John Paul Filo/CBS
David Letterman Interviews Joaquin Phoenix Even at the best of times, Joaquin Phoenix is a perplexing figure, and David Letterman certainly did not get him at the best of times. During the ramp-up to the 2010 release of the mockumentary I'm Still Here, Phoenix turned his public life into a performance. Phoenix feigned a mental breakdown, a retirement from acting, and the start of a career in hip hop music as part of the movie's marketing strategy. Despite some outrageous behavior, none of these things seemed entirely outside the realm of possibility, given Hollywood's track record of producing broken individuals.
Phoenix appeared on the Late Show as an unresponsive, haggard mess, and Letterman was left to salvage whatever he could from the uncooperative interviewee. There's some debate as to whether the encounter was scripted, but both parties deny that it was; either way, it's delightfully awkward to sit through.