The Most Controversial Comedians of All Time

Image via Getty/Michael Schwartz

If the past, we've looked at Chelsea Handler's most controversial comments—if that wasn't enough to sway you, we'll spell it out for you: Handler says whatever is on her mind, and apparently her mind can be a vulgar, mean, and occasionally pretty racist place.

Remember that in 2011, she pissed off the entire country of Serbia by coming to the defense of Amy Winehouse, who the Serbian Defense Minister had called a “shame and disappointment.” In response, Handler read the statement aloud during an episode of her E! show, Chelsea Lately, and followed it up with, “Well, so is your country.”

Handler has tamped it down a bit since moving to Netflix and focusing on less frivolous matters, but once a loose cannon, always a loose cannon.

Another influential comedian before his time, Dick Gregory was one of the first African-American funnymen to change the way that the public viewed black people in comedy back in the 1960s. Comedy at the time had only ever been influenced by minstrel shows that promoted offensive stereotypes. His act was absolutely controversial at the time because of the subject matter, but one of the best things about him is that he managed to keep it all respectful. Through his jokes, he was trying to convey how ridiculous racism and segregation was.

One such quote: “I am really enjoying the new Martin Luther King Jr, stamp. Just think about all those white bigots, licking the backside of a black man.” True BAMF.

Louis C.K., the man with the best comedy on TV right now, has, duh, experienced backlash. His outspoken but sobering views on race—one of his most well-known bits is called “It’s Great Being a While Male”—and politics have fixed him in the limelight. He reportedly had some problems after posting a series of “drunken” tweets about Sarah Palin that were rather explicit. And then in 2017, he stepped into controversy again by making some off-color comments about child molestation during his opening monologue as host on Saturday Night Live.

Lewis Black’s shtick is to take on gigantic, complicated political matters and whittle them down into a hilarious, exasperated one-liner. Like Jon Stewart, Black does this in large part to shame the news.

His stand-up is explicitly political, but rather than lean too far in one direction, he spews hate at both Democrats and Republicans equally. In the past, for example, he’s joked: “What's the difference between a Democrat and a Republican? A Democrat blows, a Republican sucks.”

Andrew Dice Clay has such a history of explicit and profane material that he was banned from MTV in 1989 for reciting what he called “adult nursery rhymes” during the VMAs. Considering that the routine involved a poem that began, “Little Bo Peep fucked her sheep,” this isn't surprising.

The ban was lifted in 2011, but Clay hasn’t stopped being any less crude—apart from an appearance on The Arsenio Hall Show in 1990 when he broke down in tears in response to accusations of misogyny.

In 1990, Clay had hosted an episode of Saturday Night Live, famously prompting cast member Nora Dunn and the scheduled musical guest, Sinead O’Connor, to boycott the episode because of his participation.

The original troll, Andy Kaufman's brand of comedy was something close to performance art, with the comic staying in character and pulling stunts to the dismay (and sometimes delight) of everyone around him. He was such a prankster that, when he died from cancer in 1984, many believed that he'd faked his death. But even Kaufman had limits.

One memorable prank went down in 1981, during film of the sketch comedy series Fridays. Kaufman, performing with cast members including Seinfeld star Michael Richards, refused to say his lines on camera, prompting a brawl between Kaufman, Richards, and series producer Jack Burns. This was later revealed to be a practical joke that all three were in on.

Kaufman was also widely known for his work on ABC's Taxi, in which he portrayed Latka Gravas. Audiences loved Gravas so much, they wanted him to do the bit during his stand-up routines. Knowing this was expected from him, Kaufman would sometimes “punish” his audience by reading F. Scott Fitzgerald’s The Great Gatsby until the entire audience had left.

Lisa Lampanelli's shtick is so notorious, she's known as “The Queen of Mean.” Her stand-up routines are fixed around insulting as many people as possible, with Lampanelli making un-PC remarks about race and homosexuality. For instance, here's Her Highness riffing on Rihanna and Chris Brown during Comedy Central's roast of Larry the Cable Guy: “You've beaten that concept so hard it's now dating Chris Brown.” 

Lampanelli’s appearance on Celebrity Apprentice years ago wasn't without controversy, either. Though apologies were demanded of her, she refused to offer a mea culpa for using racial slurs during her stint on the series.

If you've seen one of Ari Shaffir’s "Amazing Racist" bits, you already know—Shaffir will be an utter jackass for attention. His skits in this character were filmed for the DVD release of National Lampoon’s Lost Reality, but they produced more drama than laughter. One skit involved Shaffir picking up some Mexican men at a Home Depot by telling them that he had construction work. But he didn't, and, well, just listen.

David Cross received significant positive attention for his hilarious portrayal of Tobias Fünke on the beloved Arrested Development. It was a big change from the criticism he’s received for his stand-up. The comic has no problem with working rough chuckles out of subjects like misogyny and religion—specifically the Catholic church. He also made headlines after claiming to have done coke at the White House during the Correspondents' Dinner in 2009.

During an appearance on Conan, Cross bashed the film he was there to promote, Alvin and the Chipmunks: Chipwrecked, calling it one of the worst experiences of his life before telling everyone that they shouldn’t see it. Preach?

Chris Morris loves pissing off the British media, if his 2001 satirical special, Brass Eye, is any indication. In the piece, he examined the way that the media handles the reporting of pedophilia by suggesting that they get hysterical and sensational, which angered journalists, politicians, and the general public. After airing the special, Channel 4 reportedly received over 3,000 complaints, and overnight Morris became one of the most hated men in the UK.

Channel 4 defended the show, however, saying that Morris was mocking the media, not the victims.

Tracy Morgan won over many with his performance as Tracy Jordan on the now dearly departed 30 Rock, but, as many comics have shown, it only takes one incident to tarnish your rep. In Morgan’s case, a bit during a stand-up performance in Nashville turned ugly when he launched into a homophobic rant, where he claimed that if he had a son who was gay, he’d stab him.

Though he apologized and poked fun at the incident in a subsequent episode of 30 Rock, it remains a massive blemish on his career. 

If this list is any indication, comedians need a certain amount of controversy surrounding their stand-up if they want to be at all famous. No one talks about the socially sensitive guys, and that’s not going to sell any tickets. Of course, there’s a very thin line between a controversial joke and a joke gone too far, but a good comedian knows how to straddle it accordingly; Daniel Tosh is not one of those comedians.

It seems there are no limits to what Tosh will poke fun at, whether on his Comedy Central series Tosh.0 or during stand-up routines. Rape? Fair game. People’s appearances? Of course. Dead babies? Sure. For instance, on one specific occasion, Tosh performed a stand-up routine that included a joke about rape, and when a female audience member yelled out that he wasn’t being funny, Tosh responded with, “Wouldn’t it be funny if that girl got raped by like, five guys right now? Like right now? What if a bunch of guys just raped her…” Defenders of his comedy claim that people are just being too sensitive, and critics of his comedy claim that he doesn't know how to take criticism.

Whatever the case, though, his controversial jokes have definitely gotten the spotlight to shine on him. Whether or not it’s a good light is open to interpretation.

Tommy Gavin from Rescue Me isn't one of the funniest guys, but the dude who played him certainly is. A long-time stand-up comic, Denis Leary has always wanted to make the audience squirm. But it's not just his jokes that have earned Leary negative attention. See, Leary was good friends with another comedian on this list, Bill Hicks, until Leary's comedy album, No Cure for Cancer, was released in 1993. The release destroyed their friendship, as it was widely believed that Leary had stolen his material and overall stage persona from Hicks.

In 2011, Leary released a parody video of “A Charlie Brown Christmas” that found the iconic character converting to Islam and constructing a faulty bomb. 

Michael Richards received many accolades and respect from the Hollywood community for his iconic role as Cosmo Kramer in Seinfeld between 1989 to 1998, but as many other comedians before him also found out, it only takes one incident to tarnish years of success. In Richards’s case, the career-killing event occurred during a 2006 stand-up performance at L.A.’s Laugh Factory comedy club, where he took to making racist remarks, including use of the n-word, to some African-American members of the audience who were being loud during his set.

He apologized for the incident soon after and even appeared on his former Seinfeld boss’ new series, Curb Your Enthusiasm, as himself to reference and make fun of the incident. But the damage was done. Over six years later, the scent of Richards' racially-charged meltdown still lingers around his three-time Emmy-winning performance as Kramer. Interestingly, Richards’ meltdown was one of the first of its kind to be caught on camera and go viral on the Internet (thanks to TMZ.

Sarah Silverman isn't scared. Her stand-up routines and her Comedy Central series, The Sarah Silverman Program, routinely confront racism, abortion, and religion without pause, she named her 2005 documentary Jesus is Magic, and has even done a bit about how 9/11 was the worst day of her life—because it was the day that she found out a soy chai latte had 900 calories. 

Silverman has cleverly embraced stereotypes about the cuteness and meekness of women to deliver the most caustic jokes, and it's brilliant, although not without controversy: See the fake photos of her before and after an abortion, which she put up on Twitter in response to Mitt Romney’s intentions to overturn Roe v. Wade.

Thanks to his run as host of The Daily Show, Jon Stewart will be remembered as one of the best comedians on television. Of course, his liberal views have gotten him into hot water, especially with folks in media. He was so hated by former CNN anchor Rick Sanchez that during an interview that aired on Sirius XM, Sanchez called Stewart a “bigot,” in addition to accusing him of being “uninformed” and “prejudicial.” Sanchez was fired from CNN a day later, presumably for his remarks.

Despite the verbal darts aimed at him, Stewart enjoys a spot as one of the most influential members of the media, even after his hosting stint ended. He’s publicly stated that he never wanted to be the sole source of news for people, because at the end of the day, he’s still a comedian; his point has always been that the media's version of political discourse in this country is broken. When there are only clowns to get your news from, something is wrong.

And so, yeah, Fox News really hated him for that.

For the sake of comedy, Roseanne Barr will get dirty. The former sitcom star has invited controversy her entire career, most memorably in 1990 when she performed a rendition of “The Star-Spangled Banner” before a Padres game in San Diego. During the performance, she deliberately sang in a loud, grating tone, and afterwards, she made a point to mimic baseball players by spitting on the ground and grabbing at her crotch.

Off the diamond, she’s called Israel a “Nazi state,” and—though she does support same-sex marriage—has used a variety homophobic words, mostly in the early '90s, as insults. Makes the fact that she ran for president under the Peace and Freedom Party more than a little ironic, doesn’t it?

Many Americans aren't familiar with Boyle, but across the Atlantic, the comic is notorious for his disregard for boundaries. His repertoire reads like a laundry list of dumb shit, or the lunch-room banter of middle school boys: He’s poked fun at disabled athletes participating in the Paralympics; he’s said made offensive remarks about the Queen; and he’s performed routines about those suffering from Down syndrome. It goes without saying that his sets frequently involve potentially racist and sexist material.

Because of these things, he's faced the BBC numerous times over allegations that his jokes are too offensive to be broadcast. Naturally, it doesn't appear to have hurt his career much (a 2011 libel lawsuit against The Mirror, accusations of tax evasion, and a 2013 set that was entirely cut from the BBC broadcast of a charity event, notwithstanding).

The answer to the headline of a 2006 feature on this guy in British GQ, “Is This America’s Most Depraved Man?” depends on who you ask. When it comes to boundaries, it doesn’t seem like Doug Stanhope has many. Jokes about subjects like terrorism, misogyny, and suicide are completely fair game, and much of his stand-up tends to be about politically charged subjects in a fashion so offensive that, in 2004, a total of 600 people walked out of one of his gigs.

The thing about his stand-up, though, is that it’s also completely self-aware. It’s clear that he just wants to mess with people, and he plays upon their sensitivities well. Depraved or not, by doing so, he’s become one of the most notoriously controversial guys out there. And, of course, we all know the saying in Hollywood: Any press is good press.

A circus man who landed his first professional writing gig working on material for Richard Pryor, Paul Mooney is a comic without a filter. On race and politics, he will speak whatever is on his mind, and because he's often telling the truth, lots of folks catch feelings.

During the days of Bush II, an act of Mooney's was cut short during taping for Showtime at the Apollo because of comments from the comedian about the President. The offending line? "Fuck the Bushes. I hate the whole family. Like that mother of his, she looks like the guy on the Quaker Oats box." As a result, Mooney vowed to never again work at the historic Harlem theater. This is just one moment in a long body of work meant to expose American inequality.

Bill Maher built a career around controversial statements about those two subjects polite Americans aren't supposed to talk about: politics and religion.

Have a taste: Back in 2001, shortly after the September 11 attacks, Maher stated that he disagreed with President George W. Bush after the President called terrorists “cowards.” Maher responded by saying that, “[the US military] have been the cowards, lobbing cruise missiles from 2,000 miles away. Staying in the airplane when it hits the building, say what you want about it, it’s not cowardly.”

This remark got his Comedy Central show Politically Incorrect with Bill Maher cancelled. Lucky for him, HBO gave him a platform in 2003, with Real Time with Bill Maher. And unluckily for HBO, Maher used the platform to continue to draw ire from all sides, as in 2017, when he dropped the N-word without a moment's hesitation.

Years removed from his passing, Richard Pryor remains one of the most influential comedians in history. Drawing from his own life experiences, he brought light to issues like poverty, racism, and drug abuse, all the while paving the way for African American comedians. Without Pryor, the landscape of modern comedy would look very different.

As for controversy, his many specials and shows were often deemed too risqué for their time, especially during the late '60s and throughout the '70s. His four-episode 1977 sketch comedy series on NBC, The Richard Pryor Show, included skits where he portrayed a rock musician who kills every white member of his audience with a machine gun, and a bit where a woman describes her first lesbian experience. Pryor went there with aplomb.

Bill Hicks was described as “the most dangerous comedian in the world,” and it’s not without good reason. During a performance in Scotland, Hicks forced an audience of 300 to tears with a stand-up routine that criticized everything from politics to abortion, and told members of the media that they should “kill themselves” because they’re “Satan’s spawn.”

This is all the kind of stuff that Hicks’ career was based off of. He defined his dark stand-up as “cynical humanism,” and there was rarely a bit that didn't focus on religion, sex, drugs, politics, or the media in a manner that some people today would still find extremely offensive.

One of his most controversial quotes: “You ever notice that everyone who believes in creationism looks really unevolved? Eyes real close together, big furry hands and feet. 'I believe God created me in one day.' Yeah, looks like he rushed it.” Can you imagine how many heads would explode at Fox News?

There aren’t many comedians whose stand-up specials prompt a whole U.S. Supreme Court case, so George Carlin was special in that regard. Known for his dark sense of humor, Carlin was a controversial funnyman throughout his whole career, but it wasn’t until the 1970s and his “Seven Dirty Words” comedy routine—which lists off “the seven words you can never say on television”—that he really became historic and, more or less, changed the entire landscape of broadcast radio and television.

If you’re not privy to how Carlin did this, here’s a mini-history lesson: In 1973, a father filed a complaint with the FCC stating that he’d turned on the radio with his young son present in the afternoon, and they’d been subject to Carlin’s “Seven Dirty Words” routine, which included such curse words as “shit,” “piss,” “fuck,” “cunt,” “cocksucker,” “motherfucker,” and “tits.”  The FCC sent a letter of censure to the company that owned the radio station, Pacifica Foundation, and the case—known as FCC v. Pacifica Foundation—went to court. In 1978, the Supreme Court ruled that the routine was “indecent, but not obscene,” and gave the FCC the power to prohibit any broadcasts they deemed indecent during hours when children could possibly be watching or listening—specifically, between the hours of 6 AM and 10 PM local time. The rest of the time is known as the “safe harbor” hours, and the FCC won’t take action against any indecent material aired then. Generally speaking, though, networks don't like to air anything too risky anyway, regardless of this rule.

In short, the fact that there’s no curse words or nudity on network television is all because of Carlin. 

In the 1960s, American comedy experienced a change, and that change was called Lenny Bruce. During a time when mainstream comedy was squeaky clean, Bruce got nasty. His language was so controversial that in 1961, he was arrested under charges of obscenity for using the word “cocksucker” during a stand-up performance in San Francisco. He was acquitted, but his case became a lesson about what one could say in public. It would not be his first arrest.

In 1964, he was publicly arrested under charges of obscenities used during a performance—this time in New York City—and convicted, despite testimony from most of the well-known names in Greenwich Village at the time, including Woody Allen, Bob Dylan, and Allen Ginsberg. He was bailed out of his sentence of four months in a workhouse, and eventually his case received a full pardon after his death in 1966.