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 events including the 2000 Vanity Fair Oscar party.
How Long it Lasted
Despite their obvious chemistry, within two years the relationship was over.
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How it Ended
While their relationship was pretty public while it lasted, the split was private, with neither party commenting at the time. However, in the years since, a picture has formed of what went down between them — not least via the song Crow appeared to dedicate to Wilson, “Safe and Sound.”
What They Said About Each Other
In “Safe and Sound”, from Crow’s fourth album “C’Mon C’Mon,” released in 2002, Crow seemingly sings about the relationship (yup, Taylor Swift didn’t invent singing about famous exes after all!) “There’s beauty in release, there’s no one left to please, but you and me,” she sang, in what Billboard described as a “hauntingly beautiful break up song.” The lyrics went on: “Feel like I could’ve held on, feel like I could’ve let go, feel like I could’ve helped you, feel like I could’ve changed you, I feel like I could have loved you, I feel like I really love you, feel like I could’ve 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,” he 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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He added: “Going out with 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 come home. You don’t want someone with the same issues as you reminding you of stuff you don’t like in yourself. That being said, I don’t think being in the spotlight had anything to do with me and Sheryl not working out.”
What They Say Now
In 2014, Crow spoke to Good Housekeeping about how she was now avoiding celebrity relationships following all those high-profile breakups. “I had always gone out with guys who were highly successful, which would seem like it would put me at an equal level,” she said. “But what ends up happening is that one of you becomes smaller — and it was always me. It’s always the woman. I mean, I don’t know if it’s always the woman, but I do think that sometimes in order for one person’s light to shine, everyone else has to dim theirs.”
In 2020 — then a few more relationships down, and as a breast cancer survivor — Crow also spoke to Dax Shepard’s “Armchair Expert” podcast about her relationship patterns. “I wouldn’t let anyone take care of me,” she said. “I wouldn’t let anyone nurture me. I was the fixer in all my relationships. I think I had really mastered, even in a relationship, picking someone that could really manifest that with me, of making me seriously the bottom of the heap.”
Key Relationship Takeaways
Both Crow and Wilson have become single parents in the years since their split, with the singer adopting two sons, and the actor fathering three kids with three different women.
They also both remain unmarried, with reputations for being a little unlucky in love — or, in Wilson’s case, just not really the settling down type. Whether their relationship influenced their lives dramatically is a mystery, but it did at least spawn a pretty solid breakup song.
