Hollywood's 20 Oddest Couples Of All Time

Love knows no boundaries, especially in Hollywood.

In the wake of Katy Perry and Russell Brand‘s, we’re celebrating the day of love with a look back at some past couples that seriously raised eyebrows. Although most are now history, a few are still going strong. We’re talking to you, Katie Holmes and Tom Cruise.

From McCaulay Culkin and Mila Kunis to Michael Jackson and Lisa-Marie, here are 20 celebrity couples that made us do a double take. 

50 Cent and Chelsea Handler: One of the most unexpected hookups was Handler's short-lived romance with rapper 50 Cent. The two met when he appeared as a guest on her show.

Brad Pitt and Juliette Lewis: Before Angelina, Brad dated Lewis for four years while she was a teen. We're glad to see Brad with his leading lady.

Paris Hilton and Leonardo DiCaprio: OK, they were never officially reported a couple, but many media outlets pinned them together shortly after Hilton's split from Doug Reinhardt.

Courtney Stodden and Doug Hutchison: When news broke of the marriage between the now 17-year-old blonde bombshell and 51-year-old actor Doug Hutchison nearly everyone questioned the relationship's real intentions.

Tom Cruise and Katie Holmes: Cruise makes our list twice for his unexpected romance with 16-year younger Katie Holmes. Few would have expected their marriage to last with an engagement announced after only two months of dating.

Calista Flockhart and Harrison Ford: A 22-year age difference doesn't mean anything. After more than eight years together, the third time was the charm for Ford when the couple married June 2010.

Ashton Kutcher and Demi Moore: The 15-year age difference outlasted raised eyebrows throughout the length of their six-year marriage before Kutcher's cheating scandals led the couple to divorce.

Barbara Hershey and Naveen Andrews: The Lost actor dated actress Hershey on and off again for 11 despite a 21-year age difference and working through Andrews fathering another woman's child. The couple split up in 2009.

Woody Allen and Soon-Yi: Talk about family drama. After a 12-year marriage to Mia Farrow, Allen surprised everyone by getting together with her daughter. The two share a 35-year age difference.

Drew Barrymore and Tom Green: After meeting in 2000, the couple tied the knot the following July only to file for divorce five months later. Currently, Barrymore is engaged to Will Kopelman.

Madonna and Dennis Rodman: Madonna may have been with Warren Beatty, and Rodman with Carmen Electra, but this relationship takes the cake. Rodman claimed that Madonna wanted to have his children so badly that she once asked him to fly across the country for a late-night get together.

You've seen Cruise's weird romances, now check out his box office winners.

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