Exclusive: Sheryl Crow Talks About How Michael Jackson and Don Henley Shaped Her Style

Introducing Endless Mode: A New Games & Anime Site from Paste

Read our announcement | See the 10 Best Games of 2025 (So Far)

It’s been 24 years since Sheryl Crow released her breakthrough debut, Tuesday Night Music Club, with hits like “All I Wanna Do” and “Strong Enough” vaulting her onto main stages almost overnight. But Crow’s career as a performer stretches back well before 1993, to her days fronting a college cover band, to stints singing backup for Michael Jackson, Don Henley and others. And it has outlived most of her contemporaries, thanks to her perseverance and ever-evolving songwriting and performing skills. With her new album, Be Myself, released last month, Crow is on the road yet again this summer, with stops this week in New York City followed by a slot on Willie Nelson’s traveling Outlaw Music Festival.

Crow spoke with Paste recently about growing into a consummate performer, from the lessons she learned when she was starting out to respecting your audience to her shifting sense of makes a great live show.

Paste: What do you consider to be your first significant live performance?

Crow: I took over for a girl singer, a lead singer of a band in college, and it was a really popular band. I had been the keyboard player and she quit and I got thrust into the frontperson role and that was the first time I’d ever seen myself as a frontperson. So here we are playing at the most popular bar in college and I’m filling in for the girl that everyone is used to. It was terrifying, but by the end of the night it was a blast. That, actually for me was a little bit of turning the corner, of getting out from behind my keyboard, where I was very comfortable. I didn’t really know what that was going to mean or where it was going to lead me.

Most Popular

“I feel bad for kids now who go on a TV show and immediately have 30 million people that are pre-ordering their record that isn’t even made and they haven’t had an opportunity to figure out who they are or who they want to be onstage.”

Paste: Could you see the writing on the wall even then?

Crow: Obviously in college, you’re not really even thinking that far in advance. At the time I was getting my degree in classical piano but I knew that I wanted to write songs and get my songs heard because I believed I was the right person to sing them. It took a while for it to become obvious because people started cutting my songs before I did and it was Don Henley that ultimately said, “Look, you’ve got to quit giving your songs away and you need to record them yourself.” At that moment I wasn’t thinking, “I’m going to springboard from this cover band into the world of being a recording artist-slash-rock star.” I just was following the course in front of me.

Paste: Did cutting your teeth in front of very small crowds teach you lessons you still employ on tour all these years later?

Crow: Absolutely. I feel bad for kids now who go on a TV show and immediately have 30 million people that are pre-ordering their record that isn’t even made and they haven’t had an opportunity to figure out who they are or who they want to be onstage. It takes a while to figure it out. It takes a lot of mistakes and I had the luxury of working out all the kinks without the annoyance of YouTube and cell phones and all that. Clearly, I’ve been around longer than social media has so I really got to hone my craft in front of small audiences. The audiences got bigger and I along the way got more professional and more clear about who I wanted to be and how I wanted to be and what I wanted to be. I got to do that in the shadows of touring and the exercise of playing live many nights in a row for many months.

Paste: Were there any standout shows early on that you now consider impactful to your career?

Crow: The big standout for me was in 1999, I believe it was. I played at Woodstock, the second one, and that changed the trajectory of my career overnight. The exposure of that and how people began to see me really shifted from that one gig. It put me on the map and from that moment on I was able to play much bigger places, and now you don’t really get those opportunities that often to really change things overnight without social media. You can do a lot of things on social media and millions of people can see it, but back then, there wasn’t that. It was word of mouth, and what happens with word of mouth is you create a really loyal fan base of people that were there way back when before anybody knew you and they discovered you and they told everybody else about you.

Watch a video of Sheryl Crow covering Guns ‘N Roses’ “Sweet Child of Mine” at Woodstock ‘99, an exclusive from the Paste Cloud.

Paste: Now that you are a seasoned stage vet, what are some tricks of the trade that have become indispensable?

Crow: I don’t know if it’s universally this way, but for me, my best shows and the ones I feel like resonate the most are the ones where I make eye contact with people. There was a few years in there where I’d been out for a long time and I was probably just overexhausted where I liked it when the lights were down and I didn’t have to see people’s faces. I find now that with people looking at their cell phones, you’re not making that connection that you used to make before there was something between you and the audience, and I really relish the opportunity to make a connection with people. That’s really what music is and has always been about, is changing the molecules.

Paste: You’ve been around the world several times. What are some of your favorite venues to play?

Crow: There are venues that are just mystical, like Red Rocks outside of Denver. It’s a mystical place. It’s an Indian burial ground out there and it’s right in the middle of this gigantic rocks and it’s a beautiful place and it’s been there clear back to the ‘20s or ‘30s. It’s been there a long time. That’s an amazing place, and the Gorge out by Seattle, where the backdrop behind the stage is miles and miles of almost what looks like the Grand Canyon. It’s gorgeous landscape. Then there are places that are historic. The Beacon [in New York] and the Troubadour [in Los Angeles]—places I love playing because you walk in and you feel that weight of what’s been there before.

Paste: You mentioned Don Henley as an inspiration early in your career. Who else have you learned from by touring with them and watching them night after night?

Crow: Before I ever got a record deal, I had the good fortune of touring with Michael Jackson as a backup singer. Then, after that, I toured with Don and it was really a very effective case study in different styles of touring. With Michael, that was a huge traveling circus of people. He didn’t really fraternize with the audience too much and every night’s show was always exactly the same… almost like a Broadway production. Then, touring with somebody like Don, he would spend all of his time with us and we laughed together and we would go eat dinner together and we would have that familial experience. I think that resonated more with me, but it was amazing to get to observe what makes all these artists who they are and why they’re effective and successful. It was such a great, and still is a great, thing to witness. Every time I go out onstage with somebody and I get to share the stage with somebody, from Levon Helm to Mick Jagger, I get to rub up against greatness.

“My first big hit was ‘All I Wanna Do,’ and I got really burned out on playing it on the first tour because the first tour was two-and-a-half years long. We decided to revamp it and I learned an invaluable lesson from that because I probably lost quite a few fans. We reworked it onstage to be like a Jack Kerouac beat version of it, and I think we left a lot of people leaving, scratching their heads, going, ‘Why didn’t she play the hits?’

Paste: Do you still get nervous before you take the stage, or while you’re onstage?

Crow: Yeah, I get nervous. I get nervous when I’m singing somebody else’s song and I’ve not really sung it before. I get nervous when there’s somebody in the audience that rightfully should make me nervous. I get nervous when it’s live TV and a new record, I’ve not performed the song that much and I’m worried I’ll screw up or forget the lyrics. For the most part after the count-in, you’re off and running and you don’t have the luxury of worrying. You just have to be in it.

Paste: You’ve had the gift and the curse of scoring hits that people have expected you to play again and again for many years. From a performer’s perspective, is there a burn-out factor on those songs, and is there anything that you do to keep them fresh for yourself?

Crow:”All I Wanna Do” is probably my biggest hit—that and “If It Makes You Happy,” and maybe “Every Day Is a Winding Road.” But really my first big hit was “All I Wanna Do,” and I got really burned out on playing it on the first tour because the first tour was two-and-a-half years long. We decided to revamp it and I learned an invaluable lesson from that because I probably lost quite a few fans. We reworked it onstage to be like a Jack Kerouac beat version of it, and I think we left a lot of people leaving, scratching their heads going, “Why didn’t she play the hits?” The reality is people have an experience that goes along with the song. It takes them back to where they were when they heard it or they relate it to a certain time in their life and they want to hear that version, and a little gratitude goes a long way. That’s the way I feel about playing the hits every night. I’m super grateful about the fact that “All I Wanna Do” took me around the world, from Tokyo to South America, and I play it and I try to play it pretty much exactly the way the record is because I know that that’s what people want to hear. I do have the luxury of having enough to play with that I can give songs a break for a bit. If I get really burned out and I want to drop one I can get away with it. I do try to that.

Paste: Looking ahead to the summer, you’ll be touring as part of Willie Nelson’s Outlaw Music Festival Tour. What kind of vibe and atmosphere should fans expect from this unique collection of artists?

Crow:I think that people are going to be transported by the fact that there are people up there still loving making music after 50 years, like Willie, and people who are still loving making music after 25 years, like me. Then there are people up there making music and loving it who are just getting started, technically, like Lukas Nelson the Promise of the Real and the Avett Brothers and Sturgill Simpson. They’re newer, they’ve acquired a lot of credibility and consistently are great, and you know they’re going to be around for a long time. I think it’s going to be one of those shows where you’re glad you were there.

Exclusive: Sheryl Crow Talks About How Michael Jackson and Don Henley Shaped Her Style

The singer looks back on the long road to becoming the performer she is today.