Photo Special: Letterman’s Legacy! Favorite Broadway, Celeb and Musical Moments From 21 Years of 'Late Show' | Playbill

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Photos Photo Special: Letterman’s Legacy! Favorite Broadway, Celeb and Musical Moments From 21 Years of "Late Show"

By Matthew Blank

May 07, 2015

After more than two decades as host of "The Late Show," David Letterman will retire this month with his final episode scheduled for May 20. We look back at some favorite guests and hilarious moments from the show.

Photo Special: Letterman’s Legacy! Favorite Broadway, Celeb and Musical Moments From 21 Years of "Late Show"

Photo Special: Letterman’s Legacy! Favorite Broadway, Celeb and Musical Moments From 21 Years of "Late Show"

After more than two decades as host of "The Late Show," David Letterman will retire this month with his final episode scheduled for May 20. We look back at some favorite guests and hilarious moments from the show.
41 PHOTOS

Bill Murray spray paints Dave's desk on the first taping of the show, August 30, 1993 — Bill Murray spray paints Dave's desk on the first taping of the show, August 30, 1993 CBS

Paul Newman surprises Dave from the audience at the first taping, August 30, 1993 — Paul Newman surprises Dave from the audience at the first taping, August 30, 1993 CBS

Robin Williams on the second taping, August 31, 1993 — Robin Williams on the second taping, August 31, 1993 CBS

Vice President Al Gore cracks an ashtray with a hammer, September 8, 1993 — Vice President Al Gore cracks an ashtray with a hammer, September 8, 1993 CBS

Sean Connery enters the stage via Jet Pack, October 25, 1993 — Sean Connery enters the stage via Jet Pack, October 25, 1993 CBS

Ray Charles performs, May 9, 1994 — Ray Charles performs, May 9, 1994 CBS

Chris Rock, June 13, 1994 — Chris Rock, June 13, 1994 CBS

Drew Barrymore turns to the audience after flashing Dave, April 12, 1995 — Drew Barrymore turns to the audience after flashing Dave, April 12, 1995 CBS

David Bowie, September 25, 1995 — David Bowie, September 25, 1995 CBS

Jerry Seinfeld and David Duchovny, November 10, 1995 — Jerry Seinfeld and David Duchovny, November 10, 1995 CBS

In his 21 years with "The Late Show With David Letterman" on CBS, the talkshow host has welcomed numerous guests from Broadway, including Glenn Close (costumed as Norma Desmond) during her run in Sunset Boulevard, as well as the casts of Once, Godspell, Nice Work If You Can Get It, Spider-Man and The Book of Mormon, along with Sutton Foster and the cast of Anything Goes, and Norbert Leo Butz and the cast of Catch Me If You Can.

Each December Letterman welcomes Hairspray star Darlene Love to perform the holiday rock tune "Christmas Baby Please Come Home."

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