Celebrities often shine on screen, but it’s their unexpected and awkward moments that truly captivate audiences, like Drew Barrymore’s wild 1995 Late Show appearance where she danced on David Letterman’s desk and flashed him, or Madonna’s infamous 1994 Letterman interview filled with profanity and bizarre antics that left even CBS scrambling.
Sophie Turner gave Conan O’Brien a real slap during a tequila game in 2019, while Sofia Vergara playfully smacked Jimmy Kimmel in 2014 after a crude joke. Jennifer Aniston’s 1998 interview with Letterman turned unsettling when he bizarrely sucked her hair, and Dakota Johnson’s 2018 Ellen appearance featured a sarcastic clapback about pregnancy rumors and awkward clothing jokes. Aubrey Plaza added her own brand of awkward humor on Conan in 2016 by adjusting her boldly designed dress in a chest-mimicking way, catching Conan off guard.
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