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Sheryl Crow Gets Real with AARP

In a candid personal interview, the singer talks about turning 60, her new documentary and fighting cancer and depression

Sheryl Crow with her guitar wearing headphones and sitting behind a microphone in a scene from the Showtime documentary Sheryl

Showtime

En español

It’s been nearly 30 years since Sheryl Crow, now 60, skyrocketed to global fame, and a new documentary streaming on Showtime charts her remarkable path to selling 50 million albums and earning nine Grammys while struggling with sexism, cancer and depression. In addition to the rock-star-filled doc, Crow has just released a companion 35-track double album, Sheryl: Music From the Feature Documentary, which includes three new songs in addition to her biggest hits: “If It Makes You Happy,” “Soak Up The Sun,” “All I Wanna Do,” “My Favorite Mistake,” “Everyday Is a Winding Road” and the James Bond theme “Tomorrow Never Dies.”

Weary of Los Angeles and media scrutiny, the Missouri native relocated to Nashville in 2003, adopted two boys, Wyatt and Levi, and is currently working on a musical and a one-woman show. Crow paused to share some personal reflections with AARP, talking about professional betrayals, sexual harassment and how much her relationship with her parents still matters to her.

Did you have any reservations about doing the documentary?

Initially, I said no. Documentaries are for when you’re done, and I still have a lot of creative life left. Even though I’m not commercially viable, I feel like a lot of my best work is happening now and is in front of me. And I didn’t want to do a retrospective of accomplishments. I wanted to do the story of the person behind the hits. 

What was it like to cover old ground?

It was draining. We did about three days of seven-hour interviews and then a couple of weeks later did three or four more days of interviewing. I’d struggle to remember everything, and revisiting some of it was very emotional. I was exhausted.

What did you learn about yourself in the process?

I was a fully realized person before I moved out to L.A. My first album didn’t come out until I was almost 30. I don’t think I lost myself, but I got really bogged down with the struggle of keeping myself grounded. It’s easy to do in L.A. You compound that with depression and all the things that are part of real life. It doesn’t line up with what fame looks like. Fame is a beautiful coat of paint. It’s hard to maintain that. It’s like the Golden Gate Bridge. As soon as you look perfect, it all starts cracking. You realize what matters is what’s on the inside and who you started out as.


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Your 1993 debut album, Tuesday Night Music Club, took a rough personal turn when some of your collaborators turned against you. What happened?

I felt like I went into it the way my parents raised me. You’re a nice person and work really hard, then everyone is cool with you. That’s not reality. I gave everyone equal publishing and hoped they would be happy. Nobody expected the album to be really huge. Once that happened, everyone wanted to be in that spotlight. Ultimately, the album was mine. It became bait for a lot of resentment. Some things happened that crushed me, and I didn’t handle it well. I internalized it and then personalized it.

Who gets you through your toughest times?

I’ve been lucky. I’ve had the same manager for 30 years. He’s a really good person. We’re like an old married couple now. It’s not like we go through life without disagreement, but he’s someone I’ve counted on and he’s never once told a lie to anyone I know. There’s something beautiful about having a manager who is looking out for the well-being of his artist over any monetary rewards. And I’ve leaned on my parents. I’ve gone through things that were really hard, like being sexually harassed, and I called my parents and said, “I don’t know what to do.” It’s rare you can turn to your parents and say, “I need someone to hear me.” 

You were brushed off when you sought legal help after Frank DiLeo (Michael Jackson’s manager) began sexually harassing you during your time with the “Bad” tour in the 1980s. Are you encouraged by changes since then?

With the #MeToo network, a complaint doesn’t go unheard, nor does the knee-jerk condemnation of the woman happen. It isn’t perfect, but at least women can speak their case and be heard and not be vilified.

Sheryl Crow at 2022 Billboard Women in Music Awards

Robyn Beck/AFP via Getty Images

Sheryl Crow at the Billboard Women in Music Awards at the YouTube Theatre at SoFi Stadium in Inglewood, California on March 2, 2022.

And are you seeing a better environment for women in the music industry?

For me, it’s an odd thing. I think, Have we come that far? I’m raising two boys. I can’t let them watch award shows. And I have to be careful about what they listen to. Women definitely are masters of their brands and owners of their personas. But the amount of sexual imagery out there — what is the message? Is it that we’re not strong enough to be intelligent, incredible artists and musicians? I don’t know where we’re at as female artists if so much of it relies on sexual image. I’m obviously an older artist, and I’m trying to make sense of it. 

Your romantic life was put under the media microscope, especially when you were engaged to Lance Armstrong [the couple split after his doping scandal]. How did you cope? 

Most of my relationships were public, and it was a challenging terrain. I’ve been really good through the years at ignoring my own press, but there was a point after Lance and I split and I got diagnosed with breast cancer that I couldn’t walk around my house because there were cameras shooting through the windows. I did feel at that point I needed to move closer to home. Nashville was a great option because it has a music industry, my sister lives there, and it was three hours from my family.

You’re private by nature, yet you went public with your cancer ordeal and became an activist. Why?

I was in such a state of shock when I got diagnosed. I put out a statement just to say I’ve been diagnosed and that one in seven women will be diagnosed and I’m going to meet this head-on, and I asked for privacy. I wasn’t sure I would ever speak about it again. Because it lifted me out of some toxic habits and toxic relationships and dictated that I refine my life and redefine who I was, I decided it might be worth talking about.

In the documentary, you also address your history with depression.

Having low lows is no joke, and it’s not to be taken lightly. Young people are committing suicide. We need to address this like any other health issue. We need to be able to talk about it. What [Olympic swimmer] Michael Phelps has done has been really beautiful. He and so many people have said, “I look like I have everything going for me, and yet I have this preexisting thing that is part of how I’m made, and I’m going to encourage other people with this to get help.”

What led you to adopt?

After I went through cancer treatment, I didn’t know if I’d go back to music. I had always wanted to have kids. My mom said, “Be a mom. Get a sperm donor. Get a surrogate.” I didn’t necessarily feel like I wanted to have a baby. I just wanted to be a mom. I started the adoption process, and before I knew it, I had two beautiful boys. I never let them be in social media, so putting them in the documentary is the first time I let them be seen.

Sheryl Crow plays the guitar onstage

Showtime

What’s their take on the rock ’n’ roll lifestyle?

They know it’s work. It’s not just having thousands of people sing along onstage. Most of what they have witnessed is the tour. They love it: bringing out guitars and helping the guys and getting paid $10 a show. Mostly, kids just want their moms to be moms. They want things to be normal. When I’ve asked them if they want me to retire, they say no, no, no. Until they say, “Let’s stay home,” we’re all going to load up like the Partridge Family and go. I don’t know if there’s an out-to-pasture buzzer that goes off. If there’s a clear signal that it’s time to stay home, I would have no reservations about it.

You turned 60 in February. How did you celebrate?

It was wonderful. My kids took me to a movie, and then we went to Panda Express. I don’t love the number because it reminds me that I should be like my grandmother. But I don’t feel that. I’m in the most rarefied position to be a musician and to have a youthful outlook and be inspired. It keeps me young and awake, and I have these two young boys who keep me jumping on the trampoline and playing basketball.

Was it a significant milestone?

There is something kind of beautiful and liberating about turning 60. I’m no longer competing with any of the 20- or 30-year-olds. I can write what I damn well please. I can do it just for myself or my children. I wrote a song called “Forever” for my children, and I hope they someday will want to sing it for their children. What our kids struggle with now is so different from what I struggled with. A couple of albums ago, we wrote a song called “Wouldn’t Want to Be Like You,” informed by people in high positions who lie enough that even they believe their own lies. There is a galvanized community out there that wants music that is truth-telling. That’s why I’ll keep doing it.

Edna Gundersen, a regular AARP music critic, was the longtime pop critic for USA Today.