The 30 Most Outrageous Late-Night TV Moments Ever

1 | John Oliver buys a bunch of wax figure presidents.

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.

2 | David Letterman reveals blackmailing scheme.

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.

3 | The Jimmy Kimmel/Matt Damon Feud

The long-running "feud" between Matt Damon and Jimmy Kimmel has, at times, been so harsh that it's tough to see if it's a satirical routine or just real life. This song, cowritten by and costarring Sarah Silverman, is arguably the most brutal bit. But for lighthearted sections of the "feud," read up on why The Video of Them Insulting Each Other That Will Be the Funniest Thing You've Seen All Day.

4 | Barack Obama slow jams the news...

In 2012, President Barack Obamaswung 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.

5 | ...twice.

In 2016, the duo did it again!

6 | Kanye West breaks down.

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.

7 | Andy Dick crosses the line with Ivanka Trump.

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.

8 | Madonna drops 14 F-bombs in one interview.

During one single interview, Madonna dropped 14 F-bombs, setting an at-the-time record for the most-censored late night interview of all time. (In the years since, censorship laws have loosened up, so no one's counting any more.) And to learn more words no one should say—on TV or anywhere—check out: If You're Over the Age of 30 You Won't Know What These Words Mean. 

9 | Andy Kaufman panhandles on Letterman.

In a routine that is, in hindsight, obviously satirical, Andy Kaufman'slegendary 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.

10 | Stephen Colbert bids adieu to Bill O'Reilly.

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. 

11 | John Oliver buys and forgives medical debt.

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.

12 | Arnold Schwarzenegger kicks off run for governor.

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.

13 | Jay Leno grills Hugh Grant.

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?"

14 | Craig Ferguson becomes a citizen.

Glasgow-born Craig Fergusonaired 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.

15 | Nicole Kidman retroactively breaks Jimmy Fallon's heart.

Nicole Kidmanrevealed 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.

16 | Drey Barrymore flashes David Letterman.

In 1995, Drew Barrymorehopped on Letterman's desk, did a little dance, and flashed him.

17 | Bill Maher

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.

18 | Michael Richards attempts an apology.

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.

19 | Jason Sehorn proposes to Angie Harmon.

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?"

20 | John Oliver buys a train.

Having an HBO-backed budget sure makes for some funny bits. During an episode of Last Week Tonight, John Oliver poked fun at a model train on the set of Scranton, Pennsylvania's ABC affiliate. Apparently, some viewers of the affiliate were offended. So, Oliver and his producers dished out for "an irresponsibly large" train set—and donated it to the scrawny news station.

21 | Ryan Gosling and Harrison Ford give a master class in press junkets.

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.

22 | Jon Stewart excoriates Jim Cramer.

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'sinterview with Mad Money host Jim Cramer deserves a similar term is not.

23 | Harrison Ford gets into it with... Chewbacca?

In 2013, eternal grouch Harrison Ford went on The Tonight Show only to end up in an argument with his trusty (fictional) sidekick, Chewbacca.

24 | Conan O'Brien gives Jennifer Garner a grammar lesson.

During an interview with Conan O'Brien, Jennifer Garnertold 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.

25 | Bill Murray dressed up as Liberace.

For Letterman's 20th anniversary episode, frequent guest Bill Murrayshowed 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.

26 | Marlon Brando kisses Larry King

Yes, this really happened.

27 | Joaquin Phoenix bombs an interview.

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.

28 | Jon Stewart calls President Obama "dude."

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.

29 | Conan O'Brien lights $1.5 million dollars on fire.

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.

30 | John Oliver brings the wax presidents back.

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.

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