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Madonna & Keith Carradine, Madonna "Material Girl" (1985)
Madonna is said to have met her first husband, Sean Penn, on the set of this iconic video. But the role of her love interest went to Martha Plimpton's dad, known for his work on Deadwood and Dexter.
Paula Abdul & Keanu Reeves, Paula Abdul "Rush Rush" (1991)
Long before American Idol came calling, Abdul and the man who would become Neo enjoyed a Rebel Without a Cause-inspired romance for the cameras.
Eddie Murphy & Iman, Michael Jackson "Remember the Time" (1992)
Iman played the bored queen to Murphy's Pharaoh, though she's clearly much more interested in Michael Jackson.
Axl Rose & Stephanie Seymour, Guns N' Roses "November Rain" (1992)
The supermodel played Rose's doomed bride in this epic music video. She was dating the rocker in real life, but it remains one of those romances we still don't quite get.