David Letterman’s contribution to comedy is inarguable. Before he signs off late night for good, relive some of his best (and worst) moments.
You don’t get to the top without hitting a few bumps in the road– and no one knows that more than David Letterman. The living legend, 68, signs off from The Late Show for good on May 20, after an illustrious 33 years in the late night game. To bid Dave adieu, we’ve compiled the ten most memorable moments from his vast late night career because, when you’ve had everyone from Madonna to President Barack Obama on your show, it can’t always go smoothly right?
David Letterman’s Worst Moments:
5. Lindsay Lohan‘s Pre-Rehab Interrogation: Back in 2013, LindsLo was preparing once again to head to rehab, following embarrassingly public incidents of theft. Of course, Dave wasn’t going to have the Mean Girls actress on without addressing her indiscretions directly. “I have routinely made jokes about you and activities– true and otherwise,” Dave said. He then took to the archives, reading several of said jokes (which were cringe-worthy, to say the least), before asking her some honest questions. “Aren’t you supposed to be in rehab right now? How many times have you been to rehab? Why will this time be different?” Dave pressed. “We didn’t discuss this in the preinterview,” Lindsay said with a chuckle.
4. Michael Richards Apology: In 2006, beloved Seinfeld star Michael Richards, who originated the iconic role of Kramer, committed a major misstep when he repeatedly used the N word during a standup routine. Days later, Michael’s pal Jerry Seinfeld paid Dave a visit, and he introduced Michael live via satellite to apologize on air. It was uncomfortable and bizarre and, frankly, may not have been all that helpful.
3. Sacha Baron Cohen as Borat: Fans of the British comedian are used to squirming during his material, but his in-character interview in 2007 was intense, even for those who were accustomed to his comedy. “My hobbies are ping pong, disco dance and also I like to take photographs of ladies while they make toilet,” he said to guilt-ridden laughter.
2. Joaquin Phoenix Bizarreness: “You look different than I remember you,” Dave told Joaquin in 2009, speaking for, well, everyone. The interview was so bizarre it caused many to wonder whether he was filming some kind of mock-documentary. It turned out later that it was a spoof but, to this day, no one is entirely sure what the deal was beyond its annoyance– and that beard is still nightmare inducing.
1. Extortion Monologue: In what was by far Dave’s most uncomfortable moment throughout his show, he decided to come clean about an issue back in 2009. During a 10-minute monologue, he calmly explained that, “I have had sex with women who work on this show,” and that he was being extorted for $2 million by someone who was threatening to blackmail him. Much to Dave’s credit, he decided ultimately to reveal the truth on his terms, and managed to make his audience laugh the whole way through. Still, we can’t imagine it was his best day.
David Letterman’s Best Moments:
5. Madonna Calls Dave Out: “Why are you so obsessed with my sex life?” Madonna asked Dave seconds after sitting down for this iconic interview in 1994. “Go kiss a guy in the audience,” Dave tells her, which Madge does not appreciate. “Incidentally, you are a sick f–k,” Madonna tells him, to whooping cheers from the audience.
4. Paris Hilton, Fresh Out Of Jail: The year was 2007, and the most important thing to have ever happened was that America’s collective heiress Paris Hilton had done hard time in jail. The interview starts off casually enough, with Dave asking if Paris preferred New York or LA. And then, just as casually, Dave asks, “How’d you like being in jail?” “Not too much,” the bubbly blonde replied. Go figure.
3. Drew Barrymore Flashes Her Boobs: 20 years ago, when Drew Barrymore herself was just 20, she stopped by The Late Show, and decided to bare her soul for Dave– as well as what was under her sweater. The rambunctious gal climbed onto Dave’s desk while executing some hip-swaying moves before lifting up her shirt and showing the talk show host her breasts. Then of course, she knelt down and gave him a peck on the cheek. We have to think this episode might top Dave’s own list of favorite moments as well.
2. Johnny Carson Tribute: Following the death of Dave’s idol Johnny in 2005, he opened the show surprisingly without a mention of his passing, nor any other current event. Only when he sat down did he explain that the monologue had actually been written by Johnny for Dave’s first show. It was a perfect way to commemorate his fallen hero.
1. Dave’s Post 9/11 Monologue: If you need proof that Dave is a comedic hero, this is it. Following the brutal attacks in New York City in 2001, the country was left devastated, looking at a world no one understood. It was people like Dave who restored normalcy and provided comfort to a terrified nation. Dave returned to the air– from the heart of NYC– one week after the events, and he said, “I just need to hear myself talk for a few minutes so that’s what I’m gonna do here.” It’s what we all needed. Though he wasn’t sure whether he should do the show, he explained why he ultimately decided to go for it. “The reason I am doing a show and the reason I am back to work is because of Mayor Giuliani…Mayor Giuliani implored us to go back to our lives and to continue to try to make New York City the place that it should be.”
It will be hard to imagine a New York without Letterman, but how lucky we are to have had him at all.
What’s your favorite Letterman moment?
— Casey Mink