In October 2023, comedian Anthony Jeselnik appeared on the podcast “This Past Weekend,” which is hosted by fellow comedian Theo Von. At one point in the conversation, Jeselnik took aim at comics who focus more on offending people than actually being funny. “This is a quote attributed to Andy Warhol that I love, it’s, ‘Art is getting away with it,'” he explains. “If you put out a special, and everyone’s pissed … you didn’t get away with it. You need to make everyone laugh.” 

Of course, there are plenty of instances where comedians failed to make everyone laugh. They may see themselves as speaking truth to power when in actuality their statements were incredibly bigoted. In other instances, comedians realized some past jokes weren’t as insightful as they may have believed they were years ago, or perhaps a comedian simply existed during an era that wasn’t ready to hear what they had to say. As much as they may want to claim they’re simply jokes that people shouldn’t take seriously, words have immense power, especially when they’re coming from celebrities with huge platforms. 

For as long as there have been jokes, there have been jokes that have gone too far. These are just some of the comedians over the years who landed in hot water for their controversial bits. 

On October 27, a little over a week before the 2024 election, Donald Trump held a rally at Madison Square Garden that was filled with speakers providing inflammatory remarks. However, the one statement that broke through the most came from comedian Tony Hinchcliffe. He made many racist jokes and even earned the ire of Taylor Swift’s fans for inferring that her boyfriend Travis Kelce could be the next O.J. Simpson. But his most infamous statement came when he referred to Puerto Rico as a “floating island of garbage.” 

The comment sent waves throughout Hispanic communities throughout the United States. The joke seemed particularly ill-suited, considering how many Puerto Ricans live in swing states like Pennsylvania. Latin celebrities like Bad Bunny and Jennifer Lopez even came out in support of Kamala Harris after Hinchcliffe’s comments went viral. And it wasn’t just Democrats who had issues with the set. Rick Scott, a Republican senator from Florida, posted on X (formerly Twitter) after the event, “This joke bombed for a reason. It’s not funny and it’s not true. Puerto Ricans are amazing people and amazing Americans!”

Rather than apologize or offer any semblance of self-reflection, Hinchcliffe doubled down on his “joke” following the backlash, writing on X: “These people have no sense of humor … I made fun of everyone.” Hinchcliffe’s set would’ve been awful even if it was done at a comedy club. But performing such material at a political rally only serves to further stoke the flames of hatred dividing the country. 

The following slide contains references to domestic violence.

Matt Rife seemingly came out of nowhere … assuming you aren’t on TikTok. He first got big on that platform self-publishing bits from his comedy shows, mostly engaging in crowd work. He gained a substantial following, and it wasn’t long until Netflix gave him his own comedy special in 2023, titled “Natural Selection.” The only problem was that he immediately began this special with a joke about a female server with a black eye helping his table. 

The special also contained homophobic jokes and seemingly plagiarized bits from the late Ralphie May. But it was Rife’s domestic violence joke that earned the most ire. “Natural Selection” has an abysmal 19% audience score (with over 500 reviews counted) on Rotten Tomatoes, and the offensiveness didn’t end there. Rife posted a response to his Instagram Stories, asking people to click a link if they were offended by his material. The link directed users to a website offering a protective helmet for special needs children. 

Perhaps the reason the domestic violence joke made headlines is because Rife’s initial online fan base consisted largely of women. Him joking about a female victim of domestic violence was seen as turning his back on the people who helped make him famous in the first place so that he could appeal to more male sensibilities. The controversy didn’t deter Netflix from working with Rife again for another comedy event, “Lucid — A Crowd Work Special.”

If you or someone you know is dealing with domestic abuse, you can call the National Domestic Violence Hotline at 1−800−799−7233. You can also find more information, resources, and support at their website.

There are plenty of Kramer moments Michael Richards ad-libbed on the “Seinfeld” set, but during a now infamous 2006 set at The Laugh Factory, Richards probably wishes he had stuck to his prepared material. During a performance, captured on blurry video, Richards calls out some hecklers and calls them the N-word. The backlash was swift, and shortly after, Richards appeared on “Late Show With David Letterman” to apologize for the outburst. But the damage was done. 

It’s been nearly two decades since the incident, and Richards’ career never fully recovered, although it appears as though he doesn’t have much interest in going back to his “Seinfeld” glory days. His acting roles have been few and far between, mostly working with former “Seinfeld” co-stars in projects like “Bee Movie” and “Curb Your Enthusiasm.” In 2024, he spoke with People about his upcoming memoir, “Entrances and Exits,” and he definitively declared, “I’m not looking for a comeback.”

He also discussed doing some lengthy introspection over the years to help the damage within himself that prevented from feeling like he was ever good enough, even with all his success in the entertainment industry. Richards continued, “I have nothing against Black people. The man who told me I wasn’t funny had just said what I’d been saying to myself for a while. I felt put down. I wanted to put him down.”

The Laugh Factory in Los Angeles has been the site of many controversial stand-up moments over the years. In 2012, just days after the horrific Aurora, Colorado shooting during a screening of “The Dark Knight Rises,” Dane Cook took to the stage to talk about how much he didn’t like the film. He concluded by saying, “I know that if, ya know, none of that would have happened, I’m pretty sure that somebody in that theater, about 25 minutes in, realizing that it was a piece of crap, was probably like ‘Ugh, f***ing shoot me.'”

With 12 people dead and dozens of others injured, many didn’t think it was appropriate to joke about the tragedy, especially so soon after it had occurred. Cook later posted an apology on Twitter (via The Wrap): “I am devastated by the recent tragedy in Colorado & did not mean to make light of what happened. I made a bad judgment call with my material last night & regret making a joke at such a sensitive time.”

Hollywood won’t cast Dane Cook anymore, but his “Dark Knight Rises” joke is really only a small factor in that. From leading movies that became box office bombs to accusations of stealing other comedians’ jokes, a lot of people don’t seem to want anything to do with Cook these days. 

The following slide contains references to sexual assault.

In 2017, during the #MeToo movement, Louis C.K. faced numerous accusations from women accusing him of sexual misconduct. His reckoning was swift, with Netflix cancelling a planned Louis C.K. stand-up special and his film, “I Love You, Daddy,” which he wrote, directed, and starred in, remaining unreleased. However, before all of this, C.K. regularly found himself towing the line of good taste, and that includes a 2015 “Saturday Night Live” monologue where the comedian made light of pedophilia. 

The response from the crowd that night was the tip-off that the joke wasn’t going to go over well. Amid some nervous laughs, C.K. stated, “How do you think I feel? It’s my last show, probably.” Amazingly, that wasn’t his last show, as he’d return to host “SNL” again in April 2017, right before those sexual misconduct allegations against him came to light. 

Plenty of folks came forward on social media to condemn the jokes while others insisted that this is simply what comedians do — push boundaries. Louis C.K. made a career out of telling offensive jokes, and even his more formal cancelation couldn’t stop him. Following #MeToo in 2017, C.K. continued releasing stand-up specials through his website, and he even sold out Madison Square Garden during a 2023 performance. Even with so much baggage, he still has a surprising amount of support from fans. 

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN’s National Helpline at 1-800-656-HOPE (4673).

There are certain subjects comedians should probably avoid if they want to avoid controversy — politics, religion, and Taylor Swift. Nikki Glaser learned that the hard way when a stand-up clip of her was featured in Swift’s documentary, “Miss Americana.” Prior to “The Eras Tour” movie blowing away the box office, Swift unveiled this intimate portrait of dealing with fame and all the insecurities that come with it. At one point, Glaser says the following during one of her acts: “She’s too skinny. It bothers me. All of her model friends — and it’s just like, c’mon.”

The statement is paired with other criticisms from members of the media lobbied toward Swift that made her self-conscious and want to back away from the spotlight. Following the film’s release, Glaser posted a lengthy statement on Instagram apologizing for the comments: “I really have no need to post this other than to apologize to someone who seriously means SO much to me. I only got a couple death threats from die-hard Swift fans, which as one myself, I totally get.” Amazingly, the message reached Swift, who accepted it while discussing the importance of showing how people can grow. 

And it appears the incident hasn’t hampered Glaser’s enthusiasm for being a Swiftie. In September 2024, she claimed to having seen Swift perform 18 times over the span of 15 months. That’s some serious dedication. 

Comedy Central Roasts are known for being exceptionally crude and vulgar. It’s a no-holds-barred joke fest where presenters often push the boundaries of good taste. Most of the time, everyone takes the jabs in good stride, but Jeff Ross, a fixture at these events, took things a step too far at the 2015 Roast of Justin Bieber when he joked about Fast & Furious star Paul Walker’s passing.

The Fast & Furious cast was never the same after Walker died in November 2013 after he collided a vehicle into a tree. Ross made a reference to Walker when comparing him to Bieber’s driving abilities and then landed another one while referencing his franchise co-star Ludacris, who was in attendance. Immediately, it was clear Ross had gone too far, as the audience groaned after the comment, to which Ross replied, “Too soon? Too fast? Too furious?” At a press briefing following the taping of the roast, Bieber himself said he didn’t particularly care for the Paul Walker jokes.

Roasts frequently have groan-worthy moments, but this one was so bad, Comedy Central actually axed it from telecasts. These roasts have had other jokes about people’s deaths over the years, like making light of Ryan Dunn’s death in front of his “Jackass” co-star, Steve-O, but it’s clear this one crossed a line. 

The following slide contains references to sexual assault.

For good reason, rape is seen as something that should never be joked about. Perhaps that makes it even more enticing for comedians to joke about to see what they can really get away with. Even George Carlin had a bit about the subject, but that doesn’t mean comedians don’t regularly land in hot water by making light of sexual violence. 

That’s precisely what Daniel Tosh learned after a 2012 set at The Laugh Factory. Tosh apparently made a series of jokes surrounding sexual assault, prompting a woman in the audience to express how such jokes are never funny. Tosh then alluded to that woman getting sexually assaulted right then and there, and the internet exploded into a series of thinkpieces about whether Tosh crossed the line. 

Many comedians came to Tosh’s defense, essentially asserting that while they may not agree with that specific joke, they believe comedians should be allowed to explore dark subjects in the name of humor. Still, many claimed this subject is just too painful to joke about. Roxane Gay wrote this for Salon: “Rape is many things — humiliating, degrading, physically and emotionally painful, exhausting, irritating. It is never funny for most women.” Tosh apologized for the set, and it serves as a reminder that if the job of a comedian is to make people laugh, certain subjects should probably remain out-of-limits. 

If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN’s National Helpline at 1-800-656-HOPE (4673).

In the world of comedy today, there’s a lot of chatter about what people can still joke about. Accusations of cancel culture run rampant, often proclaimed by comedians on their Netflix stand-up specials where they talk about how they’re being silenced. And while cancel culture remains a nebulous subject with unclear boundaries of what it even means to get canceled, some comedians faced actual repercussions for stand-up sets. 

George Carlin remains one of the most legendary comedians in history, and one of his most famous bits involves the “Seven Words You Can’t Say on Television.” In 1972, Carlin performed at Milwaukee’s Summerfest, where he did the profanity-ridden material, and once his performance was over, he was arrested over disorderly conduct charges. Of course, the charges were ultimately dropped, seeing as they were protected by the right to freedom of speech. 

TMJ4 News spoke with Carlin after the controversy, who explained, “There are 400,000 words in the English language, and there are seven that right now I can’t say to you … I find it kind of funny to be hassled for using them when my attention is to free us from hassling people for using it.” Carlin passed away in 2008, but his legacy as one of our most revered stand-ups remains intact.

Lenny Bruce’s shocking routines (at least for the time) predate George Carlin. Throughout the 1950s and ’60s, he performed around the United States, often engaging in shocking material that would later lead to numerous arrests. One such incident occurred in San Francisco in 1961, when he was arrested for using a slur rooted in homophobia. 

Bruce faced similar arrests in Los Angeles, Chicago, and New York City. While charges elsewhere would get dismissed, Bruce went to court in New York over violations of obscenity laws. He was convicted in 1964 and sentenced to four months of being in a workhouse. He tried to appeal, but he ultimately died before that could happen. In 2003, 37 years after the conviction was handed down to him, he received a posthumous pardon. 

Lenny Bruce is held in high regard from comedians these days as a pioneer who pushed boundaries and faced actual consequences for the sake of his art. It’s only a shame Bruce didn’t live long enough to see this reappraisal of his material, as he paved the way for comedians to try out shocking material in the decades that followed.