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.


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