Video Evidence: Farrah Fawcett, 1997
Fawcett gave a cringe-worthy interview to David Letterman in 1997. Those who grew up with her famous '70s pin-up poster were likely excited to hear that her interview was going to be sexual in nature. Unfortunately for those horny children of the '70s, the segment played as an exercise in discomfort rather than titillation.
At one point, she described in extremely weird detail just how incredible her gluteus maximus truly is. There are a few moments that go past mere hippie banter and into full-on "cry for help" territory. The few seconds where she stares at the set as though it were an actual skyline (4:06) have to be the low point.