Sheryl Crow: A Musical Life with ‘My Best Work in Front of Me’

Sheryl Crow’s earliest musical memory begins in the backseat of a powder blue Plymouth Station Wagon. Only three years old at the time, she was being driven by her parents into the heart of her hometown’s commercial district when, fortuitously, Petula Clark’s “Downtown” came on the radio. Young Sheryl sang at the top of her lungs the whole way home.

It was the beginning of a lifetime of music that’s followed Crow from those simpler Kennett, Missouri origins to the height of musical superstardom in the 1990s, 2000s, and on through to today. When Crow speaks about those formative years now, it’s with affection for her hearth and kin, her parents’ musical tastes, and their encouragement for her to play piano for friends. But her favorite early singing memories of that time?

“It was really the quiet times when I could go sit at the piano by myself,” Crow says while stopping by the Den of Geek studio at SXSW. “I could play by ear, and I remember playing songs by Carole King and ‘Both Sides Now’ by Joni Mitchell, or James Taylor. That was soothing for me, being at the piano with the lights off and playing stuff by ear.”

This anecdote of first truly finding herself in her music, and in the dark, is also one of the early standout revelations in Sheryl, a new musical documentary slated to premiere on Showtime later this week. The film is a passion project from filmmaker Amy Scott, who along with her producer Brian Morrow previously put out the superb Hal Ashby documentary, Hal. Now with Sheryl, they’re able to similarly highlight the elusive qualities and quirks of fame, and what talent can both bring and take away from a life.

Not that it hasn’t given Crow a lot. In Sheryl, Crow can recall adolescent days of sitting in her childhood home and looking at the covers of her favorite records for Bob Dylan or Fleetwood Mac, and then later the doc cuts to Crow singing onstage, side-by-side, with Stevie Nicks.

“It’s a funny thing when you meet your heroes,” Crow muses now. “Because when I was coming up, there wasn’t social media, there weren’t all these different vehicles to really get a clear picture. What I thought of them, and who I thought they were, was partly my imagination through black and white photos and through their music and reading album notes. Then meeting them, because that was the generation of artists I loved so much, they did not disappoint. All of them, from Stevie to James, to Willie Nelson.”

She adds though, with a faint reflection on the ironies of life, that she could sing on stage with them yet still never quite be their peers.

Says Crow, “I always felt like, and I still feel like, I’ve been invited to the party but I’m the new kid, even though I’m 60 now. I’ll never get to be in that group, really, because I didn’t come up with them.”

Of course Crow’s cut her own formidable legacy through the music industry, as Sheryl meticulously documents. Once seen primarily as a unique So-Cal voice that married the sounds of country with alternative rock in the ‘90s, Crow wound up being a trailblazer in her industry, becoming one of the most popular and successful producers in an era when female artists were still pressured to be shaped by the male eyes around them; Crow also helped headline and lead Lilith Fair, the multi-million-dollar music festival spotlighting female artists from 1997 to 1999; and there’s that long string of hits: “All I Wanna Do,” “Strong Enough,” “If It Makes You Happy,” and “Soak Up the Sun,” among many others.

When asked about that impact Crow is modest, ambivalent even, but the filmmakers who’ve spent many months recently studying her career are hardly so undecided.

“You say it’s hard to look at your life objectively,” Morrow tells Crow while sitting in the DoG studio. “Well, I’ve looked at your life objectively for the past year, and you 100 percent had a gigantic effect on a lot of people. A lot.”

Indeed, Sheryl is almost a who’s who of music leaders, rock stars, and old celebrity friends who dropped by to offer their own memories of Crow through the years, and what the Los Angeles music scene was, then and now. Also according to the filmmakers, and unlike so many other documentarian experiences, the friendly answer of the participants was always the same: I’m doing this because it’s about Sheryl.

Says director Scott, “It was really fun, because the list of people [who agreed to appear] on the film… these are rock gods, musical heroes, and it’s just a testament to Sheryl. Usually you have to chase down interviews, and in this case, it was like, ‘Okay, let’s narrow it in and really tell a curated story here.’”

That story of this film began, really, when Crow first Zoom chatted with Scott during the height of the pandemic. Crow knew she wanted to tell her story as a doc and had discussed doing so with a number of filmmakers in the past—all women, she notes—but with Scott there was something in her style that seemed like kismet.

“She’s like a little rocker,” Crow says, “she’s edgy, and also she wanted to tell the kind of story that mattered for me.”

The heart of the documentary is a series of recent, in-depth interviews with Crow in which she and Scott candidly discuss Crow’s career, her aforementioned childhood, and the darker sides of the industry, including Crow’s own experiences with sexual harassment and the withering scrutiny of celebrity. They also are able to dive into the fun, unseen side of that lifestyle by revealing never before seen behind-the-scenes footage and home movies that Crow had accumulated over the years.

“We kept asking, we kept trying to get Sheryl to send us [material],” says Morrow. “Do you have any footage from that? Do you know anything around there?” Eventually Crow found a Tupperware box filled with what she called “the mother lode.” One hundred eleven VHS tapes spanning every era and many touchstones of her life.

“So there’s going to be a docuseries,” Crow cracks.

Yet even though there’s plenty they had on tape, one of the last quirks of fame from the late 20th century is there are still major events and life milestones that were never recorded. One of the most amusing anecdotes all three have to share is about Crow’s brush with the last gasp of old school Hollywood and the type of parties that could exist in the days before everything was on Instagram.

“It’s one of the more heartbreaking parts to cut out of the film,” says Morrow. “Sheryl’s got some great stories about these epic parties that she used to host during that time in her life, and the stories were just so funny, but it ended up having to come out because there’s no B-roll and there’s no archival at all. It was back in the day before everybody had a cellphone.” But that was what made them cool; there were no photographers or press. Not even the prospect of someone trying to live tweet it for publicity.

Says Crow, “I used to have epic, old school Hollywood parties. Like Jack Nicholson and Warren Beatty, and Marianne Faithfull, and Stevie and Gwyneth. It was such a fun time before all the social media, before cellphones that you could get together and people would just start turning up.”

She offers one such tantalizing anecdote: “I had a party for the Rolling Stones once, and John Travolta and Kelly Preston, who was a dear friend, were there and we projected on the side of the house Urban Cowboy, and John was watching it and going, ‘I love this movie. I think this is my favorite movie I ever did.’”

What is in the documentary are some of the more poignant and pointed connections in Crow’s life, celebrity or otherwise. For instance, a striking vignette is about the time Laura Dern became Crow’s roommate, watching her practice and rehearse, and as told from the vantage of Dern herself.

“I do feel like there are certain people in your life that you’re just familiar with,” Crow considers. “From the moment I met Laura, we’d always been really, really tight, and in a way that was more straight to the point at a soul level. And she’s been not only a rock, but also just the best kind of friend you can have… and there was a point where I did have her move in. I had a guest house, and we’re spending so much time together, and her relationship was falling apart, and my relationship had fallen apart, and I had the empty space.”

She adds, “In fact, we used to call that house the Home for Wayward People, because I had people living there before her who had also fallen out of relationships. So as I get older, I’m so grateful for her and for the women who are my tribe.”

Connections like that have become vital to Crow’s life as she navigated both the highs and lows of an industry that trades in artifice. Crow hopes she’s changed things a little for the better and is happy to see the #MeToo movement hopefully giving women a stronger voice, but she’s still quick to point out that when young women break through in the music or Hollywood scene, male journalists will still “first write about what she looks like before they write about her talent, and those little things chip away.”

To demonstrate that from her own experiences, Sheryl begins with a television interview from the ‘90s where the male journalist essentially asks if Crow is aware that she is called ‘driven’ as an insult. Crow does not think that’s changed today.

“I think unequivocally whenever you call a woman ambitious, it is a backhanded compliment,” Crow says. “It’s derogatory, whereas if you call a man ambitious, it’s a compliment, it’s to be praised. It doesn’t look good on a woman. We’ve seen it in politics, we see it when a woman runs for president. I mean, a woman should be President of the United States, but we’re not going to vote for a woman who seems ambitious and who’s willing to fight for her position.”

Looking back at her own career of navigating that world, Crow admits she’s had her own struggles with the artifice of celebrity too.

Says Crow, “I think the film shows that, right upfront, I wasn’t prepared for what [fame] was going to be like. There is no handbook for when you go on a talk show… there’s also no description of how you’re going to feel the night after a Grammys.” The nine-time Grammy winner goes on to offer an intriguing, if ambiguous, insight into what it’s actually like to be there on the night where ostensible peers compete for trophies and awards, all while being expected to smile and even sing along for the cameras in the Grammys’ case.

“You’re going to pretty much feel crappy,” Crow considers. “You’ve been in a room with so much energy, and that is not a loving energy. It’s full-on—I can’t even explain the weird energy that exists in a room full of celebrities. But if you’re someone who’s sensitive, you come away from it feeling like, ‘Ugh, I just need to take a shower!’”

Nevertheless, as Sheryl underscores, the musician feels better about her life and the way she lives it now. And she’s seen true hardships that are greater than any synthetic situation manufactured by celebrity.

“I don’t want to glorify my stint with breast cancer,” says Crow, “It was excruciating. And obviously it was detected very early, so while there was no fear that I was going to die of it, there was certainly a concern that it might come back. But that was the moment where I kind of looked at all of it and thought, ‘Okay, who was I originally? How do I get back to that?’ And you do at a certain point have to take a full picture. There’s a world of pain that goes into wanting to be an artist. I don’t know if the healthiest people wind up being the most successful artists. The most fully rounded stable people are not necessarily the ones who are going to write heartfelt music and put themselves out there.”

Yet the anxieties and, as one colleague says in the doc, “mind-fucks” of fame seem a lot clearer now than they used to.

Says Crow, “If you’re a person who takes that on, which is, ‘I want everyone to be happy with me, and at the same time I want to write really important music, not just good music, not just successful music—and wait a minute I’m 40 and now everybody on the radio is 17, and now I’m not getting played. Do people not like me anymore?!’ There’s nothing natural about the way it works, and yet it is what it is. I think having breast cancer made everything come to a screeching halt and allowed me to reassess what I wanted the second chapter to look like.”

Crow notes the industry has changed, but her aspirations have not. She says that her “still being around is a testament to not my drive but my yearning to still write great stuff, and to always feel like my best work is in front of me. I love the work. I want to keep getting better.”

And she can still light up a room, literally, as she did the night before our interview where she packed an intimate show at an Austin landmark for the Sheryl afterparty, getting a standing room crowd to sing along.

Thinking about that and her earliest musical memories, we ask if she still likes it best to play music in the dark. The singer-songwriter laughs.

“I like all the lights on!” Crow says, emphatically. “I joke about being radiated full tilt. My lighting guy out front [last night] was like, ‘Dude, we have to turn the lights out, you can’t have everybody [lit.].’ But I want to see everybody, I want to make that connection.”

Sheryl premieres on Showtime on Friday, May 6 at 9 pm.