10 Surprising Celebrity Romances You Never Heard About

Because even people who don’t care about celebrities know every detail about Brangelina’s twins and Lindsay and Britney’s breakdowns, it’s hard to believe that any Hollywood romance could slip by unnoticed. There was, however, a time before the Internet and the paparazzi documented each misstep celebrities took, and it’s easy to forget the random hookups from the 80s and 90s. Some celebrity couples were so short lived, and even though they hooked up at a time when bloggers and tabloids are still on top of their game, those couples got lost in the hoopla surrounding Paris Hilton’s jail sentence, Jessica’s jinxing the Dallas Cowboys or some other celebrity scandal. To honor the pure randomness and scariness of these surprising couples, we’ve dug up our favorites from the Hollywood past.

  1. Sheryl Crow and Owen Wilson: We thought the only thing Sheryl Crow and Owen Wilson had in common was Kate Hudson, Owen’s ex who is now dating Sheryl’s ex, Lance Armstrong. As it turns out, Sheryl and Owen dated for three years, when Owen was just starting to make it in Hollywood with Shanghai Noon, Breakfast of Champions and Meet the Parents.
  2. Liam Neeson and Jennifer Grey: Liam Neeson dated Jennifer Grey?! We’ve always associated Liam Neeson as the kindly upstanding citizen and father figure from movies like Schindler’s List, Star Wars, Michael Collins and other major movies. While we thought Jennifer Grey was fantastic in Dirty Dancing and Ferris Bueller’s Day Off, we didn’t think the two were in the same league.
  3. Moby and Natalie Portman: Moby and Natalie Portman are both thoughtful vegans, but we’re still a little bit confused. Moby acknowledges that it was "a very brief affair," but is vague about when he and Queen Amidala hung out.
  4. George Clooney and Lucy Liu: If poor Lucy Liu got as much paparazzi credit when she dated George as current flame Sarah Larson does, she probably wouldn’t be on this list. George and Lucy were definitely a beautiful couple when they dated in 2000 and made out in 2006, but they certainly didn’t get the attention they deserved.
  5. Drew Barrymore and David Arquette: Before David found Courteney, he hooked up with then-still-a-little-too-wild Drew Barrymore. They’re both cute and kooky, but let’s not forget that they also played brother and sister in 1999′s Never Been Kissed.
  6. Brad Pitt and Christina Applegate: Back in the 80s and 90s, Brad Pitt dated Gwyneth, Juliette Lewis and…Christina Applegate? Christina was super hot stuff back then on Married With Children, but can a TV star really hold her own with a gorgeous movie star like Brad Pitt? Let’s rephrase that. Can a TV star hold her own against Brad Pitt if they aren’t at least Friends first? Since Christina and Brad only dated for a brief stint in 1988, we think not.
  7. Kimberly Stewart and Tommy Lee: Everyone knows Tommy Lee likes pretty blondes, and it’s probably only natural for Kimberly Stewart to go after rocker dudes, since her dad is Rod Stewart. What makes this story so weird is the fact that Rachel Hunter, Kimberly’s ex step-mom, also dated Tommy Lee. Kimberly and Tommy Lee briefly hooked up in 2007, when Tommy Lee was 44 and Kimberly was 26.
  8. Keaunu Reeves and Diane Keaton: Keanu Reeves and Diane Keaton were co-stars in the 2003 movie Something’s Gotta Give, but they started dating in 2005, when Keanu was 40 and Diane was 59. Does Diane still get to be a cougar if her beau is also nearing middle age?
  9. Reese Witherspoon and Stephen Dorff: This couple is one of the most bizarre items on our list. When Reese Witherspoon and Stephen Dorff dated in 1994, they were both young and blonde. In 2008, they still don’t have much more than that in common. Reese is one of the highest paid and most successful actresses in Hollywood, and Stephen Dorff is…sort of hot, but a major washout.
  10. Ashley Olsen and Lance Armstrong: It’s true that Lance Armstrong and Ashley Olsen’s 2007 hookup was documented in the tabloids, but it was so short lived that you may have missed it. Plus, it’s just weird. Lance is 15 years older than the former Full House shorty, which is still a pretty hefty age difference if you’re only 21. And what could the two possibly have had to talk about? Lance is a seven-time Tour de France winner, a cancer survivor and random BFFs with Matthew McConaughey and Owen Wilson. Ashley? Well she’s cute, fashionable and a multimillionaire. We guess it could work.