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Interview: Bill Simmons and the Creators of HBO’s ‘Music Box’ Series Discuss the Windows of a Musician’s Career

Famed journalist and sports analyst Bill Simmons put a fresh spin on music documentaries last year with the release of season one of Music Box on HBO Max. The series features six documentaries, each by a different filmmaker, each showcasing a different artist. We got the chance to listen in to an HBO FYC panel event with Simmons and all six filmmakers to discuss their projects.

If you’re a fan of music documentaries, you might be aware that they have a typical structure that Simmons points out:

“[Music documentaries] tended to be very beginning, middle, and end, look at somebody’s whole career…As we started to shape it, we’re thinking about how do you concentrate on windows, or parts of somebody’s career, or the piece that’s usually the best part of the documentary.”

The next mission was to find filmmakers, “trying to find voices that we liked, people that we potentially wanted to work with and then trying to marry ideas.” Simmons remarks, “I think we accomplished it. I think if you look at the six together, they all make sense, weirdly, as a group, even though the subjects that we picked do not make sense as a group.”

The first film in the lineup, Woodstock 99: Peace, Love, and Rage chronicled the infamous 3-day festival that quickly fell prey to oppressive heat, violence, and vandalism. Director Garrett Price explains his intention to portray the event the way attendees must have experienced it:

“Woodstock 99 played out like a slasher film, that’s what really excited me. It’s a bunch of teenagers going to the woods for a weekend of sex, drugs, and rock and roll and horrific things start to unfold as that weekend progressed…You know, this bunch of kids going to this festival. And it gets darker and darker on that weekend, it was getting darker and darker in that edit bay as we started making this film too. I wanted people to experience what I was experiencing as I was telling this story.”

The next film, Jagged, follows Alanis Morissette, zooming in on the release of her 1995 album Jagged Little Pill. Director and longtime Morissette fan Alison Klayman talks about her decision to center this moment in time:

Jagged Little Pill was the first album that I bought on CD and I listened to it over and over, studied the liner notes, it meant so much to me as a young kid. I felt that a film that focused on that album’s impact, both taking the phenomenon it was and what it looks like 25 years later…I was really excited to do it and I felt like we got to do something that was personal about the artist but also about an album that meant so much to millions of people.”

The third film, DMX: Don’t Try to Understand, chronicles a year in the life of rapper Earl “DMX” Simmons just as he’s released from prison in early 2019. Director Christopher Frierson discusses his memories of seeing DMX in the news as a kid:

“I saw how he was portrayed in the media as dealing with addiction, and with the police, and getting arrested, and I thought his narrative was not one of his own. It was very TMZ-ish and very exploitative and you could hear the pain behind it,” recalls Frierson. “I thought his story needed to be told.”

When asked how he was able to get so much access to the rapper’s story and inner life, Frierson explained that as a friend of DMX’s manager, he was present on the day DMX was released from prison: “In the movie, he gets in the car, and that’s the first time I met him. We became friends over the 48 hours we drove back to NYC and then from that point on, he was down. He was open and receptive.”

Perhaps the most light-hearted installment of the series, Listening to Kenny G asks how the titular saxophonist occupies both one of the most successful and simultaneously disliked musicians of all time. Ironically, director Penny Lane never intended to make a music documentary, but after she met Bill Simmons and his team, became interested in the possibility.

“To me, the most interesting thing is how deeply music is tied to our sense of personal and social identity…I spent years as an art professor and debating with students about what makes art good or bad and knowing that, even though I was the professor, there really isn’t an objective answer. Those ideas came together in the figure of Kenny G. He was a vessel for that idea. But then getting to know him, his personality is so special and unique and the film evolved and got a lot better as I go to know him. I wanted more and more to bring people into contact with this weird guy I had gotten to know.”

Mr. Saturday Night follows Australian entrepreneur Robert Stigwood and his lasting impact on the traditions of American cinema and the record industry. Director John Maggio explains his initial fascination with Stigwood and the layers he kept peeling back on this “fascinating, closeted gay character who lived this outsize life in the entertainment world but spent most of his life on a yacht in the Caribbean, throwing parties, having orgies, doing all sorts of crazy stuff.”

Maggio continues, “He came out of nowhere and suddenly had all these hits on Broadway…then he decided to turn to Hollywood…I mean the guy, he basically created the modern soundtrack.”

He explains his process: “To capture that moment, I did it all archivally. There’s no talking heads that pop up. I wanted the film to almost feel encased in amber that way…For a moment in time, in the mid 70s, [Stigwood] owned Hollywood.

The final installment of the series, Juice WRLD: Into the Abyss explores the tragically brief, but lasting legacy of rapper Juice WRLD. According to director Tommy Oliver, the film had unexpected beginnings and evolved into a monumental task of archival footage organization to ultimately tell “a story that felt inevitable, but also enough of what was going on so you understood him.”

Oliver chuckles a little recalling the “crazy journey” and its start. “Little did I know that I’d get dumped hundreds of hours of unorganized footage that wound up becoming just, a gem…The deeper we got into it the more I realized there was a tremendous opportunity to be able to tell the story from [Juice WRLD’s] own perspective and so he had the ability to speak for himself.”

In the editing bay, Oliver recalls feeling like he was “reading someone’s diary who had passed away.”

Music Box spans a diverse range of subjects and voices, but Simmons explains that each film is tied together because “each one answers a question in its own way,” and never the question you expect.

The Music Box collection is currently streaming on HBO Max.

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Written by Emilia Yu

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