Comedians Whose Flops Were Caught On Camera

It's one thing for a comedian to fail at attempting dramatic acting. It's another thing entirely when a comedian falls short at their primary profession — telling jokes and making people laugh. And to be clear, we aren't talking about the occasional joke that falls flat, or a night where the performer and the crowd just never quite got in sync. Comedians aren't expected to absolutely crush every single joke, every single time they're in front of a microphone. And sometimes the vibe in the room is just off, even through no fault of the comedian. 

Instead, we're talking about times where a well-known comedian completely bombed their entire set — and the audience is either completely silent, or they are openly upset at how poor they perceive the performance to be and are intent on letting the comedian know about it. More specifically, these are examples when such moments were actually captured on video, either by someone's own personal recording from the audience or occasions when the comedian was officially being filmed and knew it. 

There are even a couple of instances where a comedian flopped during a televised set — with not only the live audience being openly unimpressed but critics doubling down on the failure of the set in the days that followed.

After beginning his celebrity career as a contestant on several seasons of the MTV reality competition series "Road Rules," Theo Von then shifted gears into stand-up comedy and podcasting. While he has continued to explore other avenues, including game show hosting and a bit of acting, Von has remained primarily known as a stand-up comedian who has released two Netflix specials thus far. In September 2025, while performing at New York City's Beacon Theatre for his forthcoming third Netflix special, Von's set was messy to say the least. 

Those at the show said the comedian appeared to be unprepared, fumbled through his material, couldn't remember his punchlines, and just seemed out of sorts. A fan recorded Von seeming to apologize to the audience for the failed set — though reports say about a third of the crowd left long before then — with the comedian telling fans (via Dexerto), "I'm having a long month, and I'm trying not to take my own life." It raised concerns over Von's mental well-being, with the comedian (at press time) not addressing the incident or clarifying whether he was joking or was indeed struggling with dark thoughts. 

If you or anyone you know needs help with mental health, or is struggling or in crisis, contact one or more of the resources below:

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• Call or text 988 or chat 988lifeline.org.

Sometimes comedy can defuse an uncomfortable situation. That's what happened when Amy Schumer eased the tension after the Will Smith Oscars slap, with a joke that referenced the awkward vibe in the room and allowed everyone to relax a little bit. But comedy can just as often create the uneasy situation to begin with, and Schumer has been at that end of things as well — including an infamous moment when she made Donald Trump jokes in front of the wrong crowd.

During an October 2016 show in Tampa, Florida, Schumer made disparaging remarks about Trump in the lead-up to that year's presidential election. Though the people at the show had chosen to be there and surely had to have been aware of Schumer being an outspoken Hillary Clinton supporter, many of them still began booing in response to Schumer's Trump jokes. Rather than just moving on, Schumer's entire act got derailed as she asked the audience to point out the people who were booing and attempted to have them thrown out. 

Things got even more unwieldy when Schumer brought one of the booing audience members up on stage to ask him why he voted for Trump. When he expressed his distrust of Clinton, the audience erupted in cheers and applause, further cementing the fact that the crowd was definitely not on Schumer's side. In the end, around 200 people ultimately walked out of the trainwreck set, footage of which was obtained by Inside Edition from an audience member. 

Dave Chappelle is the type of person who has always known exactly the type of artist he wants to be. He's never been afraid to pass on opportunities that would mean big things for his career, including turning down the role of Bubba in "Forrest Gump" because he felt it leaned too hard into certain stereotypes of Black characters. He also famously walked away from his popular — and extremely well-paying — Comedy Central show simply because he didn't like where it was headed creatively.

One of the things that people love about Chappelle's comedy is that it's often very unpolished and off the cuff, with the comedian at least seeming like he's just up on stage winging it. Of course, much of that is probably a lot more planned out than it appears, with Chappelle making it seem more loose and improvisational than it actually is. Sometimes, however, he gets a little too loose and comfortable for his own good, leaving the audience bored, restless, and disappointed. Which is what happened during Chappelle's infamous 2015 set at the Fillmore Detroit theater, as documentated on an audience member's phone. 

In the video, Chappelle goes long stretches of time saying literally nothing at all, with the clearly restless audience shouting at him to talk. Things get so bad that audience members start shouting generic joke setups in hopes that Chappelle will deliver a punchline, or just say anything at all. People who were at the show said the comedian spent the majority of his set mumbling and appearing out of it, with many seeking refunds for what one fan said felt more like a press conference than a comedy show. 

While he's better known these days as a frequent fixture in the films of Adam Sandler, Nick Swardson was a stand-up comedian first. He continues to perform, having released a number of comedy specials and albums throughout his career, and was still at it as recently as 2024. However, he had a particularly notorious show that year that went so badly the venue's staff had to escort him off stage before the set was even over.

The show in question took place in Beaver Creek, Colorado in March 2024. According to attendees, and confirmed by multiple fan videos, Swardson quickly got off on the wrong foot with the crowd. Once the audience began turning on him, Swardson made no effort to win them back and instead just got confrontational with his fans. Only 20 minutes after Swardson's set began, things had already gotten so out of control that event organizers turned off his spotlight, cut his mic, and removed him from the stage.

The next day, after news of the debacle went viral, Swardson acknowledged the incident on X and blamed a combination of alcohol, edibles, and Colorado's high altitude for his behavior. The venue subsequently contacted ticketholders via email to inform them that they'd be receiving a full refund for the botched event. 

Comedians are typically pretty open about the fact that they bomb from time to time. Many of them tell bombing stories on podcasts and during interviews, and some even discuss them within their acts. In the case of Pete Holmes, he has an example of a night that he not only delivered a total dud of a comedy set, but is fortunate enough to have the footage of — which he even shared it to his own social media accounts and YouTube channel.

What's even more admirable about the fact that Holmes shared the footage is that the set in question wasn't even from that long ago at the time. He posted the video in 2006, only four years after it happened in 2002. Comedians tend to want a fair amount of distance from a bomb night before they are able to joke about it, and definitely like to wait until they have already reached massively successful status. Given that Holmes arguably wasn't a household name until the 2010s, he gets a lot of credit for already being willing to be self-deprecating about his bad sets before he was even hugely famous.

As for the set in question, it occurred in Peoria, Illinois — and apparently, Holmes didn't play in Peoria that night. The footage contains four and a half of minutes of Holmes telling jokes that either get awkward chuckles, or no laughs at all, punctuated by Holmes splicing in memes and adding various effects to accentuate just how poorly the crowd was reacting to the material. 

Now we turn from a stand-up who voluntarily shared a video of himself bombing to one who seemingly did all he could to have a video of him flopping scrubbed from existence. In February 2013, actor and comedian Rob Delaney appeared as a guest on "Jimmy Kimmel Live," where he did a comedy set. It's truly awkward to watch, as the studio audience barely chuckles through the majority of Delaney's routine — and talk show audiences are nothing if not overly generous with laughter and applause, making the silences all the more jarring.

In the weeks that followed, something odd happened: Several websites, as well as a number of people on social media, pointed out that videos of the set seemed to have vanished from the internet, after having previously been made officially available. Comedian Daniel Tosh even claimed the same on his own show, accusing Delaney of having the set taken offline. Various people who uploaded their own copy of the footage to their own YouTube accounts also claimed to have had those videos subsequently taken down, seemingly suggesting an especially aggressive effort to make the episode unavailable to watch at all.

There has never been any official confirmation that Delaney or anyone associated with "Jimmy Kimmel Live" ever had anything to do with the video being hard to find for a while. Things eventually died down, and it's no longer difficult to find the footage, so you can now see for yourself the disastrous set that Delaney — allegedly — tried to scrub from the internet. 

Shane Gillis almost had a different route to fame. In 2019, he was hired as a new writer and cast member for "Saturday Night Live," which would have raised his profile significantly. But he never actually made his official "SNL" debut, as he was fired before his first episode when videos of him making racist and homophobic jokes on his podcast went viral. Instead, he used the incident as an entry point into railing against wokeness and political correctness in comedy, an approach that brought him mainstream fame as a comedian even without having any "SNL" screen time.

Gillis got so famous, in fact, that "SNL" gave him another chance in March 2025 — only this time, he was asked to host. It certainly must have felt vindicating to Gillis. However, rather than use the moment to deliver a hilarious monologue and make "SNL" feel sorry for rejecting him, Gillis opened the episode with a set that fell completely flat. Things got so bad that Gillis himself acknowledged how poorly things were going multiple times. At one point, he seemed to suggest that "SNL" having a liberal vibe was to blame for why he wasn't getting laughs — the whole tired "if you don't think it's funny, you must just be too sensitive" refrain. 

Even worse, after a long set up that the audience clearly wasn't taking the ride with him on, Gillis flat out admitted that he wished he could just abandon the joke entirely. At that point, both the studio audience and the viewers watching at home were wishing the same thing. 

The late Gilbert Gottfried was always one of those comedians who sometimes went too far — but that was part of his shtick. He was the type of performer who reveled in his keen ability to make an audience uncomfortable and to push boundaries. When he tweeted a joke so offensive that he lost a cushy longterm gig as the voice of the Aflac insurance goose, it's possible he regretted dabbling in bad taste in that particular instance. But despite the joke in question poking fun at the lives lost during Hurricane Katrina, that wasn't even the first time Gottfried mined a major American tragedy for comedy material.

It hadn't even been three weeks since the terrorist attacks of September 11, 2001 before Gottfried found himself at the Friars Club roast of Hugh Heffner. When the comedian decided to make a joke about his flight having a layover at the World Trade Center, the audience wasted no time in groaning and booing him, in addition to audible cries of "too soon!" For what it's worth, Gottfried hadn't exactly had the audiences in stitches prior to that. In his defense, trying to put on a celebrity roast the same month that 9/11 occurred, and not knowing how funny or how edgy to be, was uncharted territory. 

It was an uncomfortable night all around, for everyone involved. But Gottfried deciding to not only address the elephant in the room but violently body slam it definitely wasn't the way to go. 

Considering that "Son of the Mask" — the superhero comedy that ruined Jamie's Kennedy's career — had been released two years prior, one would think he would have just been happy to have a paying gig. Yet, when Kennedy hosted a press event for the Electronic Entertainment Expo (E3) in 2007, he spent the entire time acting like the job was beneath him and that he couldn't wait to be done with it. Why he was in such a hurry remains a mystery, since his 2007 dud "Kickin' It Old Skool" was the only other job he had going at the time. 

Other than acting utterly bored by the whole thing, Kennedy decided that hosting a press event for the video game industry meant that he should tell nothing but wall-to-wall jokes about how lame people who play video games are. And we aren't talking clever, good-natured roasting, either. Instead, Kennedy went with the lowest common denominator and talked about how gamers have bad personal hygiene, never go outside, still live in their parents' basements, and so on. 

Picking on nerds like a bully from a bad 1980s teen comedy didn't exactly endear Kennedy to the crowd at the event, who met the majority of Kennedy's material mostly with dead silence. Even professional skateboarder Tony Hawk, who is generally known for being a friendly, affable guy, struggled to smile and be polite while being interviewed by the pretentious Kennedy, with his continual barrage of jokes at the expense of literally everyone at the event that wasn't him.

A bad set by an already established comedian very rarely kills their entire career. Certainly there have been instances where a hugely famous comedian says some things that get them in hot water, and maybe even costs them films or TV shows. But they are almost always still able to continue doing stand-up comedy if they so choose — it may be the only career in which one can't get canceled, for better or for worse.

In the case of Michael Richards, he had a night onstage that was so disastrous and so damaging to his reputation that the public has barely heard from him since. In 2006, amateur video of Richards going on a racist tirade during a set at The Laugh Factory set the internet ablaze. Released by the then-recently launched gossip site TMZ, Richards is seen confronting hecklers by first noting that they're Black before proceeding to repeatedly call them racial slurs and making other racially charged remarks both directly at them and just in general. As Richards and the hecklers verbally spar, a number of people can be seen getting up and leaving, before Richards himself finally exits the stage as well without saying a word. 

After a mini-apology tour, Richards largely retreated from the public eye for many years, though he continued to occasionally pop up in shows like "Curb Your Enthusiasm" and "Comedians in Cars Getting Coffee." In the fall of 2025, close to 20 years after the incident, Richards finally returned to the stage for the first time since 2006 for a live Q&A tour — though, notably, it is not billed as comedy.