Sheryl Crow's Dating History Is Packed With Celebs: All The Famous Men She's Dated

Sheryl Crow's stunning net worth is from a music career filled with success.  The singer-songwriter has won nine Grammy Awards, had seven songs that charted in the top 10, and sold over 50 million albums worldwide. In 2023, the "Strong Enough" singer was inducted into the Rock & Roll Hall of Fame. 

Today, Crow is a single mom with two adopted sons. She didn't imagine that she would be raising kids on her own. "To be able to just say, you know what, I feel a motherly instinct and desire for children and I'm gonna row the boat halfway and we'll see if it comes and meets me, and it did ... Sometimes taking your perception of the way you think your life is supposed to look, taking that out of the picture really does create so much incredible opportunity," she told Yahoo Entertainment. 

But what about Crow's romantic happily ever after? The truth about Sheryl Crow's dating history is that despite three engagements, the pop singer has never walked down the aisle. "Hey, I would love to get married — I'm still old-fashioned. But I don't think marriage is the be-all and end-all," she told Good Housekeeping (via People). "It's better to have three broken engagements than three divorces." For Crow, dating celebrity men has had its downsides. "[W]hat ends up happening is that one of you becomes smaller — and it was always me," added Crow. "I do think that sometimes in order for one person's light to shine, everyone else has to dim theirs."

In 1992, Kevin Gilbert brought his girlfriend, a then-unknown Sheryl Crow, to join a group of other musicians who jammed every Tuesday night in Los Angeles. They dubbed the jam night the Tuesday night sessions, and the group wound up crafting and playing on Crow's debut album, "Tuesday Night Music Club." The album went on to sell over 5 million copies stateside and win three Grammy Awards on the strength of three top-charting singles: "Leaving Las Vegas," "Strong Enough," and "All I Wanna Do." It also made Crow a bona fide superstar.

Unfortunately, when it came time to tour the hit record, Crow opted not to use the studio musicians from the Tuesday night sessions. There was also controversy over songwriting credits; the Tuesday night crew felt that they were not given proper credit for the contributions they made to the album, especially the song "Leaving Las Vegas." Crow and Gilbert broke up as her star rose. "I don't know if I can ever forgive her," Gilbert wrote in his journal (via SFGATE). "I don't hate her — I'm just soooo disappointed."

In 1996, 29-year-old Gilbert died under accidental circumstances. "I saw something in Entertainment magazine that said Kevin Gilbert, the piano player on Sheryl Crow's record, had died," said David Baerwald, a member of the Tuesday night sessions. "He hated that Sheryl Crow record and that's all he's going to be known for. The piano player? Roll over, Kevin Gilbert."

Sheryl Crow and Eric Clapton dated in the late 1990s. By the end of the decade, Crow was a massive, internationally acclaimed singer-songwriter. In 1998, she released her third album, "The Globe Sessions." The first single, "My Favorite Mistake," depicts an unfaithful ex.

"Now, here comes your secret lover/She'll be unlike any other/Until your guilt goes up in flames/Did you know when you go, it's the perfect ending/To the bad day, I'd gotten used to spending/When you go, all I know is you're my favorite mistake" (via Genius).

The radio-friendly pop song peaked at No. 5 on Billboard's Mainstream Top 40 chart. It also won Crow a Grammy Award for best female pop performance. After the song became a hit, there was speculation that it was written about her relationship with Clapton. Crow denied the rumor. The topic came up again in 2023 when Crow compared her hit tune to one of the most famous rock mysteries. "It's still so personal to me that I don't know that anybody knows who it's really about," Crow told People. "I guess it's my 'You're So Vain' moment — I Carly [Simon]-ed it," added Crow. "People thought it was [about Clapton] because I had been dating him for a little bit; I love Eric, and I admire him, but the song was older than that." Clapton and Crow have remained on good terms and have even performed the song live together.

Owen Wilson as a serial killer? The usually affable actor took the role of a polite but deranged serial killer in the drama "The Minus Man." The character kills unhappy people, whom he thinks he's helping. His first victim was a junkie played by Sheryl Crow in her cinematic debut. Despite their characters' conflict, Crow and Wilson started dating and became one of the It couples of the late 1990s and early 2000s. 

Their courtship ended after a two-year run. The truth about Sheryl Crow and Owen Wilson's relationship can be seen, at least from the singer's point of view, in the 2002 breakup song "Safe and Sound" off her fourth studio album "C'mon, C'mon." Crow notes in the song's credits, "For O." She sings during the outro of the song, "Feel like I should've heard you/Feel like I could have healed you/(Until you're safe and sound)/Feel like I could have changed you/Feel like I could've heard you" (via Genius).

Wilson lamented the end of his relationship with the "Soak Up the Sun" singer in a 2005 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" (via Us Weekly).

After Sheryl Crow's relationship with Owen Wilson ended, the musician started dating another actor, Josh Charles. "The Good Wife" star and the "All I Wanna Do" singer publicly announced their relationship by walking the red carpet together at the Grammys in 2003, where she was nominated for five awards. 

However, the pair's courtship only lasted a couple of months. The real reason Sheryl Crow and Josh Charles broke up seems to be because of their age difference and different stages of life. Crow was 41 at the time and looking to start a family, while Charles was a decade younger. 

Crow eventually stopped waiting to find the perfect partner to start a family with and opted to adopt as a single mom. In 2007, the Grammy winner adopted Wyatt Steven. Three years later, she adopted another son, Levi James. "It wouldn't have been my first choice to do it by myself," Crow told Yahoo Entertainment in 2020. "But to be perfectly honest, I feel like the way that my life has — I keep saying the way that it rolled out, but it really is true — the way things have happened for me have not been conventional." Sheryl Crow's sons are growing up fast without the added pressure of being in the spotlight. The singer moved to Nashville so that they could be away from the hoopla of Los Angeles.

What's the real reason Sheryl Crow and Lance Armstrong broke up? After splitting from Josh Charles because she wanted to start a family, the singer began dating the famed cyclist. The pair met at a charity event in 2003, and it was love at first sight. "I knew pretty quickly that I was totally into him," Crow admitted to People. 

The couple got engaged in 2005. It would have been Crow's first marriage. Armstrong had three kids with his first wife, whom he divorced in 2003. "I love them as much as if they were my own," Crow told Entertainment Weekly. But the relationship wasn't built to last, and Armstrong and Crow announced their separation in 2006. Then, just a week later, the pop singer shared that she had been diagnosed with breast cancer. "When I was diagnosed and my relationship fell apart, people were camped outside trying to get that picture of Sheryl Crow at her lowest moment. I just lost all faith in humankind," she told People in 2019. 

Crow was able to get over her heartbreak and beat cancer. After she adopted her kids and moved to Nashville, she found a new level of contentment. "In the last 10 years I have come into contact with the person I was born as before all of this craziness, and I feel more in touch with the small-town girl from Missouri," Crow added. 

By 2011, a then-49-year-old Sheryl Crow had adopted two children but had kept her heart open to discovering romantic love. She found a new partner within her own touring band, musician and producer Doyle Bramhall II. Bramhall also co-produced her album "100 Miles From Memphis." "We have a great foundation, having known each other for 15 years," said Crow (via CBS News). "I've been in the situation where I've been involved with people and their kids, and if the relationship doesn't work out, it's heartbreak."

There isn't a lot of public information about Crow and Bramhall's relationship. However, we know that by 2014, the pair had split. At least publicly, the singer has not had a romantic partner since Bramhall. But Crow seems perfectly content with not getting married, despite getting engaged three times. 

"I go, 'Thank you God. Thank you. I didn't get married,'" she said on "The Howard Stern Show" in 2022 (via Yahoo Life). "I got breast cancer at the end of one relationship and it was horrible but when I came through it, I was like, 'You know what? I'd still be in that relationship had I not had breast cancer.' So in a weird way, I'm grateful. And you think you're gonna be like, 'Oh, F that guy,' or whatever, but by the time you get to that point, you've moved on and you don't really care anymore."