#8: Drew Barrymore’s Bold Move on David Letterman’s Show
Drew Barrymore, once the quintessential girl-next-door, turned heads and shattered her wholesome image during a wild appearance on The Late Show with David Letterman. At just 20, she made an unexpected and bold move, dancing on Letterman’s desk before flashing him in a playful, rebellious act.
The live TV moment was as unforgettable as it was awkward, with Letterman laughing through his surprise. Barrymore’s spontaneity added to her growing reputation as a Hollywood wild child, marking a sharp departure from her innocent on-screen persona and leaving a lasting imprint on one of the most memorable talk show moments of the ’90s.