Harmony Korine (October 17,1997)
Once Letterman went over to CBS (and his show moved up an hour), he started attracting a greater consistency of A-list movie stars and directors. The one downside is that when he came across a dyed-in-the-wool indie auteur, the host's genial tone didn't mix so well with his guests' studied cool. The clearest example of this tension was Letterman's interactions with screenwriter and director Harmony Korine, which peaked on this 1997 appearance to promote the defiantly peculiar Gummo. At one point, the young filmmaker's fumbling, halting half-answers finally drive Dave to turn to the camera and confide, "You're just sitting there in your house, eating Cheetos. You think this is easy, don't you?" In 2013, Letterman revealed to Spring Breakers star James Franco that the reason Korine was later banned from the show was that Dave caught him riffling through fellow guest Meryl Streep's purse backstage.