Updated: Apr 8, 2014 1:12 pm
The talk-show host has had his fair share of crazy interviews! We highlight his weirdest...and BEST...ones!
Paris Hilton - 2007
The heiress appeared on the show right after her jail stint, and Letterman made it clear that was ALL he wanted to talk about. After being asked numerous questions about her life behind bars, Paris declared, "I'm not answering any more questions about it. I’m here for my clothing line, my movie and my perfume." After a short pause, Letterman came back with, "How did you like jail?"
Joaquin Phoenix - 2009
The actor debuted a new look on Letterman, appearing on air with a thick beard, messy hair and participating in a truly bizarre interview. At one point, he drank the host's coffee and stuck his used gum onto the Late Show desk. This was supposedly all a publicity stunt for the film, "I'm Still Here," but five years later, we still don't get it.