1. Justin & Britney
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    A match made in denim
  2. Madonna & Sean Penn
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    Too cool. Best bad boy and bad gal pairing. Also if you have watched Truth or Dare you know that moment during a game of truth or dare where one of the dancers asks Madonna a truth- "who is the love of your life" and Madge, after a little pause just says. "Sean. Sean". I get chills just thinking about it. They'd been divorced for a while and she was dating someone else...check the next couple on this list.
  3. Madonna & Warren Beatty
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    Filming Dick Tracy made this unexpected yet riveting couple. If you haven't seen Truth or Dare, I don't really know what you're doing with your life, but one of the best parts of it is seeing Madonna's relationship with Warren slowly deteriorate--he just doesn't get her and it's awkward. WATCH TRUTH OR DARE.
  4. David Bowie & Iman
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    I don't need to explain why.
  5. J.Lo & Sean P. Diddy Combs
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    So fly. I'm still hoping these two get back together. Not kidding. If that shooting hadn't gone down in da club who knows where J and Diddy would be today....together?! 🙏
  6. Johnny Depp & Winona Ryder
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    Edward Scissorhands gets the girl.
  7. Anjelica Huston & Jack Nicholson
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    Obviously. The most chic. Too bad he strung her along the entire length of their relationship and wasn't the most devoted--the 70's amiright?