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when it comes to Sheryl Crow‘Of her relationships, she is perhaps best known for her long-term love and subsequent engagement to a cyclist Lance Armstrongbut she also spent some quality time with another big shot at the turn of the century: Owen Wilson. The relationship between the then-38-year-old singer and the then-30-year-old actor might have been overlooked in the grand scheme of things, but it was enough for her to write a song about him when they broke up. Let’s see what happens…
Crow was already a big name in the music industry, having made her film debut in the 1999 thriller negative sign person —In the movie, she is murdered by a serial killer played by Wilson. In reality, the two got along much better and started dating. They seemed proud to appear on the red carpet together at various events including 2000 vanity fair Oscar party.
Despite their obvious chemistry, within two years the relationship ended.

Sheryl Crow and Owen Wilson, 2000
Steve Granitz/WireImageWhile their relationship was fairly public while it lasted, the breakup was private, with neither party commenting at the time. However, in the years since, a picture has been formed of what happened between them – not least through the song “Safe and Sound” that Crowe seemingly dedicated to Wilson.

Sheryl Crow and Owen Wilson, 1999
Steve Eichner/Getty ImagesOn “Safe and Sound,” from Crow’s fourth album, C’Mon C’Mon, released in 2002, Crow seemed to sing about the relationship (yes, taylor swift After all, she didn’t invent the song about her famous ex! ) “Releasing is beautiful and there’s no one to please but you and me,” she sings, which Billboard described as “a hauntingly beautiful breakup song.” The lyrics continue: “Feel like I can hold on, feel like I can let go, feel like I can help you, feel like I can change you, feel like I can love you, feel like I really love you, feel like I can save you.”
In 2005, Wilson also expressed his views in an interview playboy. “The story of our relationship is the same story I’ve been through in most relationships,” he said. “I was lucky enough to find a wonderful girl, but our relationship failed due to my lack of… focus.”
He added: “Going out with someone in the public eye who does the same thing as you can be a problem. You go home and want to take a break. You don’t want someone to have the same issues as you and remind you of things you don’t like. That being said, I don’t think being in the spotlight has anything to do with Cheryl and I not working out.”

Sheryl Crow and Owen Wilson, 2003
Jeff Vesper/WireImagIn 2014, Crow and Good housekeeping service About how she now avoids relationships with celebrities after all these high-profile breakups. “I’ve always been associated with very successful people, and that seemed to put me on an equal footing,” she said. “But what ends up happening is, one of you gets smaller — and it’s 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 their light.”
In 2020 — and a number of relationship breakdowns later — Crowe, a breast cancer survivor, was also linked to Dax Shepard“Armchair Expert” podcast about her relationship patterns. “I’m not going to let anyone take care of me,” she said. “I don’t let anyone build me up. I’m the adjuster in all my relationships. I think I’ve really mastered, even within a relationship, choosing someone who can really embody that with me and allow me to really be the one at the bottom.”

Sheryl Crow and Owen Wilson, 1999
Kevin Mazur/WireImageCrowe and Wilson both became single parents in the years following their split, with the singer adopting two sons and the actor having three children with three different women.
They were both unmarried and had a reputation for being a bit unlucky in love – or, in Wilson’s case, not really the settled type. Whether their relationship greatly affected their lives is a mystery, but it at least spawned a pretty solid breakup song.