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The Top 10 Most Memorable David Letterman Moments

Drew! Madonna! Joaquin! And more!

Joyce Eng

David Letterman is signing off for good on Wednesday. In his 33 years on Late Night and Late Show, there have been many highs, quite a few lows and plenty of crazy. Here are his top 10 most memorable moments.

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10. Harvey Pekar gets banned (Aug. 31, 1988)
Letterman and Pekar loved ripping on each other. Or just hated each other. It's hard to tell. It all came to a head on Late Night when the crusty American Splendor comic book writer went on a rant about General Electric, NBC's parent company, and accused Letterman of being a "shill" for GE. When Pekar wouldn't shut up, Letterman vowed to ban him for life. (He'd later appear on Late Show.) "I'd rather be liked than thought of as a crazy man, but with Letterman, I've been in a situation where you either lay down and let him insult you or you do something about it," Pekar told The Los Angeles Times in 1995. "Most people keep their mouth shut and let him dump on them. I don't wanna do that."

9. Dave lays into John McCain (Sept. 24, 2008)
The then-presidential hopeful canceled a Late Show appearance at the last minute, claiming that he had to return to D.C. to focus on the economy. Turns out that was a lie: Dave gleefully cut to a live internal feed of McCain prepping for a CBS Evening News interview with Katie Couric. "He doesn't seem to be racing to the airport," Letterman said. McCain would appear on the Oct. 16 show.

8. Warren Zevon's final appearance (Oct. 30, 2002)
Letterman devoted an entire episode to his old pal and frequent guest after he was diagnosed with terminal lung cancer. During the sit-down, the musician openly discussed his illness and imparted some pearls of wisdom. Asked what he's learned about life and death, he mused, "You're reminded to enjoy every sandwich." Zevon then played three songs, "Mutineer," "Genius" and "Roland the Headless Thompson Gunner," which would be his final public performance. He died Sept. 7, 2003.

7. Don't f--- with Madonna (March 31, 1994)
The Queen of Pop, then in her aloof Goth phase, quickly got into some dirty banter after Letterman introduced her as someone who's "slept with some of the biggest names in the entertainment industry." Madge returned the favor by testing Late Show's censor buttons, repeatedly dropping the f-bomb, including calling Dave a "sick f---."

6. Kaufman vs. Lawler (July 29, 1982)
When pro wrestler Jerry "The King" Lawler challenged Andy Kaufman, who had declared himself the "Intergender Heavyweight Champion" after wrestling women as part of his act, Letterman had both men on to settle the score. After some back-and-forth, Lawler slapped Kaufman so hard that he fell out of his chair. When the show returned from commercial break, Kaufman launched into an expletive-filled tirade and threw Letterman's coffee at Lawler. The entire thing may or may not have staged between the two men (depending on who you believe), but the chaotic watercooler moment meant Dave had officially arrived in late night.

5. Johnny Carson tribute (Jan. 31, 2005)
On his first show following Carson's death, Letterman paid homage to the late-night icon, recalling happy memories and moments with his mentor. "The best part about Johnny is when a joke would not go well and he would look at the audience and give them that look like he had just bought them drinks and nobody said, 'Thank you,'" he said. "And then Doc [Severinsen] and the band would start playing ... and then Johnny would start dancing. It was the funniest thing of the night and the funniest thing of the week."

4. Letterman admits to sex scandal (Oct. 1, 2009)
Some of Letterman's most unforgettable moments are when he's candid with the audience, stripping away just enough dry wit and sarcasm to get real. He did so in 2000 when he returned from quintuple bypass heart surgery, but nothing was more human and raw than when Letterman awkwardly navigated through telling viewers about his affairs with female staffers and the extortion plot in which he found himself entangled.

3. Joaquin Phoenix gets weird (Feb. 11, 2009)
Sporting shades and a lumberjack beard, Phoenix dropped by to announce that he was retiring from acting to become a rapper, which was basically the only intelligible things to come out of his mouth during the 10-minute sit-down. (As we later learned, the whole stunt was for Casey Affleck's mockumentary I'm Still Here.) "Joaquin, I'm sorry you couldn't be here tonight. We owe an apology to Farrah Fawcett," Dave quipped at the end, referring to another Letterman Hall of Fame moment.

2. Drew Barrymore's peep show (April 12, 1995)
Upon learning that it was Letterman's birthday, Barrymore, then 20, wished him a happy 48th by dancing on his desk and flashing him. Twelve years later, Barrymore told Letterman hat her wild child days were over, so he shouldn't expect an encore for his 60th. "I'm very grateful for the opportunity. It was lovely," he said. "And it's still something I think about and talk about and tell my friends."

1. Letterman's first post-9/11 show (Sept. 17, 2001)
The first late-night host to return to TV after 9/11, Letterman opened the show with an emotional, honest eight-minute monologue as he tried to make sense of the attacks and explained how and why he chose to return to the air. It's a heartbreakingly cathartic and ultimately hopeful moment for a nation still grieving.

What are your favorite Letterman moments?

Late Show with David Letterman will air its final episode Wednesday at 11:35/10:35c on CBS.

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