Sheryl Crow wrote a breakup song for Owen Wilson after the breakup

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

How it started

Already a big name in music, Crow made his film debut in 1999 in a thriller The Man Less – and in the film, she is killed by a serial killer, played by Wilson. IRL, the pair got along much better and started dating. And they were apparently proud to be seen together, PDA on the red carpet at events including 2000. Vanity Fair Oscar party.

how long did it last

Despite their obvious chemistry, within two years the relationship ended.

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how did it end

While their relationship was quite public while it lasted, the split was private, with neither party commenting at the time. However, in the years since, a picture of what happened between them has been formed, most notably through the song that Crow appeared to dedicate to Wilson, “Safe and Sound.”

What they said about each other

On “Safe and Sound,” from Crow’s fourth album “C’Mon C’Mon,” released in 2002, Crow appears to be singing about the relationship (yes, taylor swift he didn’t invent singing about famous exes after all!) “There’s beauty in liberation, there’s no one left to please but you and me,” she sang, in what Billboard described as a “breakup song of haunting beauty.” The lyrics continued: “I feel like I could have held on, I feel like I could have let go, I feel like I could have helped you, I feel like I could have changed you, I feel like I could have loved you, I feel like I really love you, I could have saved you.”

In 2005, Wilson also had his say, in an interview with playboy. “The story of our relationship is the same story I’ve had with most relationships,” she said. “I was lucky enough to find a great girl, and because of my lack of… focus, the relationship went south.”

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She added: “Dating someone who’s doing the same thing as you, who’s in the public eye, can be a problem. You want a break when you get home. You don’t want someone with the same problems to remind you of things you don’t like about yourself. That said, I don’t think being in the spotlight has anything to do with me and Sheryl not working out.”

What they say now

In 2014, Crow spoke with Good cleaning about how she was avoiding celebrity relationships after all those high-profile breakups. “I had always dated guys who were very successful, which seems like it would put me on the same level,” she said. “But what ends up happening is one of you gets smaller, and it’s always been me. It’s always the woman. I mean, I don’t know if it’s always the woman, but I think sometimes in order for one person’s light to shine, everyone else has to dim theirs.”

In 2020, after a few more low-key relationships and as a breast cancer survivor, Crow also spoke to Dax ShepardThe “Armchair Expert” podcast about your relationship patterns. “I wasn’t going to let anybody handle me,” he said. “I wouldn’t let anyone feed me. I was the fixer in all my relationships. I think I had really mastered, even in a relationship, choosing someone who could really manifest that with me, to seriously become the bottom of the heap.”

Key takeaway relationships

Both Crow and Wilson have become single parents in the years since their split, with the singer adopting two children and the actor fathering three children with three different women.

Both also remain single, with a reputation for being a bit unlucky in love, or in Wilson’s case, just not the easygoing type. Whether their relationship dramatically influenced their lives is a mystery, but at least it spawned a pretty solid breakup song.