Amy Scott on Capturing a Career in Music to Crow All About in “Sheryl”

Nineteen ninety-three was a big year for both Amy Scott and Sheryl Crow as the latter graduated from being a backup singer for Michael Jackson to being able to sell out major concert venues on her own on the back of the summer smash hit “All I Wanna Do” and the former was graduating from high school.

“Her music’s always been in the background of my young adult life, which when you’re going through your twenties and your thirties, all these moments are tied to some soundtrack somewhere, so she was always there,” Scott said of Crow, not possibly imagining then that their paths would eventually cross. “[But] a lot of things I just had no idea. I didn’t know about the Tuesday Night Music Club/Letterman drama, I didn’t know about the Michael Jackson of it all. I didn’t know about [Jackson’s tour manager] Frank DiLeo and the sexual harassment. There was a lot of stuff that was like, ‘Whoa, pretty fascinating.’”

As much as Crow’s willingness to bare her soul in her music has been a part of her enduring appeal, Scott learned the singer/songwriter left much unsaid during the making of “Sheryl,” a biography that like “Hal,” the director’s previous portrait of the late Hal Ashby, artfully sees the person beyond their creative genius. Opening with a clip of Steve Kroft pressing Crow to describe herself as “driven” on ”60 Minutes,” the film that follows allows the musician to pick her own words to chart a three-decade career that saw a young school teacher from Missouri finding more lucrative work recording a jingle for McDonald’s before a stint as a backup singer on Michael Jackson’s “Bad” tour put her in a position to meet her future manager Scooter Weintraub and producer Bill Bottrell on the road, leading to her breakthrough album “Tuesday Night Music Club.”

When inspiration for “All I Want to Do” came from an obscure collection of poetry (and its follow-up single “Leaving Las Vegas” from John O’Brien’s chronicle of alcoholism, which a gaffe about on “The Late Show with David Letterman” would lead to tragedy for its original author), Crow was bound to have a strange relationship with her massive mainstream success, dealing with the pressure to stay in the spotlight with one album immediately leading to the next and having a public image created by others at odds with how she felt privately. Crow, who shows an intriguing knack for questioning adjectives that others assume are positive, speaks candidly in the sanctuary she built for herself in Nashville, a recording studio that sits above a barn where she appears to be at peace and her thoughts can flow freely, whether for new music or reflecting on her life.

Acknowledging upfront “I’ve had a lot of high highs and low lows,” Crow adds new dimension to “Every Day is a Winding Road,” among many other tracks from her back catalog, and “Sheryl” inspires a new appreciation for how she found a way forward in her career on her terms. After the film’s triumphant premiere at SXSW, the film will reach the masses this week on Showtime and Scott spoke of the wild experience of having a pandemic partner in the iconic musician she hadn’t met before filming, the treasure trove of archival material that gives unexpected angles into Crow’s rise and how to think outside the box when getting someone’s essence on screen.

How did this come about?

During the pandemic, a producer at Gunpowder and Sky had gotten together with Sheryl’s manager because Gunpowder does these cool words and music [shows] like an audiobook, but it’s just different artists talking about their lives and careers, and Sheryl did one. It was really good and I think everybody was like, “Whoa, we’ve got a story on our hands that hasn’t been told visually and she’s ready to tell it.” They reached out to me and some other directors and Sheryl and I hit it off really well and this is like lockdown/pandemic time, so she’s actually the first person that I saw outside of my immediate family. [laughs] The first person I really spent time with was Sheryl Crow, so it was super surreal.

It’s such a hard thing to crack the biopic formula in an interesting way and you’ve done it twice – how did you figure out the structure for this?

I had a really good team. I have Brian Morrow, an incredible, incredible producer that works with me on story, and then my editor [Matt Thiesen]’s really brilliant too. But I think in and of itself, documentaries are in a really glorious renaissance right now and to be able to tell someone’s life in a film is really stressful and really hard to do because it’s templative, so you have to figure out where you can break form a little.There’s a lot of exciting filmmakers doing it. Morgan Neville is probably the gold standard for taking a person’s life and turning it in this way where it’s like “Here’s the moment that really defines this life, so we’ll spend some time here.”

For the Hal Ashby film, it was his films. Who he is and his values are in the movies, if we just mine the films. For Sheryl, it was hard because she’s had such a prolific career – all of us in our entire lifetimes will never have the amount of experiences that Sheryl’s had on a Tuesday afternoon, so it was hard to try and figure out where the story was and where to try and make it feel original and fresh.

One of the places you seem to find it is this idea of the metronome as a reflection of pressure. How did that make it in?

I cannot take credit for that. That’s my producer Brian, who’s like, “You know what we need? We need some kind of visual motif or language that will ramp up the anxiety” and if you’ve ever seen a metronome or let a metronome run, they run at different speeds and they give you great anxiety. It’s like, “Aghhh, make it stop.” So in those times where we [were] hearkening back to her childhood or time is passing and there’s going to be great anxiety, the metronome was always a really fun way to convey that.

There’s backstage footage in one of those sequences that I couldn’t believe. What was it like to get your hands on that?

This is another place where I got really lucky and I wrote this filmmaker Andrea Buchanan a letter and she came to the premiere. She was on tour with Sheryl for that whole “Soak Up the Sun” era and possibly more, but the tapes we got were Andrea’s raw archives. It was hours and hours and hours and there was one cut of the film where it was like, “I just want to live in the ‘90s on this mini DV fidelity tour world, it’s interesting enough for me.” And my producer’s like, “Let’s find the best moments.” [laughs] But we struck gold and felt like, somebody had the wherewithal, the knowledge to film this and to know that it was a historic time for a very historic artist who’s going to have this wild legacy career. But beyond that, she didn’t turn the camera off in really hard moments and that was the most impressive because most filmmakers would put the camera down, and go okay, “This is a little too much.” But the way that she shot it, she didn’t zoom in and it wasn’t voyeuristic. It was very cinema verite at its purest, so I was just so blown away and so grateful that she allowed us to incorporate her footage into our film.

You were saying earlier Hal Ashby’s films were his life and it’s obviously the same with Sheryl and her music. What was it like to figure out when to let the songs tell the story? As I understand it, a performance of “Weather Channel” was a breakthrough.

Definitely. It was very much in the same way that to learn about Hal, we just really turned his films inside out and really got in there, and with Sheryl, it was the same once I realized she wrote so many of these songs herself and produced them, so these songs were really her. She worked with incredible collaborators that were in the film, but at its core, it’s Sheryl, so [we dug into] those songs and she would telegraph it to us, like this is a hit and people love this song, but this other song over here is actually a little more accurate, so we’d pay attention.

When she played “Weather Channel,” I always thought it was a beautiful song, but for whatever reason I never really paid attention to the lyrics that much, at least with my mental health headphones on, so hearing it when she played it live in the church — and she was just messing around, it wasn’t like, “Sheryl, perform for us” — it’s just one of those things in life where the hair on the back of your neck stands up. I thought she was going to start crying and then we all kind of did afterwards and then it was something where I thought, “Ok, we need to talk about this. We need to get more into depression and what that means and what it means to be famous on the level that you’re famous, but yet not have X, Y and Z in your life.” It was pretty heavy.

What’s it like creating the environment that can happen in? Sheryl has said she felt protected by the fact that people were in the room crying with her in those kinds of moments, and your previous experience, it was about someone who had passed, so I imagine it was different. 

We’re a bunch of softies, and you don’t want to insert yourself in the process, but you want to let your subject know you’re empathizing with them and you’re in the moment, saying you’re right there with them as they’re moving through their story. With “Hal,” it was different because Hal wasn’t with us anymore, so we felt like private investigators for years, trying to find bits and pieces of him. The most emotional interview we had on “Hal” was with his daughter that he abandoned, so that was heavy and she’s now a really dear friend of mine, so you get in these places with people and they’re sharing their life with you and if you build trust and it all goes well, there’s just an alchemy in the room. With Sheryl, it was a luxury that she was willing to sit in that chair for as long as she did and take us through her life.

Was there any direction this took you may not have been expecting?

Oddly enough, I found the very first pitch treatment deck that I made to try and get the job and I read it to see, “Was I off the mark?” and it was relatively pretty close. [But besides] Andrea’s tour footage, but there’s so many little places in the film where we cut to these bits of VHS. Our crew thought Sheryl’s dad Wendell had a dedicated VCR for 30 years next to the TV and any time Sheryl came on the local news or whatever, he’d hit record, so we had those tapes. [Sheryl] sent us everything and had no idea what was in there. There was 16mm that had been transferred and she said, “These are my dad’s. They were in storage. 101 hours of archival footage.” And that came in at the 11th hour. We pretty much locked the cut and it was like, “Are you kidding me?!?!” [laughs] It really tanked Christmas, which was fine, but I was like, “Okay, we’re working in shifts” – my editor, producer and I – to get through it all. There were so many golden moments, so that was really, really special and we knew that was a gift and we had to give it the special attention. I keep telling everybody, I don’t know if we’re going to be this lucky every time, guys. There’s only one Sheryl Crow out there.

“Sheryl” will premiere on Showtime on May 6th at 9 pm and be available thereafter to stream on Showtime on Demand.