9 Wildest Late-Night Show Guests

Late-night shows are known for their entertaining and sometimes unpredictably wild guests. Things may start off boring and monotone, but moments later, these celebrities shock the audience with inappropriate revelations and outrageous antics.

Here are some late-night show guests who left a lasting impression, whether through their charm, controversy, or sheer unpredictability.

1. Richard Simmons – Sets Letterman on Fire (1980s-2000s)

No one could outshine Richard Simmons when it came to bringing energy. Whenever you’d see this guy on Letterman’s show, you knew he’d do or say something hilarious or bizarre. One of such standout moments was when Simmons brought a strange kitchen appliance to the set, and it caught on fire. Watching him blast it with a fire extinguisher while Letterman tried to keep it together was one of the funniest moments in TV history.

2. Madonna – Queen of Controversy (1994)

Madonna’s 1994 appearance on The Late Show is nothing short of legendary for the chaos it caused. First of all, she dropped F-bombs, then offered Letterman her underwear, and to add insult, she poked fun at his personal life. This interview became one of the show’s most censored and talked-about episodes for decades to come.

3. Nicole Kidman – The Cringe That Broke the Internet (2015)

Back in 2015, Nicole Kidman said something on The Tonight Show that later went viral for its sheer awkwardness. The actress casually confessed she once had a crush on Jimmy Fallon, going as far as to recount a visit to his apartment where he failed to notice she was flirting. Fallon’s reaction quickly became a meme and took over the Internet.