Simon Cowell’s Funniest Moments on Late Night Television

Corey Cesare
Pablo Urdiales Antelo
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Simon Cowell has been a household name ever since he joined the iconic Idol franchise. He’s now one of the biggest moguls on TV. Along the way, he’s had some pretty hilarious interviews on late night’s greatest talk shows. Here are a few of our favorites.


1. He Banters With Demi Lovato on CONAN

There’s no denying that Cowell and Lovato had great chemistry while working together on The X Factor. This late night talk show appearance showed off their banter in the best way possible. They began by mocking Cowell’s leisure outfit, then turned the topic to which judge was more annoying.

The comment that had us giggling the most was CONAN’s statement to end the bantering:

“Don’t pick on him, he’s a kind man who’s never insulted, anyone.”


2. Cowell Learns That He Has Two Parking Spaces

In typical late night talk show fashion, Craig Ferguson poked fun at Cowell in the best ways possible. The talk show host began the second half of the show by talking about how television mogul used to get two parking spaces at the CBS studios. Cowell explained that he had a large car, but also had no idea he got two places.

Together, they made fun of the original fourth judge of American Idol, Kara DioGuardi. He explained his hatred of DioGuardi and Paula Abdul’s elaborate stories on the set. This lead the talk show host to asked if Cowell would be getting married anytime soon, “since most women are like that.”

3. He Admits That He Hates Dora The Explorer

In 2016, Cowell joined The Tonight Show With Jimmy Fallon to talk about his relationship with his son. After admitting that he thought his son hated him at first, the talent show mogul went on to share the reason he hates a lot of children’s shows. It comes as no surprise that Cowell doesn’t get along with Dora Explorer due to the fact that he doesn’t like the music.


“After that three months, Dora’s gone on a long holiday and has gone lost and won’t be coming back,” Cowell said.

4. Jonathan Ross Pokes Fun at Cowell and Walliams Bromance

There’s no denying that Cowell and David Walliams have great chemistry on Britain’s Got Talent. While these two are typically fun to watch on the talent series, their personalities truly came out on this late night show. The majority of the conversation was about the BGT judges apparent bromance. Jokes were all about Cowell’s sexuality and the fact that Walliams preferred to sit close to his friend.

On top of being funny, this late night talk appearance shows how different Cowell truly is in modern day. In modern day, the television mogul is engaged to his longtime girlfriend, Lauren Silverman. Beginning remarks place emphasis on how Walliams had just gotten married, but Cowell had no such plans in the future.

5. A Couple Offered Him Money to Judge Their Sex

Since Cowell has been in the judging business for quite some time, it’s no surprise that people on the streets ask if he can judge their talents. Within his late night appearance, he admits that a couple once asked him to judge their intercourse for $150,000. The talent show mogul joked saying that he wouldn’t turn down the offer again.

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