Farrah Fawcett (June 5, 1997)
"You're making fun of me," the former Charlie's Angels star told Letterman during her first appearance on his show. Yes, but what made the segment delicious — and also more than a little sad — was how deadpan Dave was while getting his licks in, and how unaware she seemed to be. On to promote a Playboy cover and a pay-per-view special, Fawcett seems distracted, harried, incoherent — and everybody in the studio knows it but her. The interview is a litany of disasters: Fawcett fumbles through a rambling story about Central Park, a stage manager trips during the broadcast. But the highlight/lowlight has to be the moment when she stops what she's saying to stare at the fake backdrop behind Letterman and exclaim, "Wow…," briefly thinking it's the real New York City skyline. Fawcett, who died of cancer in 2009, claimed in 1999 that her behavior on the Late Show was a "performance." It sure didn't feel that way in the moment.