Sheryl Crow's Dating Track Record Is Packed With Celebrity Men

From "Strong Enough" and "If It Makes You Happy" to "My Favorite Mistake" and "The First Cut Is The Deepest," many of nine-time Grammy Award-winning singer-songwriter Sheryl Crow's biggest Billboard hits have been centered on affairs of the heart. And several equally famous men provided a source of inspiration during her commercial heyday.

Although Crow now appears to have been a proud singleton for over a decade, instead concentrating on bringing up her adopted sons Wyatt and Levi, she was something of a serial dater back in the '90s and '00s. So which classic guitarist and Hollywood funnyman were both reportedly immortalized on record after dating Missouri's finest? Which younger actor did she take as her date to the Grammy Awards? And how exactly did one romantic meal out leave a member of the Arquette family feeling like a third wheel? Here's a look at the celebrities who have been part of Crow's relationship history.

Sheryl Crow's first publicly known boyfriend was Kevin Gilbert, the man who helped steer her debut album "Tuesday Night Music Club" to multi-million, Grammy-winning success. However, by the time she took the record on the road, she'd dumped him both personally and professionally.

Crow's solo career path arguably began when Gilbert invited her to join a collective known as the Tuesday Music Club in 1992. It was here that the singer laid down the foundations for her breakthrough, with the pair writing several songs together, including "Leaving Las Vegas." But things started to turn sour when producer Bill Bottrell began to assert more creative control. "That started to cause real friction, and our relationship started deteriorating," Crow later said in the documentary "Sheryl" (via The Line of Best Fit).

That's backed up by one of the journal entries published following Gilbert's death in 1996. "I think I'm a tinge jealous over her upcoming release," he wrote (via SFGATE). "It's probably going to be huge so I have to prepare myself mentally for that. If she gets what she wants after behaving this way, she'll be absolutely intolerable." Things came to a head when Crow hired an entirely new band for the album's tour and many thought she was taking more than her fair share of credit for its success. "I don't know if I can ever forgive her," Gilbert wrote around the time. "I don't hate her — I'm just soooo disappointed."

In between her stint as Michael Jackson's backing singer and the release of her blockbuster solo album "Tuesday Night Music Club," Sheryl Crow penned songs that were picked up by several other artists including Celine Dion, Tina Turner, and the legendary guitarist known as "Slowhand," Eric Clapton. Although the latter didn't actually record the number in question, he did end up forging a more fruitful personal relationship with its songwriter.

Indeed, Crow briefly dated Clapton, 17 years her senior, in the mid-'90s. And the former appeared to address their fling with the lead single from her 1998 third LP "The Globe Sessions." "It's still so personal to me that I don't know that anybody knows who it's really about," she later told People about "My Favorite Mistake," the Top 40 hit in which she sings of a romance that ends in infidelity.

Crow has insisted that the track predated her romance with Clapton, but for many, he remains the prime suspect. Whether she had the former Cream frontman in mind or not, the pair still appear to be on good terms. A year later, Crow described (via E! News) Clapton as "a really good friend of mine" when she welcomed him onto the stage during a Central Park show. She also invited him to play guitar on her 2019 studio effort "Threads." 

Sheryl Crow and Owen Wilson certainly had a novel meet-cute. The unlikely pairing were first introduced to each other on forgotten 1999 thriller "The Minus Man," where the latter played a serial killer and the former one of his many victims. Still, despite this rather macabre origin story, the pair ended up dating for two years.

Unlike her previous dalliance with Eric Clapton, Crow was more than happy to show off Wilson, with the couple hitting the red carpet for various high-profile events including the Oscar party staged by Vanity Fair in 2000. So why did they call it a day? Well, in an honest interview with Playboy four years later, the "Midnight in Paris" actor admitted (via Us Weekly) that he was entirely responsible. "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."

Although Crow hasn't spoken publicly about their romance, she has alluded to it in song. On her 2002 album "C'Mon, C'Mon," she dedicated "Safe and Sound" to Wilson, a track whose heartfelt lyrics ("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") appear to back up Wilson's confession (via Genius).

As far as we know, Sheryl Crow hasn't written a song about her brief relationship with Josh Charles, the actor ten years her junior who at the time was best known for his roles in "Dead Poets Society," "Sports Night," and "Don't Tell Mom the Babysitter's Dead." In fact, neither party appears to have discussed the months they spent together in early 2003.

Crow did take Charles to the Grammy Awards ceremony that year, where she picked up best female rock vocal performance for "Steve McQueen." And they also headed out on a date to the MTV Rock The Vote 10th Annual Patrick Lippert Awards before going their separate ways. "They are no longer seeing each other," an insider explained to Us Weekly (via San Francisco Chronicle). "She's looking for The Guy, and he wasn't it."

According to other sources, the fact that Crow and Charles were at different stages of their lives was the contributing factor. Apparently, the former was ready to settle down and become a mom, and the latter wasn't yet interested in having kids. Of course, both parties went on to become parents, with "The Good Wife" star now a proud dad to two children with wife Sophie Flack and Crow adopting two sons, Wyatt and Levi.

Sheryl Crow looked to have found the one in the mid-'00s when she began dating, got engaged to, and moved in with Lance Armstrong, the multiple Tour de France winner who, at the time, was considered to be one of the greatest cyclists in sporting history. "I knew pretty quickly that I was totally into him," the singer gushed to People after meeting the athlete at a charity function in 2003.

Of course, both their relationship and Armstrong's reputation eventually ended up in tatters. "After much thought and consideration, we have made a very tough decision to split up," read a joint statement (via BBC News) in February 2006. "We both have a deep love and respect for each other and we ask that everyone respect our privacy during this very difficult time."

This "difficult time" was compounded when just a week later, Crow discovered she had breast cancer. Luckily, the "If It Makes You Happy" singer was treated successfully. Her former beau, of course, had also done the same after being diagnosed with testicular cancer. But his seemingly inspirational story took a dark turn in 2012 when he was ruled to have taken performance-enhancing substances by the U.S. Anti-Doping Agency. He subsequently was banned for life from the sport he'd made his name in, and although he initially protested his innocence, he eventually came clean — so to speak — in 2013.

Sheryl Crow found herself at the center of the tabloid mill again when she was linked to two very different celebrities with varying degrees of plausibility. Firstly, she was rumored to have stepped out with "American Idol" host Ryan Seacrest shortly after he'd been out on a date with "Desperate Housewives" star Teri Hatcher. However, evidence appears to be thin on the ground, with their only public connection the appearances Crow has made on the likes of "Dick Clark's New Year's Rockin' Eve with Ryan Seacrest."

Soon after, Crow was also gossiped about when she was seen enjoying dinner with Hank Azaria, the Emmy Award-winning actor then best-known for his multiple voiceover roles in "The Simpsons." New York Post reported (via LiveJournal) that despite also having "Medium" star Patricia Arquette for company, the pair "seemed to have eyes only for each other."

Whether there was any substance to these rumors or not, Crow later acknowledged why she stopped dating men in the public eye. "I have always gone out with guys who were highly successful, which would seem like it would put me at an equal level," she explained to Good Housekeeping (via People). "But what ends up happening is that one of you becomes smaller — and it was always me. I do think that sometimes in order for one person's light to shine, everyone else has to dim theirs."

After being linked to Ryan Seacrest and Hank Azaria in quick succession, Sheryl Crow then found herself in the gossip pages once again in 2008, this time for allegedly dating multi-millionaire entrepreneur Steve Bing. And apparently a friend was responsible for setting them up.

According to Star, Crow's celebrity pal Jennifer Aniston had helped to pair them up several months before the news was made public. "A few weeks ago things got a little more intimate between them," an insider told the magazine (via Digital Spy). "They are really bonding — they have more in common than anyone thought."

Of course, Bing — who died in 2020 at the age of just 55 — was no stranger to tabloid drama himself. Despite his insistence otherwise, it was eventually revealed that he'd fathered a child with tennis professional Lisa Bonder while she was still married to billionaire Kirk Kerkorian. His relationship with Liz Hurley also sparked countless headlines after he denied he was the father of the "Austin Powers" star's son Damian. His romance with Crow also proved to be short-lived, with Crow and Bing reportedly going their separate ways in 2008; neither publicly explained what happened between them.

After dating various high-profile musicians, actors, and sportsmen without much luck, Sheryl Crow appeared to change tactics in 2008 when she reportedly began stepping out with one of Alabama's most popular restaurateurs. John Cassimus had made his name taking over his family's Birmingham-based eatery, Zoe's Kitchen, before going on to launch Lounge and Maki Fresh, Jinsei Sushi Bar, and Marky's Kitchen.

According to reports, Crow and Cassimus enjoyed a brief romance in 2008 before the former's touring commitments came between them. "She's been so busy on the road all summer and with the baby," an insider told Us Weekly (via Today), referring to her shows with British singer-songwriter James Blunt and recently adopted son Wyatt. "Just no time for much else right now."

Unfortunately, for the nosier side of Crow's fan base, neither party has publicly spoken about their fling. In fact, shortly after being asked about the matter by AL.com later that year, the Grammy Award winner appeared to put the phone down on the interviewer.

It's been over a decade now since Sheryl Crow was last romantically linked to a famous man. The Grammy Award winner had been strictly platonic with Doyle Bramhall II — interestingly, a bandmate of her former beau Eric Clapton — for several years before she asked him to produce her 2010 soul-inspired eighth studio effort "100 Miles from Memphis." And it was here that sparks finally started to fly.

The pair showed up together at various swanky events including the Society of Memorial Sloan Kettering Cancer Center's Spring Ball and CMT Music Awards. But in an interview with Prevention Magazine, Crow decided not to refer to her new beau by name. "I've been involved with people and their kids, and if the relationship doesn't work out, it's heartbreak," she explained while discussing how Bramhall II had fit into her young family. "So I'm keeping the relationship friend-based when we're around the kids. Luckily, we have a great foundation, having known each other for 15 years."

Unfortunately, by the time that her follow-up record "Feels Like Home" hit the shelves in 2013, Crow appeared to be a single woman. She apparently remained on good terms with Bramhall II, however. Six years later, the pair were pictured beaming side-by-side at the Third Annual Love Rocks NYC Benefit Concert for God's Love We Deliver.