20 Late Night Show Guests Who Made It Hard To Look Away

…legendary moment in late-night television. Drew Barrymore’s surprise striptease wasn’t just a bold move; it was a defining moment of her transformation from a troubled child star to a confident young actress. The playful and unexpected nature of the performance caught everyone off guard, including David Letterman, who was visibly stunned but delighted by the gesture.

This moment is often remembered as one of the most outrageous and iconic late-night TV moments. It not only cemented Barrymore’s status as a daring and spontaneous entertainer but also contributed to the unpredictable and lively spirit that late-night shows are known for.

These appearances show how late-night TV can become a stage for some of the most unfiltered and unforgettable moments in pop culture. Whether it’s a shocking revelation, an unexpected confession, or a wild stunt, these moments remind us why late-night television has remained a beloved part of entertainment history.