‘Sheryl’ Director Amy Scott Discusses Her New Documentary On Rock N’ Roll Badass Sheryl Crow

Over the course of her 35 year career, Sheryl Crow has sold over 50 million albums worldwide, written countless hit songs and collaborated with some of the biggest names in rock, usually at their request. Unfortunately, she’s had to fight for respect each step of the way, with people more concerned with her celebrity than her artistry. The new Showtime documentary Sheryl , which premieres May 6, aims to correct that, successfully arguing for her artistic importance while also examining the personal struggles that have affected her life and music. 

Sheryl is the second film directed by documentarian Amy Scott. With a background in music and film editing, Scott earned accolades and award nominations for 2018’s Hal, which profiled groundbreaking ‘70s filmmaker Hal Ashby and was named one of that year’s top documentaries by Rolling Stone magazine. Scott spoke with Decider about the making of Sheryl, the challenges of documentary filmmaking, sexism in the arts, and what a badass Sheryl Crow is. 

DECIDER: How did you get involved in this project?

AMY SCOTT: It was the middle of the pandemic. Nobody was seeing anyone except for who you were podding up with. I got a call from Jude Harris at Gunpowder & Sky and they asked if I liked Sheryl Crow. I wasn’t a super fan but I was familiar with her work and they were like, “You might want to think about if you would want to make a film about her.” We didn’t have another conversation for four or five months but I wrote back and said I would be interested. 

There were a few other directors and we were all in various locations Zooming with Sheryl to get a feel for whether or not it would be a sympatico union. I think Sheryl and I kind of bonded. There’s a lot of similarities in our story. We both grew up in small towns. I told her the story I wanted to tell and she was really down. After that, she stepped out of the way. She didn’t dictate the story, she didn’t dictate what songs were going in. It was really a dream scenario. 

When did Sheryl see the final edit and what was her input?    

I worked really close with her manager, Stephen ‘Scooter’ Weintraub. I think if I’m being truly honest, I think he was the one ultimately responsible for getting me involved in the project. He also did not dictate anything but I shared different cuts with him. Since Scooter’s known Sheryl for 30-something years and is sort of the Sheryl-whisperer, we relied on him for when we should bring her in and show her because it’s a very, very, very delicate process. You can do it too soon and completely freak your subject out or you can do it too late, where you don’t have time to make the changes that they want. It was really stressful because she was going above and beyond and I was terrified of disappointing her. She was digging up things in storage and making road trips to find photographs. Fortunately, she was really excited about the film. I think it’s a hard thing for anyone. It’s got to be a psychedelic experience to watch someone else’s painting of your life and all of your failures and successes and vulnerabilities.         

One of the things that comes across in Sheryl is how many personal and professional ups and downs she’s been through. How did you choose what to focus on?

My producer, Brian Morrow, is my right hand, as well as my editor, Matt Thiesen. At every turn we were constantly weighing what the biggest story was and what the B-stories were. Because she’s still alive and has had such a prolific career, it was like, OK, it’s not just about the sexism, it’s not just about the depression or the celebrity, but they all contribute to this really marbled person that is Sheryl Crow. We had several different versions of this film, where the depression was the key, or where Sheryl’s biggest enemy was Sheryl, but it didn’t feel true. Part of that’s true, but that’s not the whole story. It was kind of constantly wrestling this snake on its tail. 

It’s interesting, because although the film isn’t solely about sexism in the music industry, it touches so many facets of her career, from actual sexual harrasment to how, in my opinion, she’s not taken as seriously as her male colleagues.

This was kind of a thesis of ours, too. I think because I was approaching it as more of an outsider and not a super fan – which I think is really good, if you’re going to make a film about somebody, you shouldn’t be a super fan – I came to the same conclusion as you. I think when a woman has that long of a career, and they’re that popular in the pop world, and crosses  genres, I think they lose street cred or something. But she’s as talented as anyone. She’s always been in this commercial space, I think to her detriment. In terms of record sales it’s probably great but she’s been under-appreciated in that way. That was one of the big things that I wanted to do, I wanted people to see how badass she is. Seeing her play when we were filming and witnessing the sheer musicality, that she could pick up the bass, switch over to acoustic guitar, jump over to a baby grand piano, she can play so many different instruments really well. It’s an elite athlete level of musicianship. 

Do you think being a woman gives you an advantage in telling women’s stories?     

I think it’s a good question and one we’re constantly struggling with, like, can you only tell the stories that you have a personal connection with, where it’s your story too? And I don’t think that’s true. That said, my producer Brian and I were constantly reviewing these clips and we could have done a super cut of all these late night talk show hosts being like, “…and the beautiful Sheryl Crow…the gorgeous Sheryl Crow…the stunning super hot babe…” It was never, “Here comes the talented songwriter…” or any of the other adjectives you could put before her name. I’m not Sheryl Crow-level anything in my life but in terms of being a female director trying to make my way in the film industry or just being a waitress, I’ve experienced these things. When you see it, it hits this place in your gut that’s very familiar, like a piece of wood on the floor that’s still creaky after 45 years. So, it’s easy for me to tap into all those places and then to see a clip and be able to go, “Oh my God, that was so sexist,” whereas it might not be as obvious to someone else.

The recent Tina Turner and Go-Go’s documentaries helped make the case for their induction into the Rock and Roll Hall of Fame. Sheryl Crow is both eligible and deserving, was this ever in the back of your mind while you were making the film?

It hadn’t occurred to me until we interviewed Jason Isbell. He was pissed and spent a significant part of his interview talking about how if she didn’t get inducted into the Rock and Roll Hall of Fame he was going to go burn it down (laughter). He had to walk it back and said, “I’m not advocating for violence, that’s not what I mean,” but as an institution, if they don’t recognize this woman, like, come on. She’s done so much. So I did think, “Wow, that’s so cool. He’s right.” She absolutely should be in there. Which goes back to our earlier conversation, about her being recognized as the badass rock n’ roll songwriter that she is.       

Benjamin H. Smith is a New York based writer, producer and musician. Follow him on Twitter: @BHSmithNYC.