7. Ashton Kutcher and January Jones
Dated: 1998-2001
Before the whole Kutcher/Demi Moore fiasco, and before he even dated the late Brittany Murphy, the former Mr. Trucker Hat was linked to January Jones, a then-budding actress who hadn’t gotten her breakout role yet. Allegedly, Kutcher didn’t believe Jones would have success as an actress and discouraged her from pursuing her dreams. Years after the two split, Jones landed Mad Men.
8. Tyra Banks and Will Smith
Dated: 1993-1994
When they dated, Will Smith and Tyra Banks seemed like the dream power couple. He was the huge crossover star and she was one of the biggest models of her generation. Considering how differently the two have grown up—he, the composed A-list Hollywood actor and she, the eccentric host of America’s Next Top Model—the thought of them together would seem like nothing more than a crazy PR stunt.
9. Tom Cruise and Cher
Dated: 1986
This pairing makes us wish there were a reality TV show that paired the weirdest characters in Hollywood together and sent them on dates. The Tom Cruise and Cher episode would be absolutely hilarious. First of all, there’s the 16-year age gap. Second of all, there’s the transparent, glittery outfit Cher would likely wear and Tom’s reaction to it—probably a flash of his winning smile, the one that usually conceals all the batshit crazy ideas circling around inside. Finally, there’s their conversation. Would she give him tips on how to dress to reinvent himself post-divorce? Would he try to recruit her into The Church? We’ve never wished for a time machine so badly.