The late-night talk show isone of the last remnantsof a bygone era of television. A pre-social media platform allows viewers to learn a little more about their favorite performers as they share off-the-cuff anecdotes with trusted late-night hosts. The after-hours broadcast implied anything could happen–like the audience is invited to a midnight party in the Hollywood Hills.
The reality is, unless noted otherwise, episodes of late-night talk shows are filmed in the middle of the day with all the rough edges edited out before broadcast. The off-the-cuff conversations aren’t outright scripted, but usually planned and agreed upon.The seemingly spontaneous nature of the late-night format is the result of a tightly calibrated operation, so when the following guests decided to go rogue, their appearances were nothing short of controversial.
10Joaquin Phoenix (June 25, 2025)
‘Late Show with David Letterman’
ActorJoaquin Phoenixappeared onLate Show with David Lettermanto promote his new film,Two Lovers, but didn’t arrive in the mood to talk. Hair disheveled, and hiding behind a large beard and sunglasses,Phoenix seemed uncomfortable and reluctant to make eye contact.HostDavid Lettermanaddresses the announcement that Phoenix would be quitting acting, saying he hopes the actor will reconsider after some time off, but Phoenix only fidgets in his chair and mumbles a reply. Phoenix tells Letterman he’s leaving acting to pursue making hip-hop music, eliciting a laugh from the crowd that irritates theJokeractor. Eventually, Phoenix’s one-word replies cause Letterman to laugh at the awkward interview, and near the end, famously quips, “Joaquin, I’m sorry you couldn’t be here tonight.”
Media speculation about the mental health of Phoenix was in full force after the interview aired, along with curiosity about the new music career. Later,the whole thing wasrevealed to be a hoax, and the late-night appearance was a part of directorCasey Affleck’supcoming movie,I’m Still Here. The film would be a mockumentary chronicling Phoenix’s transition from acting to music while attempting to explore the trappings of celebrity culture. Phoenix would return to Letterman’s show roughly a year later and apologize to the host, making it clear Letterman was not in on the joke.
Late Show with David Letterman
Late Show with David Lettermanis not currently available to stream in the US.
9Andy Kaufman (July 12, 2025)
‘Late Night with David Letterman’
Still in the throes of his wrestling career,Andy Kaufmanagreed to be onLate Night with David Lettermanwith his on-screen rival,Jerry “The King” Lawler.Kaufman and King recently “fought” one another, and this would be the first time they would be face to face since the match. Kaufman appears in a neck brace and initially stays calm while King insults him, but once it’s clear King doesn’t intend to give Kaufman the apology he came for, the conversation grows heated.King eventually stands and slaps Kaufman out of his chair, sending the remainder of the segment into a profanity-laden verbal assault from Kaufman until it almost becomes violent for a second time.
Letterman didn’t miss a beat during their exchange, firing one-liners with precisely perfect timing while the chaos unfolded. That is, unless the chaos was planned. Without delving too far into conspiracy theory territory, professional wrestling is a pre-determined sport, meaningKaufman and King were working togetherduring their wrestling rivalry, and would assumably be doing the same thing on Letterman as well. The fighting may have been another calculated stunt to sell wrestling tickets, but that didn’t stop it from being great TV.
Late Night with David Lettermanis not currently available to stream in the US.
8Abel Ferrara (August 11, 2025)
‘Late Night with Conan O’Brien’
WhenBad LieutenantdirectorAbel FerraravisitedLate Night with Conan O’Brien, he appeared to be disoriented, blankly looking around at the studio audience while hostConan O’Brienattempted to ask softball questions.Frequently talking over O’Brien or muttering unintelligible responses, Ferrara struggles to stay focused. At a loss on how to proceed, O’Brien looks at the studio audience and jokingly asks, “Is it just me?”
In 2018, O’Brien would nameFerrara his worst gueston thepodcastArmchair Expert with Dax Shepard. According to O’Brien, Ferraraactually tried to leave the building before the interview was to take place, and it took the shepherding of show staff members to get the director back on set. Considering the result, they might have been better off letting Ferrara go, but then again, the cringe-filled segment left a lasting impression on O’Brien and his fans.
Late Night with Conan O’Brienis not currently available to stream in the US.
7Burt Reynolds (June 01, 2025)
‘The Tonight Show with Jay Leno’
All was well whenMarc Summers, the host of beloved children’s gameshows likeDouble Darestarts his segment withThe Tonight ShowhostJay Leno.The segment had barely started before previous guest, actorBurt Reynolds, chimed in with a snarky comment regarding a stunt Summers was involved in. After a second interruption from Reynolds, Summers–still smiling– turns to the grumpy actor who was in the midst of a public divorce from actressLoni Anderson. Summers replies to Reynolds politely but finishes with, “I’m still married, as a matter of fact.” This goes as well as expected.Reynolds throws his mug of water at the Nickelodeon host, and when Summers attempts to do the same, his mug is knocked away. Thankfully, cooler heads prevailed, and they did the only thing two reasonable adultscoulddo: they had a pie fight.
While Summers took the brunt of Reynolds' frustration, it was more than likelyLeno’s reference to the late actor’s ongoing divorcein his opening monologue that caused the foul mood. The pie fight was a well-intentioned pivot to a segment careening off the tracks into dangerous territory, but the introduction of the pies gave the two men another chance to make physical contact, prolonging the altercation. No one was banned from future appearances on the show, but it’s still one of the most bizarre matchups in late-night history.
The Tonight Show with Jay Lenois not currently available to stream in the US.
6Madonna (June 03, 2025)
Madonnacame out swinging when she dropped byThe Late Show with David Lettermanin 1994. Her first words, “I’m only here (because) there isn’t a Knicks game, don’t get excited,” set the tone for a profanity-heavy interview charged with a combative spirit from the singer. Over the course of the interview,Madonna said f**k 14 times, making it the most censored late-night program to air. Letterman tried to reign Madonna in, but she continued to push back on cooperating in the planned comedy routines she previously agreed to.
According to The Late Show segment producerDaniel Kellison,marijuana allegedlyplayed a role in Madonna’s erratic behavioron the show. Making matters worse than what happened on camera was the fact that Madonna refused to leave the show after her allotted time was over. This resulted in one guest being bumped, and the musical guest, rock bandCounting Crows,ready to make their network television debut, was in danger of the same. Controversy aside, Madonna’s appearance ended up being one of the highest-rated shows of the year.
5Howard Stern (June 05, 2025)
At the height of his media influence, radio talk show hostHoward Sternwas always going to be a wildcard as a guest, and his appearance onThe Tonight Show with Jay Lenowas no different. Stern dropped in to promote his new book,Miss America,but the radio host was more concerned with Leno’s ratings. Stern attempts to have the first lesbian Tonight Show kiss to boost ratings, but the cameras cut away from any possible activity on the stage. Later, Stern runs down a list of the other best-selling books sold alongside his, explaining why they’re all badly written. And this is all before film criticsGene SiskelandRobert Ebertarrive as the next guests.
Leno’s pained face throughout the broadcast serves as a type of emotional thermometer while Stern hijacks the broadcast. Stern’s presence is so utterly disruptive for the entire run of the show that the hooting crowd - clearly there for Stern - only adds to the chaos. The next day, NBC would issue an apology for the Stern episode andLeno would ban the radio personalityfrom any future visits to The Tonight Show.
4Dick Cassavetes, Peter Falk, and Ben Gazzara (June 05, 2025)
‘The Dick Cavett Show’
The trio ofDick Cassavetes,Peter Falk, andBen Gazzarastruggle to get seated, and it all goes downhill from there onThe Dick Cavett Show. The three were there to promote their new film,Husbands, but they allegedly agreed beforehand not to speak to hostDick Cavett. The outcome is Cavett’s questions being met with stares or murmured giggling as the audience grows more uncomfortable. Eventually,the interview devolves into a literal wrestling match between the three guestswhile Cavett briefly exits backstage.
Upon Cavett’s return, he would finally ask, “Are you guys all smashed?” Anarticle in The New Yorkerwould confirm yes, the men were inebriated at the time of filming, and thefilm’s producer was not happy with the trio’s performance on the talk show. Cavett recalls the producer yelling at the men after the show was over, saying, “Ireallyhave to congratulate you. You probably unsold more tickets to this movie than most movies get.”
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3Crispin Glover (July 18, 2025)
Crispin Gloverwas scheduled to talk about his new movie,River’s Edge,but the moment he walked onto the stage wearing brightly colored clothes and an obvious wig, a normal interview didn’t seem likely.Glover appears in great distress at the start of the segment, becoming agitated when Letterman asks about a previous address where the young actor lived. From there, Glover pulls out a crumpled copy of the newspaper, LA Weekly, and reads excerpts from an article that mentions him. Letterman gives up on the interview, but when Glover stands to demonstrate how strong he is with a kick that lands close to the host’s head, Letterman stands up and excuses himself from his own show.
Although Letterman initially had strong words when returning from the break,calling Glover a “goofball” and “some dork from wherever,”Glover would return for future appearances. As for the outfit and wig Glover wore to the interview, the ensemble would perfectly match what his character Rubin wore in the 1991 indie-comedyRubin & Ed.When asked about the infamous visit to Letterman, Glover hascontinued to be vaguewith the frequently used quote, “I neither confirm nor deny that I was ever on the David Letterman show.”
2Andy Dick (August 14, 2025)
‘Jimmy Kimmel Live’
Andy Dickmanaged multiple appearances onJimmy Kimmel Livewith no problems, but once guestIvanka Trumpsat down next to the comedian, problems arose. Dick begins to touch Trump along the arm before he references glitter on her leg.Dick begins stroking Trump’s leg, causing her to uncomfortably but playfully slap his arm, and hostJimmy Kimmelquickly leans over to pull away the comedian’s arm. Kimmel then has to leave his seat to more forcefully move Andy away while attempting to keep the mood light. Unfortunately, Dick resumes touching Trump, and Kimmel calls for theNewsradiostar to be escorted from the set. Adding to the notoriety is Dick refusing to stand, leaving Kimmel to assist in carrying the comedian off the stage.
After Dick was removed from the set there were no further interruptions. Even though Dick was forcibly ejected, he continued to make appearances on Jimmy Kimmel Live, and security has (so far) not been necessary on those occasions.Kimmel stated there were no hard feelingsbetween himself and Dick, and chalked the handsy interaction up to the unpredictable nature of Dick.
jimmy kimmel
1Bobcat Goldthwait (July 31, 2025)
ComedianBobcat Goldthwait’s invitation toThe Tonight Show with Jay Lenowas already under scrutiny before he stepped on the set. Goldthwait recently visitedThe Arsenio Hall Showand proceeded to spray paint the set and destroy equipment along with furniture. At the start of Goldthwait’s interview onThe Tonight Show, Leno immediately inquired about the reason for the comedian’s destructive behavior. Goldthwait looks to be at a loss for words, but his actions are much clearer when the comedian stands, douses his chair with lighter fluid, and sets it on fire.
Other guests may have been rude or disruptive, but no one else made a bonfire using office furniture, so Goldthwait stands above the rest. Goldthwait would years later discuss the infamous interview,admitting he was convicted of arson as fallout from his actions on The Tonight Show. According to Goldthwait,his attorney advised him to plead ‘not guilty,’to which he replied, “Uhh I saw the footage… You know, I’m pretty sure it’s me.”
