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Letterman's Ultimate Top 10 List

David Letterman wins the Mark Twain Prize — and AARP honors his best 10 moments onscreen

  • David Letterman
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    Great Late Shows With David Letterman

    David Letterman will receive the 20th annual Mark Twain Prize for American Humor at a televised ceremony Oct. 22 at the Kennedy Center in Washington, D.C. The gap-toothed funnyman follows past winners Richard Pryor, Tina Fey, Carol Burnett, Ellen DeGeneres and Bill Murray. In his honor, here are 10 of Letterman's most memorable moments.

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  • David Letterman during the opening of the Late Show with David Letterman on Monday, September 17, 2001
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    He Goes Off-Script After 9/11

    Six days after the 2001 terrorist attacks, Letterman tackles the toughest assignment of his life. The first entertainer to return to air after 9/11, he put his clown mask aside and unified the nation with a heartfelt, painful, healing, uplifting unscripted hour.

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  • Bill Murray's final appearance on the Late Show with David Letterman in 2015
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    Bill Murray Threatens Letterman's Life

    Letterman's first — and last — guest, Bill Murray, vowed to "make his life a living hell" in retaliation for Letterman's "mind games," noting, "I had a chance to strangle Richard Nixon and I didn’t — and I regret it!” But Murray returned to the show 42 times, dressed as Liberace, Peter Pan and a guy jumping out of a giant cake.

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  • Dorothy Mengering on the Late Show with David Letterman in 1997

    America Falls in Love With His Mom

    Unflappable, drier-than-Dave wit Dorothy Mengering interviewed Olympic athletes and Hillary Clinton, but her most delicious bits were her "Guess Mom's Pies" skits, which led to a bestselling cookbook. She outed irascible intellectual Letterman as just another Midwest kid who loved his mother.

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  • Drew Barrymore on the Late Show with David Letterman in 1995
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    Drew Barrymore Shows Him Her Talents

    The scion of America's noblest theatrical family impulsively jumped on Letterman's desk in 1995 and flashed her chest in an extremely personal 48th birthday present for the host, who said, "I can't thank you enough for that."

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  • Justin Beiber on the Late Show with David Letterman in 2012
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    Justin Bieber Fails Letterman's Exam

    America's big singer — not a big reader — got quizzed by Letterman on his knowledge. Bieber revealed that he thought Canada and the North Pole were continents, and called the Sistine Chapel “the Sixteenth Chapel.”

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  • Rupert Jee of 'Hello Deli' next door to 'Late Show with David Letterman'
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    Deli Guy Becomes Letterman Sidekick

    Deadpan (yet obviously amused) Rupert Jee, whose Hello Deli sold sandwiches next door to Letterman's studio, costarred in 200 episodes, including a 1995 bit where Jee impersonated a vendor who threatened to take off his pants if bypassers didn't buy his hot dogs.

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  • Dea Devlin jumps on a pogo stick and plays violin during Stupid Human Tricks on the Late Show with David Letterman
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    Humans Outdo Stupid Pet Tricks

    Though some prefer Stupid Pet Tricks like Hammer the pit bull, who bowled a strike, Letterman struck more comedy gold with humans, including the violinist who performed on a pogo stick. He may have topped her when he donned a suit made of 3,400 Alka-Seltzers and got dunked. What a comic relief it was!

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  • Joaquin Phoenix on the Late Show with David Letterman in 2009
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    He Razzes Oblivious Joaquin Phoenix

    A wizard with difficult guests, Letterman's magic was evident when Phoenix showed up not as himself but in character as a bearded space case in 2009. (Crispin Glover pulled a similar stunt when, playing his River's Edge character without informing Letterman, he karate-kicked the host's head.) "It was so much fun, it was batting practice," the host later told Phoenix — whose oversize beard Letterman recently outdid.

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  • Farrah Fawcett leaves the Late Show with David Letterman in 1997
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    Farrah Fawcett Goes Nuts

    Celebrating her remarkably youthful nude Playboy spread at age 50 in 1997, a dazed Fawcett mistook Letterman's set backdrop photo for a real window on Manhattan, and said things like, "You know Central Park? I’m sorry, of course you do…. Is that sort of near the zoo?" Letterman replied, "There’s a zoo in Central Park — the Central Park Zoo is right there." Catching on, Fawcett said, "You’re making fun of me!"

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  • Teri Garr on the Late Show with David Letterman in 1985

    Teri Garr Cleans Up

    So what if Letterman smooched Julia Roberts five times in her 27 appearances? His long-term crush was on Garr, star of Young Frankenstein and After Hours. She showered on camera for him in a 1985 show, wailing, "I hate you!" Letterman said, "I’d marry this woman in a second if she’d have me.”

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