Nicole Kidman visited Jimmy Fallon on ” The Tonight Show” in 2015. The last time they met was on a 2002 date. Yes, you read that correctly; Fallon was set up on a date with the A-lister bombshell. A mutual friend brought her over to Fallon’s place. Kidman and Tom Cruise were on the splits at the time. Fallon didn’t know that either.
He never knew it was an actual date. She explained that she wasn’t interested because he ignored her and played video games. Then she speculated that Fallon didn’t like women. Fully mortified, Jimmy briefly walked off his own show.
Jay Leno
Before he has his own show, David Letterman would occasionally act as a guest host for "The Tonight Show," between 1978-1980. In 1982, Letterman would spread his wings on his own show, "Late Night with David Letterman." Ironically enough, Letterman welcomed future "Tonight Show" host Jay Leno as a guest.
At the time, Leno was a regular on the stand-up comedy circuit, slowly transitioning to a number of minor roles in film and television. As Carson retired in 1992, fans were sure Letterman was next in line to take over "The Tonight Show," yet lo and behold, the role when to Leno, who hosted until 2009!
Emma Watson
The most awkward moment on late night television that Emma Watson ever experienced happened on Jimmy Fallon’s show back in 2012. She joined him at the desk and broke in with a compliment on the ‘Halloween candy thing.’
The Halloween candy thing is a skit performed by late-night show fans who taped their children’s reactions when it was explained to them their parents had eaten all their candy. It was very brutal and very funny; Leno dissed it for cruelty. But Watson apparently loved it. Unfortunately, Jimmy Kimmel’s show did that bit, and Watson was facing Jimmy Fallon, absolutely mortified.
Robin Williams
Robin Williams is epic in every interview he ever gave. In 1998 he was on key with David Letterman. Letterman quizzed him about his friendship with sitting President Bill Clinton, and the exchange was hilarious.
When it got to the point of his visit to promote "Good Will Hunting," Williams spoke of the film endearingly; he clearly loved the project. “I got this amazing script, I agreed to do it, and then, all the sudden, I meet [Ben Affleck and Matt Damon] on the set.” Then unknowns, Williams joked about asking to see their ID and if they had their father’s permission.
Drew Barrymore
Recently, Drew Barrymore admitted that her performance on David Letterman’s show in 1995 was a TMI moment that she had learned from. She was 20 and had already been in the entertainment industry for more than a decade. She said she didn’t regret it because it was fun, but here’s what happened.
Barrymore asks Letterman if he’d like her to table dance for him. Paul Shaffer provided some bluesy music. Just before her dance on his desk ends, she flashes him really quickly and returns to her seat. Letterman meant it when he said, “I can’t thank you enough for that.”