Late night television has seen its share of unforgettable moments with guests who stole the spotlight. From David Letterman’s chilling blackmail confession to Andy Dick’s inappropriate behavior, the lineup has been anything but dull. Madonna’s fiery exchange with Letterman, Nicole Kidman’s surprising revelation about Jimmy Fallon, and Drew Barrymore’s impromptu birthday dance added to the drama. However, it wasn’t all fun and games; Michael Richards had to apologize for a racially offensive rant, while Marlon Brando’s playful antics with Larry King made headlines.

Paris Hilton’s uncomfortable interview with Letterman, Harrison Ford’s Star Wars standoff with Jimmy Kimmel, and Barack Obama’s humorous take on mean tweets brought laughter. Matt Damon’s revenge prank on Jimmy Kimmel, Heidi Klum’s wardrobe malfunction, and Richard Simmons’s fiery food steamer mishap rounded out the list of unforgettable late-night moments. Whether it was drama, humor, or unexpected surprises, these guests made late-night television impossible to ignore.