Rupert Everett says flop movie with Madonna put 'strain' on their friendship, 'finished' him in Hollywood
Published on December 01, 2025 EDT

Rupert Everett says his relationship with Madonna — and his Hollywood career — never recovered after they starred in The Next Best Thing together.

The Importance of Being Earnest actor recently reflected on his experience working with the pop superstar on the 2000 romantic dramedy. "Friendships and failure in Hollywood are very difficult things to keep going," Everett said, looking back at the movie's critical flogging on the latest episode of the podcast How to Fail With Elizabeth Day.

He added that the film "was definitely a strain" on his friendship with Madonna. When asked if he'll ever reconnect with the singer, he replied, "Well, possibly. I don't know."

Paramount/Courtesy Everett Collection

The British star sympathized with the scrutiny that Madonna faced as an actress. "I think it's very difficult for her to be in films because everyone has such a preconception," Everett said. "And I don't know how she could ever be good enough to make people say, 'Oh, God, that's really good.' I think it was great having her in the film."

The Next Best Thing follows a gay man who inadvertently conceives a child with his female best friend (or does he?) — and although Everett refers to it as a "car crash," he still believes it was a financial success thanks to his costar. "Madonna sold a lot of [home] videos," he said. "But the film itself didn't work."

While he admires her performance in the movie, he doesn't revisit it often. "I think she was touching in the film, too, myself. I haven't seen it for ages, though. I mean, every time that comes on, I kind of look the other way."

Paramount/courtesy Everett Collection

Elsewhere in the interview, Everett said the film's underwhelming reception stung extra hard because he was the main reason it existed in the first place. "The sad thing about The Next Best Thing was that it really was my movie," he said. "It came to me after [1997's] My Best Friend’s Wedding. I was very popular in Hollywood for that year. It was made by Paramount. The movie was greenlit because I was going to be in it."

The actor partially blamed himself for its subpar execution, as he and his writing partner rewrote the script. "I also hired John Schlesinger to be the director, which was, I think, in hindsight, where it was a mistake, because then he wanted me to stay with him and help him prepare the movie and I went off and did another job," Everett said regretfully. "That was an example of me not really following the ball exactly, because possibly I could have stayed with him during the preproduction and structured the film as I thought it should have been."

The movie "rapidly flew out of control," Everett recalled. "At a certain point, I remember I was fired as the writer, fired as the producer, and the producer said to me, 'If you want to stay as the actor, you can, but don't if you don't want to.' I should have probably walked away from it at that point and I didn't."

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Paramount/Courtesy Everett Collection

Everett also credits the film with destroying his career momentum in the U.S. "Everything went wrong, really, in the making of it. And it completely finished things for me in Hollywood," he said. "I was very much enjoying my Hollywood revival. And like all idiots, I thought it was just going to go on forever and then it didn't. So it was difficult to adapt to."

Listen to the full conversation between Everett and Day above.

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