When it comes to Sheryl Crow’s relationships, she may be best-known for her long-term love and subsequent broken engagement from cyclist Lance Armstrong, but back at the turn of the millennium, she also put in a good stint with another big name: Owen Wilson. The relationship between the singer, then 38, and the actor, then 30, might get overlooked in the grand scheme of things, but it was serious enough for her to write a song about him when they split. Let’s find out what happened …

How it Began

Already a big name in music, Crow made her movie debut in 1999 thriller The Minus Man — and in the movie, she’s murdered by a serial killer, played by Wilson. IRL, the pair got along a lot better, and started dating. And they were seemingly proud to be seen together, PDA-ing on the red carpet at

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