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10 Most Controversial Comedians of All Time

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Controversial comedy; where would we be without it? For almost a century it has been the task of new generations of comics to help us deal with social and political pains in the ass by getting up on stage and making us laugh at all that is sacred. After all, what could be more enjoyable than that moment when a genuinely funny comedian makes the kind of crack that compels a whole nation to hold their collective breath and think to themselves in unison, “Oh no you didn’t!”? Here we raise a glass to the top ten most controversial comedians of all time.

10. Andy Kaufman

Kaufman was the king of self-deprecating, ambiguous performances and stunts on live television. The showman and star of Taxi was infamously difficult to work with, frequently ruining takes and exploiting the cameras for his own subversive skits. Indeed, he was so consistently obsessed with seemingly ruining his own reputation that he became blacklisted by countless television studios. Amongst his many stunts, Kaufman infamously decided to punish a live audience at one of his own shows by painstakingly reading aloud a novel from cover to cover until the stalls had emptied in frustration. He also faked a celebrity feud with Jerry Lawler, culminating in an on-screen fight on The David Letterman Show which led to him injuring his neck. Ten years later the whole skit was revealed as a prank. Many even claim that Kaufman faked his own tragic death from cancer in 1984 and is still alive.

9. Lenny Bruce

Lenny Bruce was the father of all comedic controversy. The rising star of the comedy circuit in the 1960s was arrested on obscenity charges countless times following a show in 1964 in which he simply uttered the word ‘cocksucker.’ He was reputedly blacklisted from almost every major comedy venue in the United States and was eventually convicted and ordered to serve four months in a workhouse. His hounding by the feds led to a massive reevaluation of the obscenity laws in the U.S, with Bruce receiving support from such fellow artists as Woody Allen and Bob Dylan. He died of an overdose, aged just 40, and was the first person ever to be granted a posthumous pardon by the State of New York.

8. Richard Pryor


In 1967, Richard Pryor walked onto the stage at a packed out Aladdin Hotel in Las Vegas after having what he described as an instantaneous epiphany, looked into the microphone and asked the audience, “What the fuck am I doing here?” before walking straight off again. Thus began the true career of the first African American to truly take comedy to a new level. Pryor began life as a safe comic selling out shows in safe venues for safe crowds; then he had this ‘moment’ in Las Vegas. What followed were nearly three decades of him holding the torch for controversial and up-front comedy routines directly challenging racial stereotypes and laden with more profanities than a burns victim jumping into a pool of vinegar.

7. Dick Gregory

There are many younger fans of stand-up comedy who may never have heard of Dick Gregory, let alone know of his story, but back in the 1960s he was – quite literally – the first mainstream black comedian to make jokes about the racial issues gripping America at the time. Born in the South, Gregory was not only exceptionally funny but also deeply politically involved, taking an active part in the fledgling Civil Rights movements of the time. His skits, lampooning the Jim Crow laws and the arcane attitude of Southern whites, were not only popular with black audiences, but with white audiences as well.

6. Jon Stewart

‘Controversial’ not because of bad language or any other obvious staples of the average naughty comedian, Stewart has amassed an army of enemies – and an army of fans – through being one of the most intelligent and downright ball-bustin’ left wing political satirists of his generation. One of his more famous moments was his appearance on the political pantomime Crossfire in 2004, wherein – amongst other things – he pleaded with the hosts to cease with their “partisan hackery,” stealing the show and continually attacking its morals for the entirety of his interview. It led to a much publicized rivalry with Tucker Carlson and cemented his place in the annals of political lampooning.

5. Louis C.K.

A man who has a plethora of hilarious routines, and seems totally oblivious to the sensitivity of some of his potential audience, Louis C.K. has managed to rack up plenty of controversy points over the years. Approaching such subjects as killing his 4-year-old, and issuing a – reputedly – ‘drunken’ tweet explicitly attacking Sarah Palin, the comedian has unsurprisingly garnered much media attention. Through it all he’s maintained a large fan-base; google his frankly excellent line, “It’s great being a white male,” and see why.

4. Stephen Colbert

OK, so the left-of-center host of the eponymous Colbert Report may not be an obvious choice in a top ten list of controversial comedians, but we challenge you to watch his appearance at the 2006 White House Correspondents’ Association Dinner – in its entirety – and not come out at the end agreeing with our choice. In the face of almost total awkward silence, Stephen spent his quarter of an hour slot satirizing, undermining and ridiculing the entire Bush administration and half the country’s media, as they all sat there taking it. Although not initially widely picked up by the press, the video footage of the event became an internet phenomenon, leading to Colbert being awarded an award for ‘Ballsiest Comedian of 2006.’

3. Sarah Silverman

Magnificently walking the tightrope between Liberalism and political incorrectness, Silverman has enjoyed a decade of success telling jokes that satirize just about every aspect of American racism. After gaining her big break following a major controversy at the turn of the millennium – in which she extolled the benefits of using casual xenophobia in order to avoid jury duty – she’s managed to make cracks about every sore subject of the last 100 years. The Holocaust, AIDS, 9/11, nothing is too holy to avoid her scathing satire. She’s like a female, girl-next-door South Park, and through her subtle technique of playing devil’s advocate, she has benefited from controversy like no other.

2. George Carlin

Despite sadly no longer being with us, George Carlin’s routines are still some of the most watched clips on the internet, and he enjoys an almost unanimous public and celebrity fan-base. Controversial from the start, he spent his career undermining anyone or anything that dared try and impose a sense of power. His most controversial routine by far was his ‘Seven Words You Can Never Say On Television’ routine from 1972. The skit was a diatribe of profanities – including the deeply unpopular ‘C’ word – in an era when swearing in the media was not exactly looked upon lightly. Carlin was not only arrested for performing it live, it became such a hot topic that it went all the way to the Supreme Court. It was seen as a hallmark for regulations on control over speech within American broadcasting and even now probably isn’t safe for most TV stations.

1. Bill Hicks

One of the true gods of controversial, scathing comedy, Bill Hicks spent his entire short life performing, and pushing the boundaries of sensibility. He was one of the first and only comedians to publicly lampoon the Gulf War, and spent a decade of his career battling censorship issues over such subjects as the Resurrection and the handicapped. Described often as one of the darkest of comics, he even joked about his impending death while dying of cancer in the mid-nineties.



Written by Julian on February 9th, 2011 | Tagged as: Popular Culture


41 Responses to “10 Most Controversial Comedians of All Time”

  1. On February 10th 2011, Ben Sumner wrote:

    Sam Kinison! Eddie Murphy! (for the homophobic material alone)

  2. On February 10th 2011, jellen wrote:

    colbert, stewart and silverman combined are not as controversial as sam kinison was

  3. On February 10th 2011, James Thomas wrote:

    Jon Stewart and Stephen Colbert? Are you serious? These are two of the most mainstream, non controversial comedians out there. Sam Kinison should be on there definitely.

  4. On February 10th 2011, Ji wrote:

    How is Ricky Gervias NOT on this list?

  5. On February 10th 2011, Fluids wrote:

    Uhhh…no Kinison or Dice Clay yet there’s Sarah Silverman??? Are you kidding?? How about Howard Stern?? The writers youth and inexperience is really showing with some of these selections.

  6. On February 10th 2011, peabody wrote:

    Andrew Dice Clay is not on this list are you kidding me ? He was banned from everywhere

  7. On February 10th 2011, Toddbrew wrote:

    Sam Kinison?

    What the Fuck??

  8. On February 10th 2011, Tyler wrote:

    No Richard Pryor?… Really? John Stewart instead? Crap list without pryor.

  9. On February 10th 2011, Derrick E. wrote:

    The majority of you said everything I was thinking when I read this. Before I even started down the page, I just KNEW that the Diceman, Sam K, and Eddie Murphy would be there, but nowhere to be found. The horror.

  10. On February 10th 2011, WHO THE FUCK WROTE THIS wrote:

    ARE YOU SERIOUS? GTFO…who wrote this?!?!?! Were you trying to attract a larger audience by posting mainstream “comedians” known for anything BUT their controversial material?

    Ohhhhhh, I get it…you’re being controversial by listing people who aren’t controversial in the hopes to start controversy…well played sir, well played.

  11. On February 10th 2011, Joseph Godfrey wrote:

    Jon the yawn Stewart ? He’s never been funny. Watch his old stand-up routines from the 80′s – his talk show that replaced Arsenio Hall back in the day. Hell David Letterman took him under his wing and taught him everything he knows. But still, the funniest thing he’s ever done was getting stabbed in the eye with a pen full of caffeine.

  12. On February 10th 2011, Reynard Fox wrote:

    “No Richard Pryor? Really? …Crap list without Pryor” True, except at number eight, that is not true.

    Dice Clay was a pretty big slip up to miss.

  13. On February 10th 2011, Freebies Link wrote:

    Colbert and Stuart? Come on, those guys aren’t controversial.

  14. On February 10th 2011, GayJesus wrote:

    I agree Diceman should be on here. You shouldn’t limit the list to just comedians who are funny.

  15. On February 10th 2011, Just Kelly wrote:

    Also Dennis Leary. And, lest we forget, the Smothers Brothers managed to lose their tv show because they were so consistently outspoken. Strange to think of them today as so ‘harmless’.

    Kudos on Bill Hicks and Dick Gregory, mind. But am I the only one who thinks Sarah Silverman goes with contraversial material because it’s easier than actually being funny?

  16. On February 10th 2011, Riley Martin wrote:

    Howard Stern (if Kaufman, who was not a traditional stand-up qualifies, so does Howard)
    1. fined millions of $ by the FCC
    2. Incredibly popular for a couple of decades
    3. as well known as nearly anyone n the list and is the type who people either love or hate (or I guess used to love and now hate)

  17. On February 10th 2011, ThatGuy wrote:

    How on earth is Paul Mooney not on this list?

  18. On February 10th 2011, ghosty wrote:

    What? no love for Dave Chappelle?

  19. On February 10th 2011, Lakwak wrote:

    Fluids…Howard Stern is not a comedian. He is a radio host.

  20. On February 10th 2011, CZechmate74 wrote:

    I’m with ya on Bill Hicks all the way.. That dude was a genius. I miss him. but Silverman?? She’s dirty and crass sometimes gross but far from controversial as I would define it.. What about Kat Williams? btw I know why Denis Leary isn’t mentioned… I don’t like him either.

  21. On February 10th 2011, Mark wrote:

    Speaking of blind… you kinda blew right past the controversial aspect, and directly to commenting on a “buddy” movie.

  22. On February 10th 2011, Javier wrote:

    If this list is about CONTROVERSIAL comedians. You can seriously dispose of Colbert or Stweart and give Dave Chapelle the well deserved spot in this list .

    I guess the author aimed for popularity on the list rather than objectivity.

    - @javiwankenobi

  23. On February 10th 2011, Oxen wrote:

    NEIL HAMBURGER. And he is defending his title as I type.

  24. On February 11th 2011, J.T. wrote:

    Good list, but out of order.

    To those complaining about this person or that person not on the list, you aren’t looking at the big picture. Just because you swear, that doesn’t make you controversal. It’s what your words lead to.

  25. On February 11th 2011, A wrote:

    How is Glenn Beck not #1 on this list??

  26. On February 11th 2011, Bob Zmuda wrote:

    Colbert, Stewart and Silverman?
    They are bigger hacks than the author of this piece.

  27. On February 11th 2011, Jeff wrote:

    “But am I the only one who thinks Sarah Silverman goes with contraversial material because it’s easier than actually being funny?” <—-No, you're not. She's terrible.

  28. On February 11th 2011, Mac wrote:

    Most controversial AMERICAN comedians of all time. Certainly unmatched and outstripped when placed on a global list, where only Bill Hicks would make that top 10.

  29. On February 11th 2011, Sexbot wrote:

    Doug Stanhope is more controversial than everyone on this list. look him up.

  30. On February 11th 2011, Guest wrote:

    I was hoping to see Bill Maher on this list.

    Although I like Colbert, this list is a joke for even having him on this. George Carlin not #1 ?

    Just shows that anyone with a blog can make a goofy list and get pageviews.

  31. On February 11th 2011, tdfb wrote:

    Lenny Bruce at #9 behind Silverman, Colbert, Stewert, and Louis CK? No Way!
    Those 4 are funny as hell and very talented but no where as close to controversial as Lenny Bruce…He’s at least in the top 3 and has a great argument for #1

    Bill Maher, Sacha Baron Cohen, Andrew ‘Dice’ Clay, Sam Kinison, Dave Chapelle, Eddie Murphy and tons of less “mainstream” comedians are far more controversial than those 4

  32. On February 11th 2011, Adam wrote:

    Colbert testifying before Congress in character? Ballsier than saying controversial stuff on stage in front of an audience that loves you for it.

  33. On February 11th 2011, Sean wrote:

    Sarah Silverman?? Seriously?? That bitch is as funny as my left toe… she uses “bad” words for “shock” value, because she isn’t funny AT ALL….

    I agree with sexbot, I can’t believe that Doug Stanhope isn’t on this list… that dude pushes the envelope in every fashion, and is funny as hell.

    And while I like Colbert and Stewart, to say that they are in the top 10 controversial comedians of all time?? and above the likes of Pryor and Bruce?? That is just absurd.

  34. On February 16th 2011, ava wrote:

    I just love Richard Pryor and George Carlin…they were the best.

    Just watched the other day some of their videos at http://www.watchstandupcomedy.com/george-carlin-videos and still hilarious after all this time.

  35. On February 17th 2011, Uranus wrote:

    Bill Hicks deserves the award for this. He might have got into n number of controversies and he was proud of that.

  36. On February 24th 2011, Jilly wrote:

    Thats silly…Lolz. Feeling proud for silly reasons.

  37. On May 22nd 2011, Mr Big wrote:

    Good list, but you missed off Doug Stanhope.
    Which is criminal. The man’s a walking nuke.

  38. On May 22nd 2011, nikki wrote:

    Um, where is Bill Maher?

    BTW, I think Jon Stewart is a genius and so is Sarah Silverman. It was nice to see a chick on the list!

  39. On May 29th 2011, wally zebco wrote:

    I or someone else must not know the meaning of CONTROVERSIAL.

  40. On June 4th 2011, Brian wrote:

    Doug Stanhope. Please, will someone give this guy the credit he deserves, just once?

  41. On June 7th 2011, trellis wrote:

    People need to understand that this was a list of the most controversial, not the most offensive/crass. Yes, often times these go hand in hand, but being offensive does not equal being controversial and being controversial does not equal being offensive.

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