Sheryl Crow on being 'hot' at 60 and why she's 'grateful' she never got married

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Ahead of the release of her documentary, Sheryl, music legend Sheryl Crow is opening up.

The singer stopped by The Howard Stern Show on Wednesday where she reflected on her love life, her legacy in music and why — at 60 years old — she has yet to marry.

NEW YORK, NEW YORK - MAY 04: Sheryl Crow visits SiriusXM's 'The Howard Stern Show' on May 04, 2022 in New York City. (Photo by Cindy Ord/Getty Images for SiriusXM)
Sheryl Crow is opening up about the ups and downs of her personal life, and why she never got married. (Photo by Cindy Ord/Getty Images for SiriusXM)

"I'm hot. Even at 60, I'm hot, right?" she told Stern. "Honestly, I even scratch my head and go, 'How did I get here without getting married?' ... I almost did, three times."

One of those men was cyclist Lance Armstrong, with whom she got engaged in 2005 before calling it off in 2006 — around the time Armstrong fell into controversy surrounding his highly publicized doping scandal.

"Everyone eventually grows up, figures out who they are," she said of the men in her life. "I give people a lot of leeway when they evolve."

Looking back, though, Crow doesn't regret her choices.

"I go, 'Thank you God. Thank you. I didn't get married,'" she said. "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."

The musician also touched on whether or not she feels snubbed by the industry given that she's yet to be nominated to the Rock & Roll Hall of Fame.

"I feel like I was always kind of an outsider and [by] having songs like 'All I Wanna Do' and 'Soak Up the Sun' define me, so many people wrote me off," she said, explaining that those feelings became the driving force on why she wanted to work with director Amy Scott on Sheryl.

"When they came to me and said do you want to do a documentary, I said only if the story of the person is told and not the rehash of the awards and … all that stuff," she said. "I was 30 before my first record came out, and I had real jobs — I was a schoolteacher, I waited tables for years and years. There is a whole life there that isn't just 'All I Wanna Do' and happy songs."

Furthermore, when reflecting on her life on the road, the singer spoke about being sexually harassed by Michael Jackson’s then-manager, Frank DiLeo. "I was pretty disappointed. You work hard, you're a nice person, put one foot in front of the other," she said. "I thought good things would happen."

Add that to the tabloid-driven rumors that she was being paid "$2 million" to have Michael Jackson's baby, which she looks back on and laughs now, Crow found herself in an uncomfortable situation.

"There's a whole backstory to that with having [Jackson's] manager take that notoriety that I was accruing and, you know, trying to architect some pop career around me and I didn't want to be a pop star," she said of that time. "And then the sexual harassment was involved in all of that and then the threat of 'You're never going to work' and my going home and putting bands together and playing my music and having everybody in the industry say, 'Well, we don't know what to do with the blue-eyed soul singer.'"

When that tour was over, Crow said she ran out of money and had to take up waitressing again.

"It was tough, it was really tough," she said. "I mean, it's tough coming off the road and just sinking back into your own life no matter what, but that was some other kind of tough."

Still, despite the ups and downs in her personal life, Crow remains optimistic about the future — especially when it comes to love.

"I like funny people," she said. "I've dated famous people, I've dated athletes, I've dated not-famous people," she said. "It's an open opportunity for anyone to be in the category of my next 'favorite mistake.'"

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