In relation to Sheryl Crow’s relationships, she could also be best-known for her long-term love and subsequent damaged engagement from bicycle owner Lance Armstrong, however again on the flip of the millennium, she additionally put in a great stint with one other massive title: Owen Wilson. The connection between the singer, then 38, and the actor, then 30, may get ignored within the grand scheme of issues, however it was critical sufficient for her to put in writing a music about him once they cut up. Let’s discover out what occurred …
The way it Started
Already a giant title in music, Crow made her film debut in 1999 thriller The Minus Man — and within the film, she’s murdered by a serial killer, performed by Wilson. IRL, the pair received alongside rather a lot higher, and began courting. They usually have been seemingly proud to be seen collectively, PDA-ing on the pink carpet at occasions together with the 2000 Vainness Honest Oscar get together.
How Lengthy it Lasted
Regardless of their apparent chemistry, inside two years the connection was over.
The way it Ended

Sheryl Crow and Owen Wilson in 2000 Steve Granitz/WireImage
Whereas their relationship was fairly public whereas it lasted, the cut up was personal, with neither get together commenting on the time. Nevertheless, within the years since, an image has fashioned of what went down between them — not least through the music Crow appeared to dedicate to Wilson, “Secure and Sound.”
What They Stated About Every Different

Sheryl Crow and Owen Wilson in 1999 Steve Eichner/Getty Photos
In “Secure and Sound”, from Crow’s fourth album “C’Mon C’Mon,” launched in 2002, Crow seemingly sings concerning the relationship (yup, Taylor Swift didn’t invent singing about well-known exes in any case!) “There’s magnificence in launch, there’s nobody left to please, however you and me,” she sang, in what Billboard described as a “hauntingly lovely break up music.” The lyrics went on: “Really feel like I might’ve held on, really feel like I might’ve let go, really feel like I might’ve helped you, really feel like I might’ve modified you, I really feel like I might have beloved you, I really feel like I actually love you, really feel like I might’ve saved you.”
In 2005, Wilson additionally had his say, in an interview with Playboy. “The story of our relationship is similar story I’ve had with most relationships,” he mentioned. “I used to be fortunate sufficient to search out an incredible woman, and due to my lack of… focus, the connection went south.”
He added: “Going out with somebody who’s doing the identical factor as you, who’s within the public eye, could be a drawback. You desire a break if you come residence. You don’t need somebody with the identical points as you reminding you of stuff you don’t like in your self. That being mentioned, I don’t assume being within the highlight had something to do with me and Sheryl not figuring out.”
What They Say Now

Sheryl Crow and Owen Wilson in 2003 Jeff Vespa/WireImag
In 2014, Crow spoke to Good Housekeeping about how she was now avoiding movie star relationships following all these high-profile breakups. “I had all the time gone out with guys who have been extremely profitable, which would appear like it could put me at an equal degree,” she mentioned. “However what finally ends up taking place is that one in every of you turns into smaller — and it was all the time me. It’s all the time the lady. I imply, I don’t know if it’s all the time the lady, however I do assume that typically to ensure that one particular person’s gentle to shine, everybody else has to dim theirs.”
In 2020 — then a couple of extra relationships down, and as a breast most cancers survivor — Crow additionally spoke to Dax Shepard’s “Armchair Skilled” podcast about her relationship patterns. “I wouldn’t let anybody maintain me,” she mentioned. “I wouldn’t let anybody nurture me. I used to be the fixer in all my relationships. I believe I had actually mastered, even in a relationship, choosing somebody that would actually manifest that with me, of constructing me severely the underside of the heap.”

Sheryl Crow and Owen Wilson in 1999 Kevin Mazur/WireImage
Key Relationship Takeaways
Each Crow and Wilson have grow to be single mother and father within the years since their cut up, with the singer adopting two sons, and the actor fathering three youngsters with three completely different girls.
In addition they each stay single, with reputations for being just a little unfortunate in love — or, in Wilson’s case, simply probably not the settling down kind. Whether or not their relationship influenced their lives dramatically is a thriller, however it did at the least spawn a fairly stable breakup music.

