Some of David Letterman’s best moments through the years, from the serious to the very strange


David Letterman announced his plans to retire on Thursday, which got many people reminiscing about his best moments as a host. Of course, after three decades in late-night TV, it’s absolutely impossible to choose which Letterman scene is the most memorable, or to even narrow the list down to a manageable number.

But since he started on “Late Night With David Letterman” at NBC in 1982, there are quite a few moments that will live in TV history, from the ultra-serious to the very funny to the really, really weird. Here’s a rundown of just a few of the more famous ones:

1982: Andy Kaufman and Jerry Lawler get into a bizarre fight.

1987: Crispin Glover acts so strange that Letterman walks off stage.

1994: Madonna makes an expletive-filled appearance.

1995: Drew Barrymore famously flashes Letterman.

1997: Farrah Fawcett freaks everyone out.

2000: Letterman jokes about his quintuple bypass heart surgery in his first show back after the procedure.

2001: Letterman speaks for New York — and America — in the wake of the Sept. 11 attacks with an emotional monologue on his first show back on air.

911 David lettermans reflection on by Yakwild

2005: Oprah and Dave bury the hatchet after years of feuding; neither can remember how the whole thing started.

2007: Letterman grills Paris Hilton after she gets out of jail; Paris isn’t pleased.

2009: Letterman shares details of his affair with a staff member and an extortion plot — it sounds too crazy to be true, except that it is 100 percent real.

2009: Joaquin Phoenix in character? Just being weird? In either case, it was hard to turn away.


David Letterman announces he will retire in 2015

David Letterman: 2012 Kennedy Center Honors profile

GALLERY: David Letterman’s late shows

Emily Yahr covers pop culture and entertainment for the Post. Follow her on Twitter @EmilyYahr.



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Emily Yahr · April 3, 2014