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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

by Tim Appelo, AARP, October 20, 2017

  • David Letterman
    Dimitrios Kambouris/Getty Images

    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
    John Paul Filo/CBS/Getty Images

    He Goes Off-Script After 9/11

    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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  • Bill Murray's final appearance on the Late Show with David Letterman in 2015
    Jeffrey R. Staab/CBS/Getty Images

    Bill Murray Threatens Letterman's Life

    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.

    3 of 11
  • Dorothy Mengering on the Late Show with David Letterman in 1997
    CBS/Photofest

    America Falls in Love With His Mom

    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.

    4 of 11
  • Drew Barrymore on the Late Show with David Letterman in 1995
    CBS Photo Archive/Getty Images

    Drew Barrymore Shows Him Her Talents

    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.

    5 of 11
  • Justin Beiber on the Late Show with David Letterman in 2012
    John Paul Filo/CBS/Getty Images

    Justin Bieber Fails Letterman's Exam

    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.

    6 of 11
  • Rupert Jee of 'Hello Deli' next door to 'Late Show with David Letterman'
    Bobby Bank/Getty Images

    Deli Guy Becomes Letterman Sidekick

    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.

    7 of 11
  • Dea Devlin jumps on a pogo stick and plays violin during Stupid Human Tricks on the Late Show with David Letterman
    Jeffrey Neira/CBS/Getty Images

    Humans Outdo Stupid Pet Tricks

    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.

    8 of 11
  • Joaquin Phoenix on the Late Show with David Letterman in 2009
    John Paul Filo/CBS/Getty Images

    He Razzes Oblivious Joaquin Phoenix

    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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  • Farrah Fawcett leaves the Late Show with David Letterman in 1997
    Splash News/Alamy

    Farrah Fawcett Goes Nuts

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

    Teri Garr Cleans Up

    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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