“At Bonnaroo a couple of years ago, I was shocked at all the young people who were singing my old hits,” says Sheryl Crow, who adds, “I guess they’ve grown up with their parents playing them.” Crow, whose 33-year career includes more than 50 million album sales worldwide, thousands of concerts, and nine Grammy Awards, moved from Los Angeles to Nashville in 2005, where she lives on a farm with her two sons—Wyatt, 13, and Levi, 10. She continues to record in her home studio, and here, she talks with Lisa Robinson about longevity, women and the music business, motherhood, and romance.

Lisa Robinson: How do you feel about being called a “legend”?

Sheryl Crow: That’s a weird one. For a while I was considered a “legacy” artist, which means that I’ve been around long enough that I’m coming back in. But if I was coming up now in the business and had to deal with branding myself and using social media to promote myself, I would not be in this business. Obviously, I’m from a different generation, but I always liked the mystique: I was the girl who wanted to meet the guys standing in front of the airplane who had their packages showing in their jeans— Led Zeppelin.

I actually set up that photo taken by Bob Gruen at Teterboro Airport...

Well, I’m 58, and I love my age and my life. I had an interesting conversation recently with Robert Plant. We did a whole string of dates together, and I think he’s doing some of his best work; he’s doing what he loves, and he’s not rewriting his old stuff. He’s staying interested, but he’s frustrated because he can’t get any traction and can’t get his music played. But I said, ‘Doesn’t it feel good that you can still go out and do what you want?’ If you stick around long enough, you become a legacy artist whether you want it or not.

Well, he keeps turning down something like $300 million to do a Zeppelin reunion tour, but he always told me he didn’t want to go out and do “poodle rock.” And he called “Stairway to Heaven” “that wedding song.”

I’ll do it for $300 million [laughs]. No, nobody wants to see me sing Zeppelin songs— they want to see Robert Plant. But think of what you could do with that money to help your community...

Why did you leave Los Angeles in 2005? I remember you had an amazing house, and romantic relationships with, among others, Owen Wilson, Eric Clapton, and your engagement to Lance Armstrong.

I was diagnosed with breast cancer six days after my engagement fell apart, and I couldn’t leave my house because everyone wanted to get that picture of me at my lowest. It made me mad, not only at the paparazzi, but made me lose my faith in humanity. I was like, Who are these people who want to see this magazine, who want to see what I look like at my lowest? It’s one of the reasons I left L.A. I was just burned out. I didn’t have any roots. I was telling somebody the other day about a party I had for the Rolling Stones. Jack Nicholson and Heidi (“Hollywood Madam”) Fleiss were there—just a huge menagerie of people. Everyone more famous than the next. And in Nashville, I live on a piece of land that has five horses and 13 chickens, and I’m raising two boys. L.A. feels like it was seriously a past life. When I left, I was ready to leave. And for the last 15 years, I’ve just been making music in my barn and writing whatever the hell I want to write.

Did you see the 30 for 30 documentary on Lance this past year?

I saw a little bit of it, but I turned it off. It’s funny what time can do; I mean, it’s a part of my past, but it’s hard for me to relate to it. I just wish him well.

In retrospect, do you think that all the bad things that happened at that time wound up being the best things for you?

I’m a pretty spiritual person—I’m a huge meditator—and I find that all the big, traumatic events of your life can be digested in two ways: one with PTSD and the other would be the opportunity to remember who you are. When you’re a kid, you don’t have all these built-up traumas, and as you get older, you either get into patterns or you don’t. That time was a culmination of me looking at myself and thinking, You need to write the next chapter.

Did you ever have problems with drugs or alcohol?

I moved to Los Angeles when I was 29, and I lived a full life before I moved there. It was like Stevie Nicks—while she was cleaning houses, I was teaching school. My first record came out when I was 29, and I was already a fully formed person. And I’ve been outspoken about depression and how I’ve used alcohol to battle that. But I don’t have an addictive personality. If I did, I’d probably be dead by now. I can drink for two weeks straight and then never drink for six months.

You’ve talked about the sexual harassment you experienced from Michael Jackson’s manager Frank DiLeo when you were on the road doing backup vocals for Michael. Do you feel that the #MeToo movement has changed the music business in the way the movie business has supposedly changed because of all the allegations against Harvey Weinstein?

I don’t think there was anyone in the music business who could have been compared to Harvey Weinstein. Not that I know of. If nothing has changed, at least women are given permission to come forward and not have their careers be wrecked. I’d like to see things change more than they have. I see very few women promoters, very few women directors or female producers. I live in Nashville, where it’s a mark against you to be a woman. There are very few women engineers—I’d like to see that changed. Of course none of that compares to being raped by somebody.

Kacey Musgraves told me that she had problems with country radio because she wasn’t “nice enough” to certain radio programmers.

Money came in in the 1990s, and everything took a back seat to that—it wrecked everything. What’s happening in country radio is artists have to give free concerts for radio in the hopes of getting played on radio between three and four in the morning. It’s all about who’s going to be in the top 10 that week, and it works against women. All these people who sit behind desks and decide who’s going to be played—it’s all about the money. I had an interesting thing with my 13-year-old the other day—a song came on that I worked really hard for him not to hear, and when porn becomes the pop playlist...

Do you want to say what it was? Although I can probably guess...

No. But it’s all about money and who gets the most views or the most tweets. And women are fighting a losing battle. If it’s taking your clothes off in order to get a tiny bit of attention...I don’t think it helps our cause. It’s all about branding, and money. And this is why my 13-year-old, and other 13-year-olds, are going back and listening to classic rock—because they’re not stupid. Every song doesn’t have to be written for a six-second attention span. My kid is full-on into the Beatles, and I have nothing to do with it. At a certain point we’re all going to get sick of what we’re being fed by commerce. That documentary The Social Dilemma is so good—it’s no secret that what we see and what we’re gravitating to is all algorithms.

How can you run the farm, raise two boys, and still find time to make music?

I’m like every other working mom. You just do it, and you prioritize how to get it all in. Your kids are the priority, and then everything else is next. But I didn’t adopt my kids until I had already pretty much done everything I wanted to do. I had traveled all over the world. I sold 30 million albums. I was ready to have something else in my life that felt meaningful that wasn’t all about me. I did not feel that I missed anything by putting down roots and raising little boys; it’s been the top honor of my life. It’s bigger and cooler than anything else I’ve experienced.

How do you deal with them and social media?

This is the hard thing about parenting. My 13-year-old wants social media, and I won’t let him have it, and my 10-year-old wants to play tackle football, and when we get there, I’m going to strongly discourage it because I’m not about concussions. I’ve never posted pictures of my kids on social media—it’s not safe, and there’s no status in it for me. I think it’s gross, it’s narcissistic, and once they’re out there, they’ll always expect to have that notoriety. And life isn’t like that. My 13-year-old got a phone when he turned 13, and all his friends have Instagram and mine doesn’t, which is a source of frustration for him because he doesn’t want to be left out. When I was in seventh grade and left out of something, it was a bummer. But now you get left out of something and the pictures are everywhere and kids are talking about it on their phones. And it’s hard to be the bad guy mom—but I’m older and I see what it does. The one job I have right now is to raise these two people and guard their innocence. I’m not willing to trade that to be their best friend,

How did you all deal with the lockdown?

I feel guilty saying it, but [for me] it was idyllic, because I haven’t been off the road in 26 years or maybe longer—I started with Michael Jackson in 1987. And my kids never had a summer when they weren’t on a tour bus. So we basically had five months, and I [had to say to them], I’m sorry if you’re bored—most kids aren’t allowed to be bored anymore—but there’s a chicken coop and a creek and there’s a fishing pole. Go find something to do. I’m not a big ”go play Fortnite for three years.”

Do you miss being in a romantic relationship?

Sometimes I miss it. I would love to love. I’ve had amazing, loving relationships, and I miss being loved. But certainly my life isn’t on hold for that. At a certain age it becomes more about your happiness than having somebody complete you. Especially when you get to the age where sex isn’t the be-all and end-all. It would be nice to find somebody who makes you laugh and picks up after themselves.

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