wit.

“The Dean Martin Celebrity Roast” (1974-84)
That “old school” feeling of the Friars Club Roasts got a chance to shine when Dean Martin hosted his own series of roasts back in the 1970s and ‘80s. These specials will likely ring more nostalgic for viewers of a certain age, particularly those who remember when Dino himself was the victim. The many roasters who poke fun at the Hollywood icon largely take the easy road with numerous quips about Martin’s famously inebriated public persona. Jokes about the Rat Pack are also obviously featured, and it’s a good time all around. Just look at how enthusiastically everyone reacts! It's classic stuff.

“Comedy Central Roast” (2003-)
Half the fun of watching a celebrity roast can be the roaster’s skewing of other guests. No one is safe from Amy Schumer when she comes on stage for Roseanne Barr’s roast. She takes fiery pot shots aimed squarely at everyone in attendance. Then, she sets her sights on the guest of honor. Of course, Shumer isn’t the only highlight here. “Married... with Children” actress Katey Sagal also delivers a memorable set, while Barr herself is even good-natured about the appearance of her ex Tom Arnold. She can’t resist slipping in a few digs at him, but it is a roast, after all!

“The N.Y. Friars Club Roast of Rob Reiner” (2000)
The New York Friars Club Roast of Rob Reiner was another early televised roast on Comedy Central. It also speaks largely to the controversial nature of the medium’s vintage style of comedy. Here, however, it sort of makes sense, as Reiner had been among the cast of one of television’s most groundbreaking sitcoms, “All in the Family.” Reiner takes all of the jokes in stride, including a set from Triumph the Insult Comic Dog. The latter pokes fun at Reiner’s resume and appearance, while other subjects include his marriage to “Laverne & Shirley” star Penny Marshall. Some of the gags are dated, but the event can still serve as a fun link between comedy roasts of the past and present.

“Comedy Central Roast” (2003-)
It’s an understatement to say that the late Greg Giraldo is missed by fans of truly ruthless comedy. The man had so many iconic roast moments that it's truly difficult to pick a favorite. Giraldo’s set from the Comedy Central roast of Flavor Flav might just be the man’s shining hour, however. It’s that good. Every barb and insult almost sounds poetic erupting from his mouth. They cut to the heart of each target with some fairly transgressive results, yet Giraldo’s delivery is so likable, that he gets away with it! Seriously, if you haven’t seen this segment, watch it NOW.

“Comedy Central Roast” (2003-)
Fans aren’t always made privy to what goes on behind the scenes of a celebrity roast. Jokes are sometimes edited out of the taped broadcast. Other times, the subject in question has specific requests as to what’s fair game and what’s off the table. But David Hasselhoff reportedly laid it all out on the table for his roast, allowing the group of roasters to let loose with their best shots. And, his method pays off! The roast strikes the best kind of balance, as the truthful barbs fly while maintaining an aura of mutual admiration and respect. This one’s funny, mean, and everything in between.

“Comedy Central Roast” (2003-)
First off, it’s important to address the elephant in the room. We’ll admit, the news of James Franco’s alleged sexual misconduct may shine a different light onto this Comedy Central roast of his career. But it doesn’t make the actual special any less funny or entertaining. This is thanks largely to the level of talent on display with members including Nick Kroll, Andy Samberg and Bill Hader. Seth Rogen also does a great job as roastmaster. There’s no denying the fact that this is a great line-up filled with roasters who know how to tell a joke.

“Comedy Central Roast” (2003-)
Hey, remember when Donald Trump was just known as the real estate and television guy, as opposed to the 45th President of the United States? This Comedy Central roast was also notable for the backstage request by Trump concerning jokes about his finances. Gags commenting on discrepancies between his perceived value and real life worth were apparently a no-go, although we still think the roast is pretty damn funny. He goes along with the jokes for the most part, although his reactions do feel a bit stiff and forced. Still, the dais of roasters, which includes Marlee Matlin (with an assist by Gilbert Gottfried) put in admirable performances.

“The N.Y. Friars Club Roast of Chevy Chase” (2002)
It’s no secret that many of Chevy Chase’s collaborators have found him to be a difficult presence on set. Still, he’s arguably one of the best to ever do it. But we admit it is definitely fun to see him in the hot seat here. Stephen Colbert lays into him with an intelligent ruthlessness. Chase’s “National Lampoon’s” co-star Beverly D’Angelo also injects her segment with humor, warmth, and… musical accompaniment? Indeed, she performs a fun and frisky routine about life, love, and intimacy, making the most of her singing ability while making us laugh. It’s pretty wonderful.

“Comedy Central Roast” (2003-)
The late great Joan Rivers was another celebrity roast victim who actually had some requests prior to being skewered by Hollywood’s best and brightest. However, she simply wanted to nix comments about her daughter, Melissa. This request is honored easily enough, and the roast isn’t any less hilarious as a result. If anything, Rivers herself steals the show when she finally ascends the dais to exact some revenge. Her moment at the podium reminds us exactly how sharp, witty and intelligent she was as a writer, comedian and performer. Needless to say, it makes us miss the legend even more than we thought possible.

“The Dean Martin Celebrity Roast” (1974-84)
Members of The Rat Pack were always prime targets when it came to a Dean Martin celebrity roast, and the legendary Sammy Davis Jr. was no exception. The man’s song and dance pedigree is unquestionable, but that doesn’t stop many of his famous friends from stopping by to give him a hard time. It should be said that the often racially-motivated slant to some of the humor wouldn’t – and shouldn’t – necessarily fly today. But it doesn’t feel mean-spirited, and Davis Jr. takes it all in stride. After all, the saying goes, “we only roast the ones we love,” and Sammy Davis Jr. was loved by a lot of people.

“The Dean Martin Celebrity Roast” (1974-84)
“The Dean Martin Celebrity Roast” of Bob Hope is one of the best-remembered and most enduring of its day. It also served as a cool connection between the Friars Club roasts of old, and the new, edgier humor of the 1970s. Hope’s famous friends make a lot of great jokes at the entertainer’s expense. A lot of them went on to make appearances at other Dean Martin roasts, which is a testament to them. Don Rickles, John Wayne, and even a pre-Presidential Ronald Reagan get it on the act in this one. Naturally, Hope’s side-eye and facial expressions lean into every loaded gag and pun.

“The Dean Martin Show” (1965-74)
Speaking of President Reagan, he was still the Governor of California when he was “Man of the Hour'' for a Dean Martin celebrity roast, all the way back in 1973. It’s sort of surreal to see the future leader of the United States chumming it up with his Hollywood pals. Reagan’s path to the presidency is still a ways away during the event, but the dais spares no expense when it comes to tackling his political career. Don Rickles in particular gives him the business about being a celebrity attempting to govern, while the guest, to his credit, yuks it up the whole time. Who knew Ronald Reagan had such a great sense of humor?

“The Richard Pryor Show” (1977)
In the world of celebrity roasts, there are comebacks, and then there are Richard Pryor comebacks. Pryor’s roast actually took place on his own sketch comedy show in 1977. Although the series only lasted one season – with a mere four episodes – this moment when the cast roasts the star is insanely memorable. Specifically, it’s when the comedian takes over and gives it back that things truly kick into high gear. A young Robin Williams notably fends off a particularly strong blast of Pryor’s fiery humor. It’s truly a shame that we only got one such roast on the short-lived show, because it’s top-notch stuff.

“The N.Y. Friars Club Roast of Hugh Hefner” (2001)
Celebrity roasts have always been a treasure trove of memorable moments, but this next one featured one truly infamous joke. The Friars Club roast of Hugh Hefner was taped only weeks after the tragic events of September 11 2001, with many still wondering when it would be appropriate to make people laugh. Gilbert Gottfried tried to make a joke about the event, and the reaction was, well, negative. However, Gottfried then launched into what was perhaps the greatest telling of the crudest joke ever, “The Aristocrats,” and ended up getting the crowd on his side. The full footage never made it to air, but clips of the incident can be seen both in the 2005 “The Aristocats”, and 2017’s “Gilbert” documentaries.

“The Dean Martin Celebrity Roast” (1974-84)
Who has the guts to insult the Chairman of the Board? Well, a lot of people, actually, and the results speak for themselves. Not all of the Dean Martin celebrity roasts contain humor or references that are recognizable today.. Yet Sinatra’s enduring public persona is such that the jokes here still feel very funny and fresh. This is largely due to Ol' Blue Eyes’ reputation as a tough guy, and his reported mob connections. We’d also be remiss not to mention the stories of bad behavior that always followed him and The Rat Pack. As a result, segments from the likes of Ronald Reagan, Ruth Buzzi and, yes, Don Rickles again, make this celebrity roast one of the all-time greats.

“Comedy Central Roast” (2003-)
Few celebrity guests are perhaps as ripe for parody as the iconic William Shatner. Every comic worth their salt has some form of Shatner impression hidden somewhere in their back pocket, a Captain Kirk for all occasions, if you will. And yes, this does certainly come into play with some of the jokes here on this special, but roasters on the dais also spend time talking about things like Shatner’s personality, talent, and age. George Takei gets in on the act, while Leonard Nimoy turns up in a pre-taped segment. And did we mention the inimitable Betty White is there? What more could you ask for?

“Comedy Central Roast” (2003-)
Charlie Sheen is another celebrity whose personal behavior and run-ins with trouble made him a prime target to be roasted. And Comedy Central spares no expense, delivering the goods with what has to be one of the best of their modern celebrity roasts. They even manage to nab Guns N' Roses guitarist Slash to play Sheen into the show, making the affair truly feel like a rock ‘n roll party. The guest of honor’s peers do a great job at pointing out his shortcomings, while still recognizing his talent and influence as an actor. In other words, it’s roast gold.

“Comedy Central Roast” (2003-)
It would’ve been easy for the Comedy Central roast of Pamela Anderson to have flopped, were it not for the grand sense of humor of its honoree. The former “Baywatch” star has always been able to laugh at herself, and it’s this graciousness that shines through as each roaster takes turns focusing on her appeal, and, well, “attributes.” Anderson isn’t the only target, however, as Courtney Love gets hers from the dais, as does fellow roaster Bea Arthur. The whole thing is raw, slightly sleazy, and feels like it’s gonna fly off the rails at any time. We love it.

“Comedy Central Roast” (2003-)
It feels fitting that we honor two comedians who left us far too soon: the aforementioned Greg Giraldo, and roast subject, Bob Saget. Giraldo offers up a blast of hot fire when he lays into Saget, targeting the “Full House” man’s sense of artistry. Meanwhile, Norm MacDonald does the unthinkable, bombing on purpose! His set is probably the best gift he could’ve given Saget – and us as viewers. It’s truly a “comedian’s comedian” move of meta-brilliance. Beyond this, however, the Comedy Central special does what every good roast should: it pushes boundaries, celebrates an icon’s career, and, most importantly, makes us laugh.