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.
4. Hugh Grant – A Career Redemption (1995)
Many of us still remember that scandalous story from 1995 about Hugh Grant and a sex worker fooling around in a public place. He did get arrested for that but shortly after appeared on The Tonight Show with Jay Leno. Instead of avoiding the truth, Grant swiftly confronted the pressing issue and candidly acknowledged his wrongdoing. His honesty and humility turned a PR disaster into a late-night redemption story and won over skeptical fans.
5. Paris Hilton – The Comeback Queen (2007)
Paris Hilton’s 2007 interview with David Letterman on The Late Show became a viral sensation for all the wrong reasons. Fresh out of jail, Hilton was there to promote her perfume, but Letterman kept poking at her recent incarceration. The awkward tension was palpable as Hilton maintained her composure while Letterman pushed the envelope.
6. Harrison Ford – Breaks Han Solo Toy (2010)
Harrison Ford’s dry humor always shines on late-night shows, and his Conan appearances are no exception. In a 2010 interview, when Conan asked him to sign a Han Solo figurine, Ford quipped, “Get a life.” His perfect deadpan delivery turned what could’ve been a generic Q&A into a comedic highlight.
7. Joaquin Phoenix – Master of Mystery (2009)
Joaquin Phoenix’s bizarre interview on The Late Show with David Letterman in 2009 had viewers scratching their heads. Disheveled, mumbling, and donning sunglasses, Phoenix seemed disinterested as he promoted a supposed new rap career. It turned out to be an elaborate stunt for his mockumentary I’m Still Here, but we will never forget that uncomfortable vibe.
8. Drew Barrymore – A Risqué Surprise (1995)
Drew Barrymore made headlines during her 1995 appearance on The Late Show with David Letterman when she climbed onto his desk and flashed him (as a joke, of course). Letterman’s stunned but delighted reaction added to the moment’s charm, and it became one of the most iconic late-night moments of the decade.
9. Heidi Klum – Hidden Talent (2017)
Heidi Klum’s aura is unmatched, and her 2017 appearance on The Late Show With Stephen Colbert showed off her incredible, almost inhuman ability. The model can apparently control when and where she sweats. Heidi has mastered her perspiration for the sole purpose of avoiding the need to powder her face every 30 minutes when she’s on camera. According to Klum, she simply tells herself not to sweat in a specific area, such as her face, and to sweat in places where people can’t see it.
