Top 20 Most Awkward Moments on Late Night
#20: Letterman Grills Janet Jackson About the Super Bowl
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“Late Show with David Letterman” (1993-2015) Janet Jackson’s career was put in major jeopardy on February 1, 2004. During the Super Bowl halftime show, she was accidentally “dressed down” by her co-performer, Justin Timberlake. Jackson unfairly received the majority of the blame for the incident and was blacklisted in many places. Just under two months later, she made a rather awkward appearance on “Letterman.” Although Jackson clearly doesn’t want to answer any questions about the incident, he keeps pushing for answers and making jokes. She increasingly gets more dejected as Letterman keeps going. While he tries to shift blame to Timberlake, Jackson makes it clear many times that she’d much rather move on from this uncomfortable interview.
#19: When Michael Richards Apologized with Jerry Seinfeld
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“Late Show with David Letterman” (1993-2015) Michael Richards is another celebrity who faced a career-ending controversy - only this one was his fault. The comedian was filmed making a racist tirade against hecklers at the Hollywood Laugh Factory in 2006. Richards tried salvaging his reputation by appearing on “Letterman” via video next to his old co-star Jerry Seinfeld, present for moral support. Unfortunately, it only made things much worse. The audience giggles throughout the whole thing through either awkwardness or a pure misunderstanding if his appearance was a bit or not. Ironically the interview felt like a “Seinfeld” scene in real life. This failed salvage attempt was later parodied by numerous shows and people ― even Richards himself.
#18: Bobcat Goldthwait Set a Chair on Fire
“The Tonight Show with Jay Leno” (1992-2009; 2010-14) Some people just like causing trouble and watching the world burn. Goldthwait just might be one of them. Only in this case, he started with a chair. During his appearance on “Jay Leno,” Goldthwait stood up and randomly set the furniture on fire. Leno professionally runs with the bit. However, the audience clearly doesn't know how to react. The fire-setting is met with some uncomfortable laughter and immediate attempts to douse the flames. After Leno awkwardly forces Goldthwait back into the doused chair, the comedian slips on his way off the stage. You know, just to add to the cringe of it all. The comedian was forced to pay over $3,000 in fines and reimbursements for making everyone feel awkward.
#17: When Jimmy Fallon & Dakota Johnson Knocked On Each Other’s Teeth
“The Tonight Show Starring Jimmy Fallon” (2014-) There are a few things we never thought we’d see on late night TV, and people tapping on each other’s teeth is certainly one of them. Jimmy Fallon brings up the fact that a gap in Dakota Johnson’s teeth had closed. That led to an extended discussion about their respective dental work. This bizarre detour gets stranger when Johnson is asked to feel the host’s fake tooth before proceeding to tap on it with her nail. Even Fallon looks confused about the whole thing, but he later responds and taps on Johnson’s teeth as well. Their chemistry is admittedly great. However, there’s a degree of weirdness about the whole thing that makes for a rather uncomfortable watch.
#16: When David Letterman and Shirley MacLaine Clashed
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“Late Night with David Letterman” (1982-93) For certain celebrities, heading onto “Late Night” in the ‘80s was akin to throwing raw meat into a hungry lion’s cage. Dave mellowed out in his later years, but early on he could be quite confrontational – or as Shirley MacLaine calls him: an asshole. Part way through this interview, Dave wanted to talk about Shirley’s belief in reincarnation, but the actress didn’t think there was time to do so. And, as Dave kept pushing the topic, MacLaine let Dave know what she thinks of him. What’s truly remarkable about this scene is that neither guest nor host attempted to make up or play nice for TV, and the barbs just kept coming until the interview (mercifully) ran out of time.
#15: When Andy Dick Was Escorted Away by Security
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“Jimmy Kimmel Live!” (2003-) Andy Dick has seen his fair share of controversies throughout the years, and he’s no stranger to being hauled away by authority figures. Back in 2007, Dick appeared on “Jimmy Kimmel Live!” alongside Ivanka Trump and seemingly took a liking to her. He repeatedly strokes her bare leg. Initially, Kimmel and Trump try to downplay his creepy behavior. But after he continues to touch her inappropriately, he’s quite literally dragged off stage by security. A ton of music and smiles try to hide how uneasy the whole affair was. But things only feel okay once Dick was completely removed from the stage.
#14: When Guy Ritchie Had Open Contempt for David Spade
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“Jimmy Kimmel Live!” (2003-) Since late night shows depend heavily on talking with guests, it can be incredibly painful when someone is just not in the mood. David Spade learned that the hard way when he was filling in for Jimmy Kimmel and tasked with interviewing famous director Guy Ritchie. We use the word “interviewing” very lightly here, as there wasn't much of that going on. It begins well enough with some friendly banter. But when Ritchie shuts down, Spade has to carry the segment solo With what must have been a really sore back, Spade later emailed Kimmel and asked if this was a prank.
#13: When Bill Burr and Sarah Silverman Had It Out
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“I Love You, America with Sarah Silverman” (2017–18) This conversation between Burr and Silverman was so cringe and confusing that we’re still not sure what happened almost two years later – and neither is the Internet! Either these two are very close and are just taking the piss out of each other, or this was an impromptu therapy session exploring their likes and dislikes for each other. And, honestly, not knowing for sure makes it all the more uncomfortable! To be fair to Sarah though, Burr is usually on the defensive when it comes to interviews, and doesn’t exude much in terms of emotion (unless you count sarcasm and paranoia!); so, all things considered, it could have gone much worse… right?
#12: When Bill O'Reilly & David Letterman Talked Politics
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“Late Show with David Letterman” (1993-2015) They say you should never talk about religion or politics. The topics are too complex, people are defensively passionate about them, and one wrong word can lead to a fierce argument. It’s a piece of advice that David Letterman and Bill O'Reilly should have taken. O'Reilly was one of the most prolific political commentators of the time. During his shows, he was known for sticking hard to his opinions. His determination met Letterman on late night. The comic host gets in a hostile argument with his guest. As a result, imbues the segment with a really dark and uneasy tone. Watching people vehemently argue about politics and war doesn’t really make for entertaining late night TV.
#11: When Donald Trump Appeared on Colbert
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“The Late Show with Stephen Colbert” (2015-) Since Colbert and Trump are opposite ends of the political spectrum, putting them in a room together was always going to be a risk. Sometimes oil and water just don’t mix, and there’s no forcing them to mix. Trump appeared on “Colbert” in September 2015 shortly before being elected president. There’s a jokey and faux-friendly tone to the conversation. However, there’s also thinly veiled contempt between the two. There’s also a rough patch where Colbert’s attempt to joke about Trump’s immigration policies gets suddenly serious. In the end, it feels like the politician is just making a campaign stop instead of a late night appearance. Despite Colbert’s best attempts to keep things light and fun, the interview comes out as awkward.
#10: When Kanye West Compared Himself to Jesus
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“Jimmy Kimmel Live!” (2003-) To say Kanye West has said his fair share of controversial things throughout the years would be an understatement. When he appeared on “Jimmy Kimmel Live!” back in 2013, he made some truly bizarre comments. During a monologue, West called himself a creative genius and compared his output to the likes of Leonardo Da Vinci and Jesus. West also goes on several long tangents that often have nothing to do with the questions that are actually being asked. While Kimmel largely keeps everything on the rails, the whole conversation still feels off. (xref) This wouldn’t be the last time that West gave an awkward interview on the show. The musician later discussed his affiliation with Donald Trump and his extremist views.
#9: When Norman Mailer Went After Gore Vidal
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“The Dick Cavett Show” (1969-75) It’s hard to imagine any interview in this day and age starting out with a headbutt backstage; but, that’s just what happened here. Cavett’s infamous interview featured two literary heavyweights, squaring off over their intense dislike of one another. Mailer was a critic of the feminist movement, and Vidal took his views to task in an essay where he likened Mailer’s misogyny to that of serial killer Charles Manson. Mailer, who had been drinking, was furious with Vidal’s article and subsequently couldn’t maintain his composure in person, headbutting and cursing Vidal backstage while openly insulting everyone (including the host and female guest) on stage. Talk about intense.
#8: When Abel Ferrara Went Off the Rails
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“Late Night with Conan O’Brien” (1993-2009) If you’ve seen Ferrara’s 1992 film “Bad Lieutenant,” you’d know that the director is not afraid of controversy – which Conan acknowledged while inviting him onstage at his old show. So, not surprisingly, controversy is exactly what ensued… Ferrara was accused of showing up drunk, refusing to go on stage, and – at one point – even leaving the NBC studio, requiring staff members to track him down. And, if you thought that sounds like a mess, just watch the interview. Ferrara is barely audible at times – slurring and rambling incoherently – to the point where Conan suggests viewers will need subtitles to understand him. Conan later admitted that, in his entire career, Abel Farrara was by far the absolutely worst guest he’s ever interviewed.
#7: When Jimmy Kimmel Mocked Jay Leno to His Face
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“The Jay Leno Show” (2009-10) Remember the Late Night Wars? Well, Jimmy Kimmel sure had a take; and, he didn’t take kindly to Jay Leno’s actions, ruthlessly mocking and impersonating Jay during Leno’s drawn-out “Tonight Show” dustup with Conan O’Brien. For some odd reason, Leno’s producers then thought it a good idea to have Kimmel on Jay’s new show; and, well, it plays out exactly as you’d expect. Leno clearly hates Kimmel’s impression of him, and Jimmy takes every opportunity to insult Jay on his own show. Watching Leno forcing himself to laugh while Jimmy drops bombs on him is the equivalent of having to smile while being punched in the face. Ouch!
#6: When David Letterman Hounded Paris Hilton
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“Late Show with David Letterman” (1993-2015) Unfortunately for celebrities, interviews don’t always go as discussed beforehand, especially when attempts at comedy are made at their expense. In 2007, Paris Hilton was sentenced to 45 days in jail. This was of course publicized, but the star obviously didn’t want to talk about it. She appeared on “Late Show with David Letterman” with the intention of promoting and discussing her new perfume and projects. Letterman, however, had different ideas and began to extensively question her about her time in jail – and her friend Nicole Richie’s. He also had questions about the food there, for some reason. In fact, he’s just unfair at some points, and we kind of wish there was a referee present to stop the fight.
#5: When Andy Kaufman Fought Jerry Lawler
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“Late Night with David Letterman” (1982-93) Many people refer to Kaufman as a comedian, but he labeled himself a “song and dance man,” and he gained fame for his unconventional approach to fame and entertainment. One of his many ventures was professional wrestling. During his career, he entered into a staged feud with Jerry Lawler. The two appeared together on “Late Night with David Letterman”. The tension culminated in the wrestler slapping Kaufman out of his chair. In turn, the comedian screamed obscenities at Lawler. It’s a brilliant piece of performance art, but no one knew that at the time. They thought it was real, and for them, the encounter was horrifically tense.
#4: When Crispin Glover Nearly Kicked Letterman In the Face
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“Late Night with David Letterman” (1982-93) On the night of July 28, 1987, Crispin Glover made an unforgettable late night appearance. He donned a wild wig, jittered around erratically, and spoke nervously. Glover seemed to be incredibly uncomfortable just sitting in place. But things really went south after the actor challenged Letterman to an arm wrestle. After Letterman refused, Glover did a wild kick that was aimed in the host’s direction. Most speculate that his behavior was simply early publicity for the movie “Rubin & Ed,” in which Glover acts in a similar manner. However, the actor has never divulged his real motivation, and it remains tantalizingly elusive.
#3: When Jennifer Garner Got Schooled
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“Late Night with Conan O’Brien” (1993-2009) Conan went to Harvard. And while that doesn’t always mean anything, he is clearly a sharp guy. So, Garner probably shouldn’t have called out O’Brien for his (ultimately correct) language usage before mocking his education at one of the best universities in the world. But, she did. Luckily it was all in good fun, but – being the nerd he is – Conan couldn’t let the opportunity pass to whip out a dictionary and school Garner (quite literally). Jennifer goes from confidently, and enthusiastically, talking about her latest role to utter silence – with more than a hint of embarrassment – as Professor O’Brien rubs it in.
#2: When Madonna Let Loose
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“Late Show with David Letterman” (1993-2015) Just like you never know how a Letterman interview will go, you never know how a Madonna guest appearance will turn out! But, we know one thing for sure: everyone at the FCC was having a collective heart attack during this profanity-ridden, innuendo-driven, filthily funny interview! Oh, where to begin, really?? Countless F-Bombs and anatomy jokes are one thing, but it’s Madonna’s constant insistence that Dave’s obsessed with her sexually, and – while never denying this claim – Dave’s flirty behavior that really makes this one for the ages. Do they like each other? Do they loathe each other? Just what are we watching here? It feels like either a fight or a snog-fest is about to break out and both outcomes are equally as worrisome.
#1: When Joaquin Phoenix Seemed Nutty
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“Late Show with David Letterman” (1993-2015) When looking back, we know Phoenix had a whole shtick that turned out to be a wacky piece of performance art for a mockumentary that he and Casey Affleck were making. But in 2009, the world collectively thought that the actor had fully lost his mind. He claimed he was transitioning to a career in hip-hop, yet he could barely string two sentences together in real time. Was he drunk? High? Sick? Dying? For every time someone asked one of these questions, the outcome was a torrent of opinion pieces and endless speculation that filled the Internet for months. Yet, the one thing we didn’t get –for over a year-and-a-half – was answers. Joaquin returned to “The Late Show” in 2010 and apologized for his behavior, but even that interview was a little awkward!
