Lindsay Lohan - 2013
Letterman surprised the troubled star by asking about her addictions and personal problems, which Lindsay noted, "we didn't discuss in the pre-interview." But the host redeemed himself by telling the actress he admired her guts to come on the show even after all his jokes at her expense. The sentiment made Lindsay cry.
The talk-show host has had his fair share of crazy interviews! We highlight his weirdest...and BEST...ones!