10. Drew Barrymore
When Drew Barrymore comes bounding on stage sans bra bearing a gift of flowers for Letterman, there is no indication of what you’re in store for. After a relatively tame conversation about Drew’s recent appearance at a club where she stripped off for a ‘performance piece’, she bravely offers Letterman a sneak peak and jumps up on his desk giving him a full frontal flash. Unlike the Courtney Love incident though, it’s a very hot moment which Letterman thoroughly enjoys, taking down the details of the aforementioned club. Letterman you old dog! Unfortunately the audience don’t get to see Drew’s goods, and it goes back to tame-city after that.