Huge crowd at outdoor stage that reads "Woodstock 99"Huge crowd at outdoor stage that reads "Woodstock 99"

Bill Simmons Wants to Make Rewatchable Music Docs

By Cande Duran

Music Box creator Bill Simmons is bringing a different approach to the traditional music documentary, starting with Woodstock 99: Peace, Love, and Rage.

When Bill Simmons created the popular 30 for 30 documentary series for ESPN, he set out to break the traditional sports documentary mold, which he says tended to follow the chronological timeline of a person’s life, and instead make documentaries telling the stories of specific moments or windows in time. Now, Simmons is bringing that philosophy to the world of music docs with Music Box, a new documentary series for HBO. Produced by Simmons’ company, The Ringer, Music Box is a collection of six documentary films exploring pivotal moments in the music world, each helmed by a different director and focusing on a different topic. Simmons spoke with HBO about Woodstock 99: Peace, Love, and Rage, the first film in the series to premiere, and offered a glimpse of the other five films to premiere later this year.

HBO: The Ringer originally did a podcast about Woodstock ’99 called Break Stuff. What drew you to that story, and what made you decide to adapt it into a documentary?

Simmons: That got pitched to us as a podcast, and to us it’s the same question whether a podcast or a documentary, or anything: Is it a good story? The Woodstock ‘99 thing was kind of perfect in the sense that people remembered it, but they don’t really remember it. You’re going backwards in time and you’re reliving something, but you’re also discovering things.

We actually thought it would be even better as a documentary than it was as a narrative podcast, because of the visual stuff. Fred Durst is a complicated figure in this film, but seeing when he performs, you really feel the energy from the crowd.

HBO: Definitely, that scene with all the people in the mosh pit, it’s like an ocean.

Simmons: Yeah, it was interesting watching cuts for it, too, because it was during the pandemic, and there hadn’t really been crowds for almost a year. You just kind of forgot the power of a crowd, for better or worse, and I think that’s a lot of what this documentary is about. So visually, having the footage, being able to actually see the destruction and how the event kind of devolves over the course of three days, I thought it was great and it turned out even better than I hoped.


“You just kind of forgot the power of a crowd, for better or worse, and I think that’s a lot of what this documentary is about.”

- Bill Simmons


HBO: Were you anywhere near Woodstock ‘99 while it was happening, or do you have a clear memory of it?

Simmons: I do actually. I did not go, but I had an illegal cable box at the time in Boston where I would get all the pay-per-views, and Woodstock ‘99 was a pay-per-view event. It was on for three straight days, and it was kind of like watching a car crash.

I remember watching the [Red Hot] Chili Peppers performance. They were cutting to fire and stuff, and you’re like, “What is happening there? Are these people going to be alive?” The fact that it was a pay-per-view was supposed to be one of the big gimmicks that made this feel like a modern event, and if anything, it kind of captured all the horrible stuff that was happening.

HBO: A lot of people might not remember this event. How do you think someone with no prior knowledge about Woodstock ‘99 will connect to this film?

Simmons: We thought about that with all the films we did for this series. I think the mistake people make, especially with music documentaries, is most of these decisions to greenlight documentaries, and most of the documentaries themselves, are made by people that are a little bit older, and they tend to concentrate a lot of the ideas on people from the ‘70s and the ‘80s, because those were people they cared about. As we put the series together, in my head I was always like, “Would my daughter be interested in that? Would my son watch this? Would my dad want to watch this?” You want to hit all types of people and I think with Woodstock, even if you don’t remember it, you’re gonna know a lot of the bands in there, you’re gonna know what it’s like to go to a festival. But, just in general, if you’re telling a good story the right way, you can get people to watch.

HBO: Some of the people in the documentary really criticize the mythology around Woodstock ‘69 and the original Woodstock documentary for being too nostalgic. Is that something you have to keep in mind when you’re working on a doc about something you feel a personal connection to?

Simmons: A lot of times that happens, especially in music, because the projects are being propelled by the side of the artist. I always call them infomercial docs, or documercials. They’re documentaries, but they’re really a brand play for the artist, and we really wanted to avoid that. The six that we chose for this series, we just kept thinking about a moment in time, some sort of window, some sort of reason you can explain this doc in a sentence, versus like the traditional type of doc.

Concert-goer raises her fist as she trudges through the mud

HBO: What was the inspiration behind Music Box?

Simmons: I’ve been thinking about this idea since 2014, and the big influence for me was a documentary about the Eagles. I thought it was the best music documentary I’d ever seen, and what was interesting to me was that it was rewatchable. I remember I watched it like four times that summer, and the best 30 for 30s we did are the ones that you could watch five, six times. That Eagles doc really made me think there is a way to do what we did with 30 for 30, but with music. There’s a way to make rewatchable, high-end, awesome docs, and put them under the framework of some sort of series.

HBO: What do you think it is about music that makes it such a good entry point into the larger cultural landscape?

Simmons: It’s a little like sports, but it’s even better than sports because it kind of reflects whatever’s going on at the moment. That’s what’s so fascinating about this Woodstock doc is, for better or worse, it reflects 1999. Mostly worse, but I think, especially when you think about how the country has evolved in the last few years, and you compare it to 1999 and some of the stuff people were getting away with, it’s pretty jarring. For somebody like my daughter, who is now sixteen and sees the world in a different way, when she watches something like that she’s kind of like, “How was this allowed to happen?” I think that’s one of the reasons it’s a good doc, it doesn’t try to hit you over the head with the themes, the themes are there.

HBO: The other five documentaries are about such different topics, you have Alanis Morissette, Robert Stigwood and Saturday Night Fever, DMX, Juice WRLD, Kenny G. Can you tell me more about that process of choosing the six Music Box films, and how they came together?

Simmons: A big part of the pitch was we wanted different filmmakers for each one. I remember when we were trying to do the first 30 for 30 in 2007, 2008, we couldn’t find thirty filmmakers, much less thirty that could do a documentary at the quality that we wanted. There’s a whole generation now of filmmakers who grew up as kind of sons and daughters of the documentary boom. On top of that, you have footage from people just filming the artist or whoever on their phone, something that’s uniquely of the last twenty years — you’ll see that in the Juice WRLD documentary. So we approached it by meeting with as many talented people as we could, and trying to give them the runway to do something they’re super passionate about.

We felt like the hole in the music documentary space that we wanted to fill was kind of skipping the whole arc of somebody’s life and concentrating on specific moments. That was a big thing with the Alanis doc. That entire documentary is about one album. We give her backstory, and you learn everything you need to know about her, but it’s really about eighteen months in somebody’s life when their whole life changes. Each documentary we did has a point, and that’s why it took so long to find six that we really liked and could do.

HBO: The Kenny G film really stands out to me in that bunch, I’m so excited to see that one.

Simmons: We wanted to pitch an idea to the director Penny Lane, who did a documentary called Hail, Satan, but she was like, “You know, I have this other idea, it’s about Kenny G.” I was like, “Kenny G? What would that idea be?” And it was one of the best pitches I’ve ever gotten. She was really intrigued by the fact that Kenny G was the most successful new Jazz person ever, while at the same time becoming kind of a punchline, but he was also in on the joke. A lot of people don’t see the chessboard that way, but she saw it and she ended up making a great film. It’s really quirky, and it’s definitely memorable.

The Robert Stigwood doc is all archive. Those are the hardest docs to make, to go through all that footage, to know what to concentrate on. You could end up doing an eight-hour doc. It’s almost like a piece of steak. You don’t want it to be this giant porterhouse steak with fat all over, cut into it you don’t know if you’re gonna get a good bite or not. You want it to be a filet mignon.

The DMX film was the only one we didn’t make from scratch. It was actually a finished cut we bought about a year ago, but we felt like there were ways we could expand, and we just really liked the director [Christopher Frierson]. It’s interesting how that one evolved. [DMX] passed away a few months ago. Watching the outpouring for him, and then thinking of this documentary we have, which is now completely different when you watch it, was a pretty bizarre experience. But that one is really powerful, and I think the people who love him will be happy with it.

We put a lot of thought into the series itself and how the six films would make sense together. Even if they’re done by six different filmmakers, in six different ways about six different things, my hope is that it will make sense collectively.

Discover more about Woodstock 99: Peace, Love, and Rage and the Music Box series here.

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