Cameron Diaz

Cameron Diaz was a mainstay in Hollywood in the 1990s, so it’s not shocking that she’s had her fair share of fame and investments. The actress is married to rocker Benji Madden, with whom she married in 2015. Even though their relationship was unexpected, they soon established themselves as one of Hollywood’s most powerful couples. However, Cameron’s love life has been a long and winding road to the happiest place she’s ever been with her husband.

Long before she reached the peak of her career, she had a brief friendship with video producer Carlos De La Torre, whom she met during a commercial shoot. The day after, Carlos called her, and the two hit it off immediately. They lived together for a while before breaking up in 1994. She’s dated other actors, including Matt Dillon and Jared Leto, since her breakthrough role in The Mask, and she’s even dated one of NSYNC members. The actress was also linked to athletes such as a major league baseball player and a surfer.