Sheryl Crow on the Defining Songs and Favorite Mistakes of Her Career

“I used to cringe at the term legacy artist. But I feel like the gift of my age is embracing how long I’ve been around. Photo-Illustration: Vulture; Photo by Larry Hulst/Michael Ochs Archives/Getty Images

Sheryl Crow’s tweenage sons like to joke that their mom’s fame dates back to the Jurassic period. “It does feel like I’ve been doing this forever,” she says over the phone from her Nashville compound in early June. “But I’m like, ‘Wow, you don’t have to be so truthful.’” Well, more factually, she’s been around as long as the movie Jurassic Park. Her solo debut, Tuesday Night Music Club — technically, her second first album, since she scrapped her original debut — came out in 1993, the same year Dr. Hammond’s T. rex unexpectedly played hero. Also unexpected? Nearly 30 years later, both this former backup singer from Missouri and dinos born from amber are still very much rare gems.

Crow is not usually one for nostalgia, but the pandemic became a catalyst for revisiting her back catalogue. “It’s really the first time that I stopped working and had the luxury of knowing that nobody else was working either,” she says. For fun and, admittedly, “out of boredom,” she started playing songs she hadn’t gone back to in years. “There were a lot of revelations in going back and listening” to her 11 studio albums, she says. “Lines where I was like, Wow, I can’t believe I wrote that and now I understand why I did.” On June 18, she shared the stories behind her biggest hits and favorite deep cuts with the global livestream solo concert event “Sheryl Crow: The Songs & The Stories.” “It was really cathartic,” she says of the one-night-only show, which was filmed at her “little church,” a truly zen space on her Nashville property. “And not to sound hyper therapy-ized, but so much of the concert is a timeline documenting not only my growth as a person but the experiences that dictated me meeting myself. And isn’t that the human experience? We’re all works in progress.”

After almost three decades in the music business, Crow sounds as if she has reached a higher plane. Unfortunately, she hasn’t changed her mind about recording a follow-up to her self-declared final studio album, 2019’s Threads. “It almost feels like you’re writing a novel when most people are just reading tweets,” she says of making an LP nowadays. Instead, on August 13, she will release Sheryl Crow: Live at the Ryman and More. She’d also like to put together another storyteller’s livestream that includes the 18 songs she had to cut from the original.

For Crow, things have come full circle. The 59-year-old now inspires young artists like Phoebe Bridgers, HAIM, and Soccer Mommy the way Stevie Nicks, Linda Ronstadt, and Emmylou Harris inspired her. Without those legends, “I certainly wouldn’t be doing what I’m doing. I would actually just be a soccer mom,” she jokes. That passing of the torch has led her to think of getting older a bit differently. “I used to cringe at the term legacy artist,” she says. “But I feel like the gift of my age is embracing how long I’ve been around. There’s something really beautiful about having had this lengthy career and still doing what you love.” Now, let Crow share the stories behind her most personal album, her Lilith Fair duet with Prince, and how “If It Makes You Happy” ended up in a Britney Spears movie.

Standout Tuesday Night Music Club song

Almost every show we end with “I Shall Believe” and as I’ve gotten older and lived through some major life experiences — having cancer, adopting my kids, all the different changes in my industry — that song seems to hold more and more weight for me. One of the things that keeps me going is that I feel like I have not written my best song yet. There are songs that I am proud of, songs that really captured the moment of where I was at. But I understood [“I Shall Believe”] more later, and that’s what you hope. You hope you get out of your own way and allow inspiration to take over.

Sheryl Crow song you won’t skip on the radio

I can’t listen to myself. I mean, it’s terrible. I enjoy the moment of singing and I enjoy the moment of recording, but I don’t love listening back. I always feel like, Oh, if I was doing this live, it would be so much better. So it’s hard to take myself out of the equation and not listen with a critical ear. “My Favorite Mistake” is probably the one song where it comes on the radio and I enjoy listening to it. It’s the quintessential kind of perfect pop song, out of all the pop songs I’ve written, at least. I still really enjoy it. Other songs I’ve written don’t do that for me.

I enjoy playing “My Favorite Mistake” because I know that when I sing it I’m going to feel what I felt when I wrote it. Other songs you have to conjure authenticity, but that song takes me back to being with someone that I just loved and adored but knew that it was never going to be the forever relationship. I knew while I was in it that it wasn’t going to work out, but you love who you love. I feel like it’s one of those songs that everyone can relate to because who hasn’t loved someone that you know you’re not going to wind up with?

Significance of Prince ending up on stage with you at Lilith Fair

He had recorded “Everyday Is a Winding Road,” and we were in Toronto and he was in Minneapolis. He let me know through tour managers that he was going to be in town and would love to come out and play on “Winding Road.” For me, it was one of the most exciting happenings ever because you had all these great females on the side of the stage watching Prince come out and rule the day, as he does. It was really fun. A lot of it, too, felt like he was celebrating us women. He could have come out anywhere, but he came out on the Lilith, and it felt like, Okay, he’s here to support us.

Career-defining track

Well, every artist would attest to the fact that their hits were important, but more than anything they provide the opportunity to write the songs that really define you. “Redemption Day” is one of those songs that I feel is career-defining on a number of levels. It was important to me when I wrote it in 1996 about our involvement in Bosnia and our noninvolvement in Rwanda. Then when Johnny Cash recorded it [in 2010 for his posthumous album American VI: Ain’t No Grave], it was his statement for Iraq. And then, when it came out on 2019’s Threads, with Johnny and myself both singing it, it pertained to everything that’s happening now. If there were any song that I would want to be measured by at the end of my life, it would probably be that one.

The Johnny Cash moment on [the Threads version of] “Redemption Day” was also really a turning point for me. There was a moment where I was singing with him in my headphones and trying to find my way around him without taking away from him, feeling the weight of the song and eerily feeling his presence in the room with me. It was a moment where I felt like I could redirect my career in a way, where I could step back and say, Okay, this is my last artistic-statement-making album. From here on out, I’m going to write songs and put them out and have them be in the immediate.” That song was not only special to sing but also an epiphanic moment.

Best memory of the “If It Makes You Happy” scene in Britney Spears’s Crossroads

Usually, the ways those things happen — and I remember this to be the case for Crossroads — there are music supervisors on films, and they contact you and say, “Can we use this? We’ll pay you that.” I knew that they were going to have a scene where Britney and the girls were singing it and that it was an anthemic moment. Girl power, you know? And I loved that.

It was just funny because I can remember my 12-year-old niece wanting to see it and my sister not letting her go because it was about Britney Spears losing her virginity. I’m like, “Well, Aunt Sheryl isn’t going to be a completely conventional role model for you.” And I’m sorry, but the song was perfect for the moment.

Wildest rumor you’ve ever heard about yourself

Before I was well known, I was a backup singer for Michael Jackson. It was reported that I was being paid $3 million to have his baby. That was just straight-up bizarre. At that time, I wasn’t aware of how the promotional balloon works. In that particular instance, there were enough truths in that article, little things that were so inside, that I realized, Oh, this story was probably planted by somebody who worked for him to sort of conjure up rumors and to associate him with a woman. It was shocking.

Most personal album

I went into making [my third studio album] 1998’s The Globe Sessions having come out of a relationship that was not the forever relationship. It’s a very vulnerable record. I think at that point, I was also really meeting myself. It’s one thing when your first record blows up, and you’ve got a lot of people speculating about you. Then you make a second record that you feel like, Ok this should have been my first record because it’s very spot on. Then you come off of that and you’ve been all over the world and you’re kind of looking around going, Who am I? Who am I becoming? Where am I going in my life? There’s a lot of introspection on that record.

Song you’ve grown to love

I had a love-hate relationship with “All I Wanna Do” early on because it wasn’t one of my favorite songs. I look at that song now, and I play it with total gratitude because it took me all over the world. We played in South America, all over Asia, and in Russia, Vietnam, and Israel because of the notoriety of that song. I don’t look that gift horse in the mouth. Every time I play it, I feel an immense amount of gratitude. That song allowed me to write the songs that no one will ever hear.

Lyric that means more to you now than it did then

The first line of “River Wide” off The Globe Sessions: “I spent a year in the mouth of a whale.” The song was inspired by a poem from Walt Whitman’s Leaves of Grass, “Among the Multitude,” and the person I was involved with at that time had written the poem out for me. That was the last bit of correspondence I had with this person. When I think about [the lyric] “I spent a year in the mouth of a whale with a flame and a book of signs,” I think of the story of Jonah and the whale. He’s in the mouth of the whale, and he comes out alive, but his life doesn’t look the same anymore. It kind of dawned on me, looking back and singing this song for the livestream, that we do go through periods where we’re stuck in a moment. It may take time to realize the changes that happened, but as you get older, those moments that you’re stuck in and then come out of are the defining ones.

Your favorite mistake

Oh man, that’s a hard one. I feel like I’ve made a lot of mistakes but had to do it to get to know myself better. In the past, I’ve joked that I made two records before my first one came out. My first record never came out, and had I put that record out, I would have had a very different career — or no career at all. It was such a bland record, and instead, what wound up coming out was Tuesday Night Music Club, which was kind of radio defying. The fact that it didn’t sound like anything else, that it definitely wasn’t slick and perfect, was what made it stand out.

This interview has been edited and condensed for clarity.

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Sheryl Crow on Career-Defining Songs and Favorite Mistakes