Director Amy Scott delves into the extraordinary life and career of Sheryl Crow in new documentary

Sheryl Crow still vividly recalls hearing herself on the radio for the first time. “Now, I’m living in a studio apartment still. My manager is working out of his storage closet. I’m driving back from the dentist, in an old banged-up convertible past Rolls-Royces and Bentleys through these mansions,” Crow recounts. “I hear ‘Leaving Las Vegas’ on the radio and it was literally like a bad John Hughes moment where I’m screaming, ‘This is me on the radio,’ trying to get people’s attention. I can’t even explain how it felt. I wanted to pull my car over and jump up and down.” 

The nine-time Grammy winner may have stopped leaping for joy every time she hears her own music played, but having recently turned 60, Crow still feels extreme gratitude whenever a hit song of hers hits the airways. “It’s not an everyday thing to have a hit on the radio and become the soundtrack to people’s lives,” she says with deep appreciation.  

Realizing how rare a three-decade career trajectory like hers is, Crow also has no problem performing songs like “All I Wanna Do” at every concert she plays. “You have to remember when you’re up there the people whose shoulders you rode on, [the ones] who wrote the songs that you wanted to hear over and over. And you want to hear the songs you grew up to the way they sounded on the record,” she says. “I don’t look these gift horses in the mouth. I play them with total gratitude, and I make eye contact when I play them.” 

As Crow now enters her “legacy artist” phase, or as she says, “you’re old and you’re still around,” she is opening up about her life in a feature-length documentary, helmed by Hal director Amy Scott. Known mostly for her upbeat pop songs, the film is an opportunity to get to know Crow deeper, including her fights against sexism in a male-dominated industry, depression, perfectionism and breast cancer.  

SherylGracenote“I’ve always felt like documentaries were told after someone has already gone on after a fiery plane crash,” jokes Crow. “It was my manager, who’s been with me from the very, very beginning, that said, ‘Look, you have a powerful story. You have seen your business change. You have spent most of your life in the world of music and you have a story to tell. It’s time for you to tell that story.’” 

While the thought of opening up to Scott was initially hard for the singer, the hours of speaking about her life experiences made her realize there were stories of struggle within her journey that could resonate with others. “There are some experiences that obviously are not just my own in this business,” she says. “But to navigate running your career, running a business, for being a woman in what ostensibly is a business run by men—there is no handbook for that. There is no handbook for becoming famous when you’re a private, smalltown person. So, it was emotional.” 

Scott, for her part, went into the project with a somewhat superficial knowledge of the artist, based on articles and interviews available. It wasn’t until she sat with her completed interviews with Crow that she fully understood the story she was telling. “This woman dreams big dreams, gets a little bit up the mountain but gets knocked down, again. This was not an easy road to the top,” says Scott. “When you hear those songs in Whole Foods or Home Depot, it may seem so easy, but when you start to unpack the stories behind the songs—why they were written, what she was going through in her life—I was just blown away.”  

Songs like “Soak Up the Sun” and “All I Wanna Do” have painted a picture of Crow as happy-go-lucky, but with this project she’s ready to open the gates to a more complicated truth. “People have a very, very succinct opinion about who I am, which is largely because of the music that hit. I tell young artists all the time: Those songs are the gifts that give you the opportunity to write the stories about who you really are,” she says. “There’s pieces of me in every song that’s ever made it. But the deeper stuff, and the stuff that’s exemplary of who I am, are in the albums. This documentary is the first time that people who don’t know who I am will get an opportunity to at least have a better picture of it.”  

What it also might do is allow another budding artist to dream big. “Hopefully, some young person is going to watch this and go, ‘Wait. I’m in a small town. I don’t feel like I’ll ever get out of this place, and yet I have this gift that is pulling me out there,” says Crow. “Hopefully they’ll watch this and go, it’s possible.”

Sheryl debuts Friday, May 6th on Crave