57. Drew Barrymore & Tom Green

This may come as a surprise to some, but Drew Barrymore was once married to Tom Green. After the Golden Globe-winning actor signed on to produce and star in the 2000s film Charlie’s Angels, she crossed paths with the comedian, who she wanted to feature in the movie. He was eventually cast as The Chad. “She and the studio were trying to get me in that movie for a while,” Green said on The Alan Cox Show in 2018. “I actually passed on it initially.” After agreeing to be in the movie, the two began dating. The couple got engaged and tied the knot in July 2001. They separated in December of that year.

Although Barrymore and Green’s marriage was one of Hollywood’s most compelling celebrity marriages, the Charlie’s Angels star believes she and her former husband were “idiots” for tying the knot when they did it. She explains that they were young, and she did not know how to handle things in her personal life. After not talking for 15 years, Barrymore and Green reunited in an episode of The Drew Barrymore Show. To their credit, they appeared to be on good terms with each other.