The 30 Most Outrageous Late-Night TV Moments Ever
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Over the years, late-night hosts have gifted us magical moments that we won’t be forgetting any time soon—some cringeworthy (forced apologies, embarrassing breakdowns), some hilarious (long-running running bits, scathing takedowns), and some just straight-up absurd (anything to do with Andy Kaufman ). For your entertainment, we’ve gathered the 30 best here. So read on, and enjoy. And for more outrageous television spots, be sure to check out the 30 Funniest Reality Show Moments of All Time .
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After the Hall of Presidents and First Ladies Museum, a home to frighteningly realistic wax figures of presidents and first ladies shut down, John Oliver and the producers behind Last Week Tonight purchased not one but five figures—for, according to the Boston Globe , five figures. ($13,700, to be precise.) The purpose? To make this “ movie trailer ” about President Warren G. Harding . For more on the zaniness of elected office, don’t miss The Crazy Times Politicians Totally Lost Their Cool .
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In 2009, David Letterman set aside the bits and got serious. On live television, he admitted to having sexual affairs with coworkers and subsequently revealed a $2 million blackmail scheme; if Letterman didn’t pay up, everyone would learn the truth about his impropriety. But the host got in front of the scandal and cooperated with police, eventually leading to the arrest of a producer Joe Halderman .
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In 2012, President Barack Obama swung by The Tonight Show to “slow jam” the news with Jimmy Fallon . And for more TV fun, don’t miss the 30 Funniest Reality Show Catchphrases of All Time.
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In 2016, the duo did it again !
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Everyone remembers when Kanye West interrupted Taylor Swift at the 2009 Video Music Awards. But what people might not know is that, during an apology on The Tonight Show , the rapper broke down crying—on live television.
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Way before her father kicked off his 2016 presidential campaign, Ivanka Trump appeared on Jimmy Kimmel Live! alongside Andy Dick . Throughout the interview , Dick kept inappropriately touching Trump to the point that he had to be carted off the stage by security—while cameras were still rolling.
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In a routine that is, in hindsight, obviously satirical, Andy Kaufman ‘s legendary panhandling bit wasn’t initially viewed as such, with some folks in the audience actually reaching into their coffers and handing over cash to the Dadaist comic.
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Stephen Colbert and Bill O’Reilly have a long history; but appeared each other’s shows, usually for the purpose of throwing moral potshots. But, upon O’Reilly’s dismissal from Fox News, Colbert was able to get the last word in —and he truly held no punches. And a collection of some truly great burns, here are the 28 Wittiest Put-Downs Ever Uttered.
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During one particularly noteworthy episode of Last Week Tonight with John Oliver , the hostus mostus himself bought up an insane amount of debt—to the tune of $15 million, to be exact—and decided to forgive it all.
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Arnold Schwarzenegger , in true Hollywood-to-Washington fashion, announced his run for governator to rapturous applause on The Tonight Show . He ended up serving two full terms in office, from 2003 to 2011. For more on the celebrity-to-politics pipeline, see how our writer scored on Donald Trump’s infamous cognitive exam .
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In 1995, Hugh Grant found himself in legal hot waters for engaging in sexual activity in a public place. During his first post-arrest interview , with Jay Leno , the refused to treat Grant with kiddie gloves, kicking the questions off with a savage, “What … were you thinking?”
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Glasgow-born Craig Ferguson aired his own attempt at taking a United States citizenship test on The Late Late Show . He passed with flying colors, having answered every question correctly.
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Nicole Kidman revealed to Fallon, in 2015, that, when they first met, she hoped a romance would blossom between them. Of course, this devastated Fallon, who ended up retreating to the on-set couch in exasperation. And for more celeb news, don’t miss the 20 Craziest Celebrity Rumors of All Time.
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In 1995, Drew Barrymore hopped on Letterman’s desk, did a little dance, and flashed him.
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Real Time with Bill Maher host Bill Maher crossed all of the lines by referring to himself using the most forbidden word in the English language.
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After tanking his career by calling an audience member the worst word in the English language during a stand-up routine, in 2006, Michael Richards went on The Late Show with David Letterman to issue an apology . Richards’s subsequent two television roles involved three-episode stints on Curb Your Enthusiasm and Comedians in Cars Getting Coffee , in 2009 and 2014 respectively.
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Jason Sehorn , then a cornerback for the New York Giants, surprised actress Angie Harmon during her The Tonight Show interview with her father in tow—and a “Will you marry me?”
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Yes, This Morning is technically not a late-night show. But trust us: This Video of Ryan Gosling and Harrison Ford Is the Funniest Thing You’ll See All Day .
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These days, you’ll see countless headlines proclaiming that some late night host “destroyed” or “eviscerated” a topic or an interview subject. Most of those claims are hyperbolic. Saying Jon Stewart ‘s interview with Mad Money host Jim Cramer deserves a similar term is not.
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In 2013, eternal grouch Harrison Ford went on The Tonight Show only to end up in an argument with his trusty (fictional) sidekick, Chewbacca.
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During an interview with Conan O’Brien , Jennifer Garner told the host that, “Snuck isn’t a word. You went to Harvard. You should know that.” O’Brien retorted by whipping out a dictionary and proving the actress wrong.
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For Letterman’s 20th anniversary episode, frequent guest Bill Murray showed up on stage as Liberace. (In other appearances, Murray has also popped out of cake, showed up in 1700s garb, and, to celebrate a New York Giants victory, come clad in full football gear.
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Yes, this really happened .
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Throughout the course of an interview with Letterman, to promote the film Two Lovers , Joaquin Phoenix forgets the names of his Two Lovers costars and states that he wants to switch careers and become an actor. As it turned out, this interview was just an instance of Phoenix staying in character and was used as setup footage for the 2010 mockumentary I’m Still Here .
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This may be the first recorded instance of a late show host calling the president of the United States “dude.” It’s “Mr. President,” dude.
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Not literally, of course. But, when NBC decided to give Conan O’Brien his notice, the host fired back by bringing a Bugatti Venyon, the most expensive car at the time, on air and playing The Rolling Stone’s “Satisfaction,” the most expensive song to license at the time, in the background.
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Remember the wax president figures that John Oliver purchased from a defunct museum? Incredulously, five months after his original bit, he brought the figures—including depictions of Richard Nixon and Bill Clinton —back for yet another “ trailer .” Except this time, Oliver increased the star power by adding another all-American figure: Tom Hanks . And for more hilarity, don’t miss the 75 Jokes That Are So Bad They’re Actually Funny .
