10 Most Controversial Guests On Late Night TV, Ranked

Late night talk shows aren't typically a place you'd expect to find controversy. Historically, they've been a destination for feel-good content that sees us off to Dreamland. We tend to reserve the more touchy subjects for daytime television. But every now and then, the late-night TV world is rocked by serious backlash from a controversial guest, such as when Conor McGregor appeared on "The Tonight Show Starring Jimmy Fallon" in 2026 after losing a sexual assault case pertaining to a 2018 incident. 

Typically, talk show guests range from big-time Hollywood stars running the media circuit for their latest movie to piping hot pop stars, sports stars, authors, and other public-facing figures. A handful of friendly softball questions later, and we've all had a few good laughs and learned a little something at the same time. What better place for someone in the public eye to try and rehab their image after stepping face-first into a mess of their own making? 

If we've learned nothing from the era of cancel culture, it's that backlash generates plenty of engagement. From a shock jock to comedians who went too far and even a reality star-turned-politician, these 10 controversial talk show guests, ranked by public outrage, certainly generated that. 

Considered one of history's most legendary comedians, Andy Kaufman got his start performing in small New York comedy clubs circa 1972. He later appeared on shows like "Dean Martin's Comedy World" and "Saturday Night Live," where viewers voted him off the show for a bit that was ahead of its time and left contemporary viewers baffled and enraged.

Known for his surreal Dadaist comedy style, Kaufman was fond of absurd, over-the-top alter-egos like Foreign Man, a persona that evolved into Latka on the 1978 sitcom "Taxi." He was particularly enamored of his kayfabe alter-ego "the foremost male wrestler of women in the world," a persona so convincing that many struggled to comprehend whether it was a bit at all. As reported in The Victoria Advocate's December 21, 1979 issue, each of his "SNL" appearances generated its share of angry letters. It was this persona Kaufman presented on 11 separate"Late Night With David Letterman" appearances, angering almost as many viewers as they delighted.

When the audience caught the gag, he awkwardly doubled down. During Kaufman's February 17, 1982 appearance, the comedian shared a clip of his recent professional wrestling appearance, announcing, "It started as a joke and now people are taking it so seriously ... so I've started wrestling in professional arenas." In 2025, documentarian Jenifer Westphal told People, "I don't know if Andy saw a clear difference between himself and the characters ... he was the character, and the character was him."

Understanding the feud between Jimmy Kimmel and Kanye West requires unearthing 2013 lore that has since become pop culture obscura against the furious pace of today's news cycle. But at the time, the whole thing led to serious controversy culminating in West's appearance on Kimmel's show.

The drama began after Kanye declared himself "the number one rock star on the planet"  on BBC's Radio 1.  Kimmel parodied the interview using children with milkshakes on "Jimmy Kimmel Live!," incensing Kanye. In a now-deleted Twitter thread preserved on a Reddit post, West's cringe-inducing post towards Kimmel, in dramatic all-caps, read, "SHOULD I DO A SPOOF ABOUT YOUR FACE OR YOU F***ING BEN AFFLECK ... #NODISRESPECTTOBENAFFLECK #ALLDISRESPECTTOJIMMYKIMMEL!!!!"

After good-spiritedly telling his audience during his opening monologue (via People), "Finally, I'm in a rap feud," Kimmel revealed Kanye had called to threaten him and demand an apology. Kanye's subsequent appearance sparked controversy at the time from viewers who thought the feud was all a big publicity stunt. But as the pair would confirm, it was all a sincere misunderstanding. To clear the air, Kimmel had Kanye guest star, explaining the real reason he'd parodied Kanye's interview was because "I like to hear kids curse." For his part, Kanye confessed he'd unloaded all of the negativity he'd harbored against people who "treat celebrities like zoo animals, acting like ... their life is not serious"  on Kimmel.

Long before her own show on conservative streamer Fox Nation, Tomi Lahren honed her skills as a prolific rage-baiter on Glenn Beck's paid TV network TheBlaze. Lahren was catching backlash as early as 2013, when her criticism of Beyoncé's halftime show led to the singer's fans vandalizing the pundit's Wikipedia page. And in a dirty deleted tweet reprinted in People, the pundit drew ire by writing, "Meet the new KKK, they call themselves 'Black Lives Matter' but make no mistake their goals are far from equality. #Dallas #bluelivesmatter." So when "The Daily Show" host Trevor Noah invited Lahren on as a guest in 2016, many were outraged. 

Still, Noah saw having Lahren on the show as a step toward healthy discourse. In a Between the Scenes clip, Noah explained, "I love having discussions with people I know I don't agree with and they don't agree with me ... otherwise, you get trapped in a bubble where you're just talking to people who agree with you." 

But many saw Noah as platforming and normalizing bigotry. Buzzfeed's Tomi Obaro criticized Noah for espousing a "wan, trite call to moderation that works as a book promotional strategy." In the same Between the Scenes clip, Noah revealed that Lahren had earned a spate of obscene, graphic assault and death threats from people claiming to be "Daily Show" fans.

Hollywood power couple Blake Lively and Ryan Reynolds have been embroiled in controversy since late 2024, when scandal surrounding Lively's film "It Ends With Us" caused their reputations to fall off a cliff. Once considered two of the world's most beautiful people, they seemed at the zenith of their power in August 2024, when Reynolds' "Deadpool v. Wolverine" and Lively's "It Ends With Us" released around the same time. 

Lively started taking heat for claims that her film was portraying domestic abuse themes as a romance. At the same time, the rumor mill heated up about Lively's falling out with co-star and director Justin Baldoni. Things only got worse from there when salvo after salvo was fired between the film's romantic leads. Lively accused Baldoni of sexual harassment, creating a hostile workplace, and an elaborate conspiracy to destroy her and Reynolds' reputations. In turn, Baldoni accused Lively of wrongful civil extortion, defamation of character, and invasion of privacy. The fact that both sides saw various charges thrown out of court helped neither party — let alone the abuse-themed romance starring both of them.

Public sentiment turned against Lively, who was accused of falsely crying victim to leverage public opinion. The response to her appearance on "Late Night With Seth Myers" in the middle of this mess was so intense producers shut down comments on YouTube.

Howard Stern and Jay Leno's long-running beef originated with Stern's 1995 appearance on "The Tonight Show With Jay Leno." Stern was always fond of pushing the boundaries of both free speech and polite society. For context, he drew controversy for playing gunshots over the music of recently-deceased Mexican-American pop star Selena Quintanilla-Pérez that same year. Three years earlier, Stern was fined by the FCC for making lewd comments about controversial pancake icon Aunt Jemima. So it's hard to fathom what Leno, generally a purveyor of family-friendly content, was thinking when he booked the radio star.

Stern, there to promote his book, walked onto stage flanked by two adult entertainment stars clad in pink bikinis as a wildly excited audience screamed in delight. Seconds in, Stern was insulting former "Tonight Show" bandleader Branford Marsalis and poking jabs at Leno's ratings, and it only went downhill from there. Claiming he wanted to help Leno achieve his record ratings, Stern incited the women to kiss before spanking one of them, asking, "Has daddy's girl been a bad girl?" Appearing increasingly uncomfortable, Leno told Stern it would "all be edited out." Stern's antics continued after famed film critics Gene Siskel and Roger Ebert came onstage, allegedly involving toe-sucking.

NBC put out a statement decrying Stern's behavior, and Leno later called Stern's show to complain. Although Leno has refused to continue engaging, Stern still takes every opportunity to spew anti-Leno venom.

Famed Irish mixed martial arts UFC fighter Conor McGregor blew the world away with his powerful punches. Compact, powerful, and intense, the charismatic McGregor's rapid ascension to stardom generated a whopping $1 billion in pay-per-view buys. But by the time he appeared on "The Tonight Show Starring Jimmy Fallon" in 2026, McGregor had serious public image problems including a civil rape case he lost. In his 2015 interview with McGregor, Esquire's Chris Jones wrote, "Most of our social interactions are based on the premise that we've all agreed to follow certain rules. McGregor has not agreed to those rules ... which is unnerving because it makes his behavior unpredictable." 

Jones' comments unfortunately proved prescient when McGregor was caught on camera shattering a bus window with a hand dolly in 2018. Between 2018 and 2019, he was investigated for two sexual assault charges, one eventually leading to the civil lawsuit wherein McGregor was accused of rape at a Dublin hotel. He was booked for robbery after smashing a fan's phone in 2019, spent two days in French Corsican jail over sexual assault allegations in 2020, was accused of assaulting and threatening to drown a woman that same year, and received further sexual assault accusations at the 2024 NBA finals. 

Fallon's platforming of McGregor drew scathing criticism, as reflected in the YouTube comments for the interview. Summing up the public outcry, one incisive viewer wrote, "At this point invite Diddy too."

These days, a world where now-President Donald Trump was a hammy reality TV star making semi-regular talk show appearances feels like an alternate reality. But by the time he made his first presidential bid in 2016, Trump had long-since metamorphosed into a divisive populist showman. When Jimmy Fallon hosted the MAGA leader during campaign season on "The Tonight Show," the intense response left the talk show host reeling. Many even cited Fallon as playing a key role in Trump's victory, putting a friendlier face on authoritarianism and xenophobia.

Known for his easygoing and lightweight interview style, Fallon kept the vibe of Trump's interview friendly, even tousling Trump's hair at one point. In a list of reprinted tweets on The Hollywood Reporter, one critic wrote, "@KatyTurNBC I will never watch Jimmy Fallon again. That's how strongly I feel about humanizing a monster." Another wrote, "Jimmy Fallon unfortunately just showcased a potential dictator on his show and made him like 'just another guy.' Except he's not."

While he later joked about it in his interview with Democratic presidential candidate Hillary Clinton, privately, the public reaction was harder for Fallon to stomach. In 2017, he confessed to The New York Times that he had to step back from using social media and watching the news. "They have a right to be mad," Fallon admitted. "If I let anyone down, it hurt my feelings that they didn't like it. I got it."

Viewers who grew up watching "Seinfeld" watched their enjoyment of the show fizzle out in the aftermath of Cosmo Kramer actor Michael Richards dropping a racial slur onstage in 2006. And just as his public drop-off would herald a new dawn of cancel culture, Richards' apology on "The Late Show With David Letterman" was a prototype for countless half-hearted apologies to come.

It began when Richards was performing at the Laugh Factory. Richards had a full-blown meltdown when a Black audience member heckled him, turning his ire on the man and several other audience members in a racial slur-infused tirade. Richards would later recall on The View, "I'm on stage with a microphone in my hand doing an act, breaking in materials late at night, and a man in the audience made an announcement: I'm not funny. He doesn't think I'm very funny, and I came back."

The backlash had been fierce and swift. In a desperate bid to salvage Richards' reputation, Richards accompanied Jerry Springer on Letterman to apologize. Speaking from Hollywood, Richards pled, "I got heckled and I took it badly and went into a rage and said some pretty nasty things to some Afro-Americans, a lot of trash talk." When the audience chuckled, Seinfeld called them out, chastising, "Stop laughing, it's not funny." Richards, whose career was effectively halted with the incident, later quasi-retconned the incident, claiming he'd actually gone into character at the time.

Another offensive early 1990s comic, Andrew Dice Clay was known for his hypermasculine, trash-talking, misogynist-leaning Italian-American persona. Audiences couldn't get enough of his intentionally offensive speech, much to the chagrin of many LGBTQ+ rights groups. "They're on TV every day, 'we want our rights, we want our rights,'" Clay's act went. "I'll give 'em rights — 10% off of Vaseline, now get the f*** back in the closet."

The blue comic was incredibly controversial by the time he appeared on "The Arsenio Hall Show," with two guests boycotting "SNL" after Clay had been scheduled to appear in 1990. The reaction to Hall's show had been similar, with house keyboard player Starr Parodi boycotting the episode in protest. When Clay's movie "Dice Rules" came out in 1991, the 200-outlet Loew's theater chain refused to show it citing Diceman's treatment of women.

Perhaps sensing the winds of change, the third of Clay's "Hall Show" appearances saw him claim that his  persona had always been intended as parody, telling Hall, "I try to show how stupid the racism is." When Clay went on to joke comparing a "white disco" to a "cerebral palsy contest," Hall called him out on it for using members of the disabled community as fodder for his self-professed satire, to which Clay claimed good comedy should target everyone. Addressing LGBTQ+ protestors, Clay emphasized that he had stopped doing gay jokes because of the AIDS crisis.

Late night talk show guests don't get more controversial than one of the world's most infamous cult leader-serial killers. Tapping into general audiences' mix of revulsion and fascination at a 1981 press conference promoting the 53-minute interview, one journalist understandably queried why anyone would platform such a monster. As recounted in the Washington Post, Snyder had not gotten far into the press conference before stating that they would have likely done the same if given the opportunity to interview Manson.

Before the interview, Snyder acknowledged, "Some people might ask why run the Charles Manson interview. Well, television is supposed to make us look at ourselves, and that goes beyond picturing all of us as normal and rational people who are suddenly shocked when the time bomb of insanity goes off." To refuse to air the interview, Snyder asserted, would be tantamount to ignoring the issues.

What followed was not, as many might have expected, a foray into the mind of a villain. The interview, a chaotic discourse consisting mainly of Snyder's pleas for confession and Manson's mind-numbing, profanity-laced tangents, instead showed the world something infinitely more complex and troubling.