Top 10 David Letterman TV Moments

The United States, and especially New York City, was in no mood for comedy following the terrorist attacks on September 11th, 2001. Letterman was the first late night comedian to return to the air, and gave an emotional monologue to open his first show back. Letterman was visibly distraught but gave a heartfelt speech that praised then-Mayor Rudy Giuliani, the police and fire departments. He ended by calling New York City the greatest city in the world, which would become the tagline of the show.

Letterman can be pretty tough on his guests, and even made Lindsay Lohan cry at one point. Although Paris Hilton didn’t cry, she was visibly angered by Dave’s constant questions about her time in jail. Paris allegedly believed she had been invited on the show to talk about her perfume and new film, but instead was grilled by Letterman about what jail was like, including what the meals were and if they had locked up her friend Nicole Richie as well.

While Letterman was never afraid to make fun of himself and his life on air, he kept the details of his personal life relatively private. That all changed in October of 2009, when he confessed, on air, to having had sexual affairs with female members of his staff. Perhaps more shockingly, he gave details of an extortion attempt against him from a man who was seeking $2 million or he would tell the public all the details of Dave’s sexual escapades.

Farrah Fawcett is not the first celebrity to try to hang on to success, but she may have spent too much time in the tanning bed before this interview. Fawcett told long, nonsensical stories that left everyone, including Letterman, incredibly confused. The interview sparked rumors that Fawcett was on drugs or drunk, although it was later suggested that she was attempting to play the ditzy blonde to promote Playboy magazine. We’ll let you decide.

Letterman isn’t afraid to antagonize his guests, and this interview with Madonna may be the perfect example. Dave set the stage by introducing her as “having slept with some of the biggest names in the industry”, and Madonna retaliated by saying she was only there because there wasn’t a Knicks game on. She then proceeded to drop the F-bomb 14 times, claim that she gave Dave a pair of her underwear, and made countless sexual innuendos, including a joke about NBA players and the microphone.

Jay Leno may have landed “The Tonight Show” gig, but it was Dave who got the last laugh when he secured Johnny Carson’s final TV appearance in 1994. Carson, who first appeared on Letterman in 1985, walked on stage to thunderous applause from the audience. Letterman gave him the host chair, and for a second it seemed like Carson would reclaim his throne. He then shook his head and, as all legends do, walked off into the sunset.

With Andy Kaufman, it was nearly impossible to tell if something was real or staged. Kaufman appeared on Letterman with wrestler Jerry Lawler, who had injured Kaufman’s neck in a wrestling match. Kaufman demanded an apology from Lawler because of the injury, while Lawler mocked Kaufman’s neck brace. Lawler eventually had enough, and slapped Kaufman so hard that he fell out of his chair. Kaufman unleashed a verbal tirade on Lawler and threw a cup of coffee at him. Staged or not, this is definitely one of the more memorable moments in television history.

Okay, okay, so this was a stunt performed by Joaquin Phoenix and Casey Affleck for the film “I’m Still Here”…regardless, this was one of the strangest moments in the history of Letterman’s career, and it showed just how funny but ruthless the late night host could be once he got his hands into you. To be fair, Phoenix was asking for it with his untamed hair, lumberjack beard, and dark sunglasses.Letterman hammered Phoenix, asking him about his time with the Unabomber and mocking his music career. He ended the interview with the perfect line: “And, uh, Joaquin, I’m sorry you couldn’t be here tonight”.

Phoenix may have been taking a page out of Crispin Glover’s book, who appeared on Dave’s “LateNight” show in 1987 and nearly ended up kicking Letterman in the face. This interview was bizarre and uncomfortable, as Glover read random clips about himself from the newspaper. Perhaps more miraculous was that Letterman allowed Glover to ramble on incoherently, until Glover almost kicked him in the face, at which point Dave walked off the set.

Before we unveil our number one pick, here are a few honorable mentions:
- Michael Richards Apologizes Via Satellite
- First ‘Late Show’ After Heart Surgery
- Dave Goes After Bill O’Reilly
- Bill Murray as the First Guest
- Warren Zevon’s Last Appearance

Wait, are we sure this was the cute, innocent little girl from “E.T.”? This interview started off perfectly normal, but things heated up when Dave mentions Drew’s recent appearance at a club where she stripped. Everyone, including Dave, was stunned at what happens next, as Barrymore jumped onto the desk and lifted her shirt up, giving Letterman a full view. Courtney Love would attempt to replicate this act in a future interview, but it didn’t come close to reaching the same heights as Barrymore’s act, which Letterman still talks about to this day.

Do you agree with our list? What is your favorite David Letterman moment? For more great Top 10s published daily, be sure to subscribe to WatchMojo.com.