Bill Simmons's Music Box

Bill Simmons has a way of reading autobiographies. "I always skip ahead seventy-five pages," he says. "I care about the stuff that I know about — when they were becoming famous or when they were famous or after they're famous. I don't care about what second grade was like."

Simmons's approach to consuming life stories is notable because it dovetails with the backstory of 30 for 30, the series of ESPN documentary films he cocreated with Connor Schell. On a personal level, that series marked Simmons's entry into television, but on a much larger scale, it changed how the world consumes nonfiction films about sports. Instead of following the long-established format of what Simmons calls the "beginning-middle-end" biopic, filmmakers were asked to drill down on an incident, a window of time or a turning point, whether for a sport, a team or an individual athlete.

This was also part of Simmons's spiel when he went to HBO a few years ago to pitch Music Box. "We told them we wanted to root [each documentary] in a moment," he says of the series, which was produced by his company, Ringer Films, and debuted last year.

Of the six installments — each created and executive-produced by Simmons — four focus on musicians: singer-songwriter Alanis Morissette (Jagged), jazz saxophonist Kenny G (Listening to Kenny G) and rappers DMX (DMX: Don't Try to Understand) and Juice WRLD (Juice WRLD: Into the Abyss). One episode is devoted to three ugly days at the second Woodstock festival (Woodstock 99: Peace, Love, and Rage), and another, Mr. Saturday Night, explores how entrepreneur Robert Stigwood was among the first to realize that a soundtrack could be used as a cross-promotional tool for a film. In December, HBO announced Music Box has been picked up for a second season.

Penny Lane, who directed Listening to Kenny G, a witty examination of popular taste hiding inside a bio-doc, immediately understood Simmons's desire to up-end music docs. 

"That was one of the reasons I wanted to work with Bill in the first place," says Lane, whose reputation for unconventional documentary subjects and stylistic irreverence (Our Nixon, Hail Satan?) made her an ideal fit. "He correctly diagnosed a problem with the form that is very common, which is that when you're making a film about a famous person, or a band or whatever, it feels like [it has to be like] a Wikipedia page. It's weird, but you feel like you're required to include everything that ever happened. We were both resonating on avoiding the trap of the complete biopic."

Describing his relationship with a director during production of a documentary, Simmons turns to prizefighting. "You're basically their corner man in a boxing match. They're coming back to the corner and you're telling them, 'All right! You're doing great. Keep that left hook coming!'"

During his years at ESPN, he did everything he could to make 30 for 30 as filmmaker-friendly as possible. Though HBO is now regarded as a standard-bearer for high-quality TV documentaries, Simmons still felt he needed to dig a protective moat between the premium cable channel and the Music Box directors. "People don't understand sometimes — especially if they're in an executive position — that when you're getting notes from all different directions, it can really screw a filmmaker up. They can get really frustrated," he says. "We love working with HBO. But we tried to centralize the notes process by running everything through us."

Before he became a television impresario, Simmons revolutionized online sports journalism with his breezy, seemingly off-the-cuff writing style. Yet he was a practitioner of endless drafts, a writer who would tinker with a column until it sang. Little wonder, then, that he loves the editing stage of a documentary, immersing himself in cut after cut and throwing out suggestions. "You're going, 'Are you sure? Do we need this?' and 'If you take this out, here's how this unfolds.' That, to me, is my favorite part," he says.

Even when it comes to feedback, Simmons tries to be as unshowbiz as possible. "[Bill is] very blunt, very direct. There's not a lot of dancing around stuff like a lot of Hollywood people do," says Lane, who remembers butting heads with him about a gorgeously shot piece of concert footage she had at the beginning of her Kenny G doc. 

"Eventually he was like, 'You think it's interesting because you know so much about Kenny G,'" she recalls. "Most people are not coming into it like that. They're just like, Is this a Kenny G concert documentary? Guess I'll watch something else!" Lane ended up moving that footage to later.

"He'll love this if you print this," she says, "but even the notes I fought and fought and fought, I ultimately had to admit he was right. That's very annoying for me, but true."

When Schell was an executive for ESPN Content Development back in 2005, he noticed that Simmons's knowledge about sports, pop culture and music seemed to have no bottom. Simmons, who'd just returned to the cable sports channel after a year and a half as a comedy writer on a then-new ABC late-night series, Jimmy Kimmel Live!, also seemed infinitely curious about how to use TV sports to explore wider subjects.

"He was really interested in understanding more about programming on ESPN and how he could affect that landscape," Schell says. "It started with the premise that sports is one of the last bastions of American culture that truly brings everybody together, that there are these cultural moments that unite us and can be used as a window to talk about tragedy or race, all sorts of things. And that sports is your way in. A lot of our relationship in the beginning was just, 'How come no one's ever done this?' and going back and forth on it."

As it happens, in 2007, ESPN's documentary arm was getting hammered by, of all things, HBO Sports, and Simmons felt that he'd identified ESPN's deficiency.

"We were doing too many different kinds of films, just kind of shooting them out like a T-shirt cannon," he remembers. He sent a short memo saying as much to the top brass. "My point was, 'We have to do something that we can brand in a certain way, that has a certain level of quality, because we should be a leader in the space.'" His corrective? To celebrate the groundbreaking sports channel's thirty-year anniversary by commissioning thirty hourlong films by thirty top filmmakers, all of whom would be given free rein.

To be clear, even Simmons admits he didn't know much about making television when 30 for 30 got the green light. But, as they started isolating important sports stories and reaching out to filmmakers, Schell says, it turned out that Simmons had other qualities that made up for his lack of hands-on experience. 

"In a really good way, Bill's not limited by what other people might think is impractical," Schell says. "He'll have an idea and get really excited about it. It's infectious." As a sportswriter and fan himself, Simmons also knew what his fellow diehards were interested in — and it wasn't warmed-over legend-burnishers like Tom Brady being the 199th pick in the 2000 NFL draft.

"[Simmons and Schell] didn't want to tell the story of the 1950s Yankees again, stories that had been told, like, a hundred thousand times," media critic Noel Murray says. "They were, like, 'We're going to tell a story about the USFL or the time the Baltimore Colts left Baltimore.' They also tried to get some actual filmmakers like Barry Levinson, Peter Berg, Steve James. They got actual voices with real perspectives to make actual films, not just something that would be a promotion for a team or player."

What began as thirty episodes expanded into multiple seasons and spawned spinoffs like the Emmy-winning 30 for 30 Shorts. But after almost fifteen years at ESPN, Simmons felt things shifting. He points to This Magic Moment, a 30 for 30 film about the Orlando Magic's Shaquille O'Neal and Penny Hardaway, which began as a Simmons passion project but eventually felt stage-managed. "By the time we actually did it, Shaq and Penny were executive producers," Simmons says. "We had to have this false moment at the top. I stopped watching the cuts. I was like, 'This is not the direction we should be going in as a company.'"

By May 2015, Simmons was out, fired by ESPN's then-president John Skipper, for all manner of reported reasons: Simmons was overpaid, he'd gone on a radio show and taken shots at NFL commissioner Roger Goodell, he couldn't keep his opinions to himself. Along with Simmons went his popular podcast, The B.S. Report. Months later, ESPN pulled the plug on the sports and pop culture website Grantland, a writers' haven he'd launched in 2011 and had run as editor-in-chief.

Within three months, Simmons had moved to HBO, where he hosted a short-lived talk show, Any Given Monday with Bill Simmons. Many Grantland writers migrated over to his new website and podcast network, The Ringer. A year and a half later, Simmons launched Ringer Films. His first project for HBO was André the Giant, a documentary on the seven-foot, four-inch French-Bulgarian pro wrestler. In 2020, Simmons sold The Ringer to Spotify for, reportedly, nearly $200 million, making him, as Forbes put it, "Podcasting's First Big-Money Superstar." The Spotify deal included Ringer Films.

Back in his Grantland days, Simmons had stumbled across a two-part authorized documentary directed by Alison Ellwood called History of the Eagles. He'd never much enjoyed the '70s band, but Simmons became obsessed. He kept History of the Eagles on repeat and eventually wrote a 6,000-word article about why he considered it one of the best music documentaries he'd ever seen. In the end it got him thinking about how to make music documentaries that would be as universally riveting as a 30 for 30 film at its best.

It turned out, Simmons says, making longform nonfiction films about music is "a thousand times" more complicated than making them about sports. "You have to deal with managers. You have to deal with estates. You have to somehow get [the rights] to the music. You probably have to get participation from the artists. There're all these variables — and the artists could flake."

Part of what made him think he could pull it off was a bit of information he'd learned from former Eagles manager Irving Azoff: since the 2013 release of History of the Eagles, the band had been touring again and its library on iTunes was showing greater traffic. "I thought that was really interesting," Simmons says. "If the film is good enough, there're ancillary benefits that matter. That's how we tried to convince people to do it."

In assembling a lineup of Music Box subjects, Simmons wanted to tell both lesser-known stories of older artists and to introduce present-day musicians to grownups. His thinking went like this: "The way we took HBO Sports' lunch [with 30 for 30] was that they were doing old documentaries — Joe Louis, Joe DiMaggio, Ted Williams. People my dad cared about. Nobody was doing documentaries on the people I cared about."

Everything else, though, was up for grabs. Kenny G was Lane's idea. Then Simmons heard that director Christopher Frierson had been following rapper DMX since his release from prison in early 2019. Looking for a contemporary musician, Simmons discovered that Juice WRLD's label, Grade A, had "basically taped the last two years of his life" before the emo-rapper died of a drug overdose in 2019. (DMX died in 2021 of a cocaine-induced heart attack.)

Simmons knew that his son, a big Juice WRLD fan, would immediately spark to such a rare inside look. What Simmons wasn't expecting was how he himself responded each time director Tommy Oliver delivered a new edit about the late rapper, a gifted, sweetnatured teen who was addicted to liquid codeine and sang about battling anxiety.

"It affected me more than any film I've ever worked on," Simmons says. "Every time I saw a cut, I was affected for the next couple hours. It was never a drug story for us — it was always a mental health thing. Because that's what he sang about and that's what resonated with kids — the mental health part and being depressed."

As it turns out, the Juice WRLD documentary is also one of Simmons's teenage daughter's top Music Box picks, along with Alison Klayman's Jagged, about Morissette's spectacular rise to fame with her 1995 album Jagged Little Pill. Judging from a statement Morissette released in September, in which she declined to support the film, her own review was less glowing.

Asked about that reaction, Simmons chooses his words carefully. "When somebody is telling your story, it's going to hit you in different ways," he says, adding that while Morissette was sent multiple cuts and was allowed to give her input, she had no final editorial say.

But he's sticking with his faith in the ancillary benefits Irving Azoff identified. "My daughter is sixteen," Simmons says. "She plays the piano. She didn't know anything about Alanis. She watched [Jagged] with me. Then she listened to Alanis for three weeks and started playing her music on the piano. It's the best possible film. I think Alanis will see that at some point. I think the film is going to win.

Season one of Music Box is available on HBO Max.

This article originally appeared in emmy magazine issue #3, 2022, under the title, "Backstage Pass"

Season-one directors of Music Box discuss how they approached their subjects.