We’ve Got A File On You: Sheryl Crow

Dove Shore

We’ve Got A File On You: Sheryl Crow

Dove Shore

We’ve Got A File On You features interviews in which artists share the stories behind the extracurricular activities that dot their careers: acting gigs, guest appearances, random internet ephemera, etc.

In 2019, Sheryl Crow released what she figured would be her final album: the guest-stacked Threads. But as it turns out, Threads wouldn’t be her last project at all — in November of last year, the same day she was set to be inducted into the Rock And Roll Hall Of Fame, Crow announced Evolution.
Relative to her previous 11 albums, Evolution has Crow being a little more hands-off. The glut of her best-known work — beginning with 1996’s self-titled and 1998’s The Globe Sessions — has been entirely self-produced.

Evolution, which features already released singles such as “Alarm Clock” and a cover of Peter Gabriel’s “Digging In The Dirt” featuring Gabriel, is directly overseen by producer Mike Elizondo (Carrie Underwood, Fiona Apple, Mary J. Blige), who Crow sent demos to without even thinking that collection would become an album. And yet, here we are — Evolution is set to come out this Friday. 

A few weeks ahead of its release, Crow is Zooming in from her Nashville studio, which is appropriately lined with acoustic guitars. If those walls could talk, right? Crow acknowledges that, yes, she has seen a lot, but she’s taking most of it to the grave. “My manager’s like, ‘Man, you have got to write a book,'” Crow says with a grin. “And I’m like, ‘I should write a book, and then somebody can publish it when I’m dead, so that if anybody that gets mad at me, it’s too late. Sorry, Charlie.’ But yeah, I’ve got some stories.”

Below, Crow looks back on a remarkable career — one filled with odd jobs, big names, significant collaborations, and (more recently) endearing mom moments.

Evolution (2024)

You hadn’t exactly intended to make another record after Threads. That said, what were your main sources of inspiration for Evolution?

SHERYL CROW: My last record, which was called Threads, I said, “I’m never making another record.” 

I grew up loving records. I grew up pouring over album notes, and as my own producer, I always approach record-making, creating a whole sonic landscape at the beginning, a middle, end, blah, blah, blah. People don’t listen to records like that anymore.

This record came together because I was writing so much. It’s such a weird time to be alive. For me, particularly as an older mom, the only place I have felt like going to download what I’m experiencing and what I observe has been my back porch with my guitar and a cup of tea after school dropoff. I wound up having a bunch of songs and not wanting to go into the studio — just not wanting to do what I always do. I didn’t even want to hear me do me. I wanted to give this stuff to a friend of mine, Mike Elizondo, and have him make incredible sonic landscapes.

That’s what he did. I sent him these demos and said, “What do you think?” He’d take a day or two and build this incredible movie around it. It was the greatest gift. Before I knew it, there were eight or nine songs and we were like, “Gosh, it’s an album.” But I wasn’t thinking in those terms. I wasn’t writing songs going, “This is going to be for the next project.” After a few weeks of him tinkering around, I had a huge body of work. 

So by listening to someone else interpret your demos, that inadvertently inspired a new chapter.

CROW: Yes. The very first thing that he did was “Evolution.”

I sent him just the guitar and the vocal, which is what’s on here, and he’s like, “Give me a couple of days.” Then I went out and he played it for me. Well, first I started crying. I was like, “Oh my God, I feel like I’ve gone to the moon.” Then, part of me was like, “Oh, but I didn’t play the bass.” Well, he’s the greatest bass player that ever lived, so of course you didn’t play the bass, you idiot. So, there was part of me that was like, “Okay, I’m going to let go of the ego that goes along with being my own producer, of playing a lot of instruments and give myself this gift.” Once I let go of all that, it did feel like a gift. It felt like, “Okay, I’m taking myself out of the angst. I am just in the story, and I want to give these stories the greatest director that ever was.”

Next came “Broken Record.” Initially I called Mike and said, “I want to do ‘Digging In The Dirt’ because I’d done a guided mushroom journey.” I said, “I feel like this song just holds so much meaning for me.” He’s like, “I’m on board.” So, we did that and then sent it to Peter Gabriel, and he actually put himself on it. 

There were so many moments. I sent him a piano demo, this song “Don’t Walk Away,” which I felt like was so sad. Who would want to hear that? And he’s like, “Please, we have to do this.” So there just was never a “no” from Mike. There was never a “Not feeling this.” It was just, “Give me a day, give me a day.”

Running All-State Track In High School (Early ’80s)

Today, I get the sense that it’s much more typical for high school kids to be involved in multiple extracurricular activities, with sports overlapping with the arts. When you were a student, though, was it tricky to exist in multiple worlds? Did you ever feel like a rarity, being interested in music and also athletic?

CROW: Well, first and foremost, I grew up in a very, very small town where every kid went to the same junior high and every kid went to the same high school. I also grew up with musical parents, so I was absolutely going to continue to take piano because that was a given. I was going to be in the choir, and I was going to be in the band, but I was also an athlete. 

As we were getting older, I noticed that I was in a lot of different groups, but I was not the most popular. When my friends started drinking and smoking weed, I started getting left out. I mean, these are typical experiences. I even watch it with my 16-year-old — the fact that he gets invited to different parties with different groups. I told him at Halloween, I said, “That is such a testament to the fact that you like all kinds of people. If you stay out of all the texting between girls and bullying and all that stuff, it’s good to have a lot of friends because those people are the ones that ultimately you define yourself by.” 

So, for me, there were a lot of us kids that did everything mainly because of being in a small town.

Does your 16-year-old listen to you when you impart a little wisdom? Or is he just like, “Okay, mom.”

CROW: I think he probably acts like he’s listening to me, and then when I walk away, he’s probably rolling his eyes now. My 13-year-old rolls his eyes at me. My 16-year-old does it when I’m not around.

Singing In Cover Band Cashmere While Attending The University of Missouri (Mid-’80s)

In your earliest music gigs, how did you envision yourself as a performer? Did you picture yourself as a member of a band, a solo singer, a backup singer — or something else?

CROW: I never saw myself as a front person, not even for one day.

It’s funny thinking about high school, I always played for the musicals. I never was in the musicals. In bands I was always the keyboard player. In the cover band I was in, actually the next two cover bands I was in, I was the keyboard player. 

The last one that I was in, the front singer left to go be on Star Search. That’s how long ago it was. This is pre-The Voice, pre-American Idol. I stepped into her role, and it was the first time I’d ever been a front person. I wouldn’t say I was great, but I would say that being in a cover band was one of the greatest educations. I wish every kid could do it. When I moved to St. Louis, I got in a band. I was teaching school, I was singing in bands. 

I don’t know that I saw myself as being a front singer in a band, but more of a singer-songwriter. Because that’s what I’d grown up listening to. I grew up listening to James Taylor, Carole King. I grew up listening to Stevie Wonder, although he’s not a singer-songwriter, but certainly somebody who sits and writes their own songs. I saw that as what my journey was going to be.

Singing Jingles For McDonald’s And Toyota (Mid-’80s)

An artist being involved with advertising is also perceived so differently today. I get the sense that most working musicians and composers would be delighted to contribute to an ad. There are just so many fewer ways to make a living as an artist. The ‘80s and ‘90s, however, were less forgiving around merging the two spaces.

As a young artist, did you ever feel any sense of conflict around being in the advertising space? Or was it just a means to an end? Did you embrace it for what it could do for you in terms of financial stability?

CROW: When I was living in St. Louis, I was teaching school. I was in a band. A producer came in and asked me to sing on a commercial that ultimately did go nationally, and it was a McDonald’s commercial. It paid me in about 45 minutes of work, more than the two years of teaching. I wound up doing more of those, which afforded me the opportunity to go to LA. I took that tape around to all these different advertising agencies in hopes of being able to do some jingle singing. Then I wound up going on the road with Michael Jackson. 

I think what I was thinking of more than anything else was trying to work as a working musician. It’s funny though, it’s like what you said, when I first broke, no one would have been in a commercial. No one would have been the face of a commercial or would’ve been the voice for a commercial until Bob Dylan and Sting. I think Sting did a Jaguar commercial, and then Bob Dylan did a Victoria’s Secret [commercial]. Then, after that, it was like all bets were off. It was like, wait a minute. You got paid how much to be the face of that? And people started changing. 

Also, I think that was the beginning of the industry changing into a commerce-based industry where suddenly albums and cassettes went the way of digital. A cassette was $1.99, suddenly we have these CDs and they’re $15.99, and the record labels are making all the money. It was like a money grab, basically. Artists were like, “Wait a minute, we’re the ones doing the work, and you guys are all making the money.”

Now, we see it differently. Now we see it where the artists have figured out this influencing thing where you build up your persona, and then whatever you do with that — whether it’s “I’m going to write songs” or “I’m going to become a famous reality show person.” We’re seeing that individuals hold the cards and everybody else is trying to get in on that. I find it to be a very weird time. I am trying to still, I guess, rationalize what’s the quality of music and art if the brand is so much bigger. 

Then, compound that with “What’s the longevity of an artist if your persona is built around this brand that you’ve built?” You are going to get older. You are going to get wrinkles. You are going to age out, just like me. I’ve been blessed to have been around when all of that hadn’t started yet, so I’ve gotten to have 35 years. But I wonder, especially the pressures that are on women now to make sure you have the perfect lips and the perfect boobs and your skin is perfect. I wonder, what’s that going to look like? And what are we saying to not only young women, but young artists across the board? 

Doing A TikTok Susi Stitch (2024)

@sherylcrow My Grammy nightmare… I’m still traumatized. #susistitch #fyp #grammys #pianofail ♬ original sound – Sheryl Crow

Well, on that note, I really enjoy your TikTok feed.

CROW: My TicTac?

Yep. It’s great.

CROW: My kids were like, “You cannot be on TikTok, Mom. You just can’t. You’re too old. That’s so cringey.” They kind of like it now.

I noticed that since your music, on UMG, has been removed, you’ve been taking requests and playing classic songs live on acoustic guitar.

CROW: The recorded versions? Oh, not on TikTok. That’s right. [Points across the room] Actually, Liz, who’s sitting right there, does my TikTok. I’m like, “Is it not available on TicTac?” Yes. I think I did hear that about Universal. 
Honestly, with TikTok, I mean, that’s what I do. It’s sort of fun to be able to just sit and play songs. I don’t feel like I’m out of my comfort zone by doing that.

You even did a Susi Stitch!

CROW: Actually, that was really fun. I had that crazy Grammy experience, but I’ve had so many crazy experiences. I could step into Susi Stitch’s whole routine and have about 25 crazy [stories]. But some of the people [involved] would have to die first before I incriminated them, so I probably won’t.

But yeah, some of it is fun. Some of it is an opportunity to let people see that you’re a real person, that you’re not just a serious tormented artist who anguishes over … It’s funny. I remember we did an Instagram thing around The Murdaugh Murders because I was obsessed. I needed to detox from those. The response to it, when I was in the kitchen cooking, it’s like, do people not realize that you’re a person that has a personality, a real life? That you actually do load and empty your own dishwasher, and you do fold your kids’ underwear? 

Sometimes it’s fun to let people in.

Playing An Undercover Cop In Cop Rock (1990)

Let’s talk a little more about some early gigs. How in the world did you end up in a police procedural that was also a musical? It’s like a fever dream.

CROW: You know what is so funny about it? I feel like I had this life that I look at from an outsider [perspective] and just go, what? I mean, I used to have parties at my house where like Jack Nicholson and Warren Beatty [attended], and now I’m here in the school dropoff lane. 

But yes, I was on, I can’t remember, what was the name of that show?

Cop Rock.

CROW: Cop Rock. It was [created by] Steven Bochco. 

I’ll tell you how I wound up on the show. Steven Bochco was doing this series, and I believe he already knew that it was going to be canceled. But I met him through friends, and he asked me if I’d want to be on it. And I was just like, “Sure.” [I was] not really an actress, [and I] never made a school play, and I wound up doing it. When I watched my documentary [2022’s Sheryl], the one time I’ve watched it, I saw the footage — I am just in shock that I wound up doing it. Donna De Lory, who was Madonna’s backup singer, was on the episode that I was on.

I mean, I’ve had some crazy jobs. I’ve waited tables, I’ve waited on very famous people. I gave my cassette to Sting. I met Stevie Wonder in a club, and I just had a whole other life before even making it. I tell you what, in Cop Rock, you could see why I didn’t have the acting career that I really feel like I could have had.

Singing Backup For Michael Jackson, Belinda Carlisle, & Kenny Loggins (Late ’80s-Early ’90s)

I know that you’ve talked a lot about your time with Michael Jackson, but I wanted to ask you about the other performers, like Kenny Loggins and Belinda Carlisle, you did backup for. What’s an experience singing backup that you haven’t talked as much about?

CROW: It’s interesting. I sang backup for Don Henley, went on the road with him, sang on a session for Warren Zevon, sang on a session for Rod Stewart and Ernest Isley. I sang on a session for Nancy Wilson, who’s a jazz singer. I think there were 30 of us in the room. I was still very new in LA. We walked in and she met each one of us. Then, as we left, she said, “Thank you for coming, Sheryl.” She called each one of us by our names.

There are little things along the way, people that I’ve met — Johnny Mathis, David Foster — that you just go, “How did I get here? How did I get this opportunity?” I definitely think about it now as I’m older. I look at things so philosophically; certain things happen in your life that you could never predicted, and how does one person get so lucky. To be in an audience as a young schoolteacher watching Keith Richards on stage with Chuck Berry and Steve Jordan. Then, 30 years later, wind up in the studio with Steve Jordan and Keith Richards. 

I think one of the things that I don’t get to talk about is what I’ve witnessed in certain people along the way and why they were who they were. Spending the amount of time that I did with Prince in his domain and witnessing otherworldly brilliance, not schooled or, “Gee, he’s worked really hard and practiced his whole life” — an otherworldly [brilliance]. He got dumped onto the planet through somebody’s womb with all of this already in him. There are people like that. 

And there are other people where their egos are so big and they’re so intellectual that they’ve manifested this thing. You see it as you work with people. You feel the molecules in the room change when a Sting walks in or when a Bruce Springsteen walks in. There’s certain things that you go, “I can apply this,” but there are other things you go, “I can’t apply that. That is an aura and a divine thing.” What was in Michael Jackson, the mixing of ego and wounding and brokenness with divinity was, if you could see it at the same time, mind-expanding. 

Including “Hundreds Of Tears” On The Point Break Soundtrack (1991)

Your first studio album was scrapped because you felt it was too produced and ultimately not representative of your authentic sound. And yet “Hundreds Of Tears” makes it onto the Point Break soundtrack?

CROW: Actually, a lot of those songs wound up being covered by other artists. One of them went over to Wynona Judd, one of them got covered by Celine Dion, one of them got covered by Tina Turner. 

Well, this is what happened. I had a cassette that I had made from what was at that time, like Pro Tools. It was called Performer Program. It was very slick and very quantized, and it felt very much like a Sting record, right? That’s the way I made it because I worked with somebody. I wanted to make a record that felt more raw. 
I handed the cassette at a party to a producer that was very well known, who had produced Sting, and he loved it. We went in, he brought me to A&M. We went in and made the record, but the record I always felt like was too slick. Not only did I not have the stature, I didn’t even have the vocabulary for how to explain what I wanted while working with somebody who was much bigger than I was. 

When it was all mixed, I went into the record label and I said, “I don’t really even know how to perform this because it feels like it’s so slick and so commercial that I’m just going to botch it up and nobody’s ever going to …” So, they held the record, and they didn’t put it out. They let me have a second chance. That was a shaky start.
In my early days, I think because I didn’t have the courage to say, “This isn’t who I feel like I am, but I’m not sure,” I did a lot of stuff backwards. I’d make a record that was not what I felt like it should be in order to figure out: “Oh yeah, this is who I am.” That was how I got my sea legs. 

By the time the second record rolled around, where I had to compete with the nine million-selling record, Tuesday Night Music Club, I walked in and was like, “Okay, give me the steering wheel. I know what I’m doing.” But sometimes you learn the way you learn.

Crowded House’s Neil Finn Providing Backing Vocals For “Every Day Is A Winding Road” (1996)

When I was a kid, one of my favorite songs to listen to on the radio was “Every Day Is A Winding Road.” Of course, at the time, I did not realize that there’s a Crowded House backstory to that song, and that Neil Finn was on backing vocals. I’d love to know how that ended up happening — I saw that Paul Hester was an inspiration for the song. What is the story there?

CROW: Well, there are so many. I called my last album Threads. There’s so many threads in every single story and [they] weave all the way through my career.

One of them is one of the first tours that we ever got to be on when we first started hitting was Crowded House. It was monumental for us. We were huge fans. We were just starting to have success with “Leaving Las Vegas.” After the fourth date, Paul announced that he was going to be leaving to go home because he was really struggling. 

What wound up happening from that is that Crowded House asked to borrow my drummer for a few songs — just a few songs for a couple of gigs til they got somebody out. We wound up sharing my drummer the entire tour, and it was like one big family, which is not typical of the opening act. The opening act generally doesn’t get to see the headliner. But we were like a traveling circus, and it really threw all of us together, and it was such an amazing experience. I still have lifelong friends with Neil and the whole band. 

When I went in to make this record, I was working with Tchad Blake, who had worked with Crowded House. In fact, I believe one of the ways I wound up working with him was through Mitchell Froom, who also worked for Crowded House. I was going through, “Okay, I am making a record. I’m following up a giant successful record.” There are lots of little references to Paul and the fact that he named his daughter “Sunday,” which I thought was such an interesting name…

So, I wrote a song. I didn’t feel like it was the best song I’d ever written. When Chad heard it, he said the line, “I feel like I’m a stranger in my own life.” He’s like, “The whole album for me rests on that one line. You have to put it on the record.” Neil came in and sang on it, and it’s been one of those songs that has been a life buoy for me because it has recreated itself all the way through my career. Even during COVID, it meant so much to so many people when I would play it. It is one of those weird mantras that life is a winding road. Eventually you feel fine, but you have to keep working at feeling fine.

Almost (?) Joining Fleetwood Mac (2008)

There was some confusion in the late 2000s around whether or not you might be joining Fleetwood Mac, potentially to replace Christine McVie. Was that possibility ever actually on the table? Had you all jammed, or anything?

CROW: I had played on something for them. And of course, I knew Stevie [Nicks] very well. She’s my fairy godmother, so to speak, in so many ways. Dialogue started happening, and there was communication between managers, and I was very interested. But I also had two young babies, a 3-year-old and a six-month-old. I just had a baby. I don’t even think Levi was here yet. 

So anyway, the dialogue was happening, and there were other people that knew so it came up. And they were serious talks. When somebody asked me about what was happening, what was coming up next for me, I think I mentioned “We’re in talks.” And I know Lindsey [Buckingham] was very offended that I would say that before everything was finalized. So, the kibosh got put on it.

Honestly, Christine did come back, and that tour was amazing that she came back for. I could never have filled her shoes to begin with. But yeah, that’s kinda how that went down. 

HAIM & Lorde Covering “Strong Enough” (2013)

A lot of your biggest songs get some really great covers — one of my favorites is HAIM and Lorde covering “Strong Enough” in 2013. Is there an older cut of yours that you would love to see covered more by contemporary pop performers? Or an unheralded song that you’d love to give more shine yourself on tour?

CROW: I had a song called “The Difficult Kind” that was on The Globe Sessions. I’ve always thought, man, some great country singer could kill that song. 

Evolution is out now via The Valory Music Co.

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