The end of the iTunes era: The life and death of Apple’s curator-in-chief
The last time music engineer and producer Bill Inglot spoke to his friend Gary Stewart, Inglot was in a Baskin-Robbins parking lot, eating an ice cream cone.
“It was a nice April day, so I sat in my car and opened the sun roof, and the phone rang. It was Gary.”
That wasn’t unusual. The two had been friends for decades — went to Hollywood punk shows together as teens, worked alongside each other during their wild run at famed reissue label Rhino Records across the 1980s and ’90s and still spoke three or four times a month: about favorite artists who never quite got their due, about shared memories of long-ago gigs and about the hazards of growing old in a business that prizes the new above all else.
“We always had fairly frank conversations,” Inglot says. “If you’ve known someone for 45 years, you’re going to have dark days and you’re going to share them with each other. But not on that day, and not at that time.”
A day later, on April 11, just after midnight and as at least one onlooker watched from the street below, Stewart, 62, jumped to his death from the roof of a downtown Santa Monica parking structure.
Over his four decades at Rhino Records and Apple, Stewart left his mark as one of the greatest curators the music business had ever known, cataloging, packaging and recontextualizing forgotten and overlooked swaths of rock history, much as legendary anthropologists Harry Smith and Alan Lomax had done for folk and for blues.
His knowledge was so deep that former Apple Music colleague Brian Rochlin called him “unintentionally intimidating” when it came to discussing pop culture. “No matter how much you loved something,” Rochlin said, after talking to Gary, “you were going to find out that you knew a lot less than you thought you did.”
But on that April night, a life’s worth of obsession — the millions of facts, opinions, melodies and connections stored in his memory — vanished.
When I was a kid, reissues were little cheap LPs. They were considered car-wash purchases. Gary elevated them to high art.
When word spread of Stewart’s suicide, his friends rushed to social media to pay tribute. Calling the news “impossible to conceive of,” music publicist Cary Baker recalled that Friday as “a web of emails, calls, texts and so many Facebook messages.” Mayor Eric Garcetti described his and his wife Amy’s affection for Stewart, writing on Twitter that he was “one of the funniest, most humble people we knew.”
Musicians Elvis Costello and Billy Bragg, actor Michael McKean, Blondie drummer Clem Burke and many others celebrated their friend and mourned his fate.
Stewart had lived with depression throughout his life, but he kept it a secret from all but a few. When Inglot got the news, he started replaying their phone call for warning signs but came up blank. “However I thought things were going to play out for Gary, it wasn’t this. I feel like he had another 20 years of being passionate about stuff.”
After his death, more than one person called Stewart a real life George Bailey, conjuring the despairing banker who contemplates suicide in “It’s a Wonderful Life.” But Stewart didn’t have Clarence to stop his fall.
“I don’t think it was any secret to Gary how admired he was,” says Baker, a longtime friend. “But somehow that wasn’t enough.”
Rewrote rock’s canon
Gary Stewart never married and had no kids. But he had an enormous community of friends. Inglot and Baker were among those who attended Stewart’s 60th birthday party in 2017, which drew 650 people to a Santa Monica hotel ballroom and featured performances by San Francisco power pop band the Rubinoos and soul singer Swamp Dogg.
Drummer Danny Benair was there and was awed by the turnout: “He’s the only person I know who’s filling ballrooms and he’s not some rock star.”
Across 45 years, Stewart had changed the way the culture hears music. By the time he was named executive vice president of A&R for Rhino Records in 1992, he’d already overseen the creation of hundreds of “best of” CD compilations and anthologies. At Apple’s iTunes, he introduced Essentials playlists long before streaming services upended the business. Philosophically, he may have done more to shift the listening experience from the single-artist LP and toward a compilation or playlist mentality than any other figure in music history.
Stewart’s Rhino compilations ignited the reissue business. Not only did they earn much-needed royalties for countless lesser-known musicians, but they rewrote the canon of popular music, offering counterprogramming to the codified tastes and values of the baby boomers in power.
For his 1993 multi-volume “D.I.Y.” series, Stewart wrangled explosive punk and post-punk songs onto CD compilations that served as both historical documents and aesthetic arguments. “Teenage Kicks: U.K. Pop I,” connected mid-’70s punk and pub rock. A U.S.-focused set illustrated the depth and range of regional punk and power-pop scenes. Stewart’s Los Angeles volume, “We’re Desperate: The L.A. Scene 1976-1979,” gave voice to the artistic range of Southern California punk.
“He was ideally suited to the way music has gone,” says Elvis Costello, who worked with Stewart on numerous projects over the decades. “If you curate music properly, people can stumble across beautiful songs that may have otherwise been buried on albums in cut-out racks.”
As the older of two siblings growing up on the Westside, Stewart was a culture freak. With the encouragement of his movie-going, music-loving parents, Stewart and his brother, Mark, collected comic books, monster cards, stamps and coins. As Gary hit adolescence in the late 1960s, his brother recalls, he fawned over records by Creedence Clearwater Revival, the Jackson 5 and their favorite band, Three Dog Night.
“His life before Rhino was his record collection,” Mark Stewart says. Gary used to invite “the whole neighborhood” over to play records as Gary shared trivia gleaned from the pages of Creem, Circus and Rolling Stone magazines. When Rhino Records — the 3,000-square-foot record store that would eventually spawn the label — opened in Westwood in 1973, Stewart was one of its original customers. Along with Tower on the Sunset Strip and Aron’s on Melrose in the pre-Spotify era, Rhino was the closest thing to the so-called celestial jukebox that West Los Angeles had, and its clerks served as the search engines.
“The biggest music nerds would hang out at our store because in those days there really weren’t a lot of stores for record fanatics,” recalls Rhino Records founder Richard Foos. “Gary came in to the store one day, and I think he never left.”
Alongside Foos, and other crucial early Rhino employees like Harold Bronson and Jeff Gold, Stewart worked his way up to store manager, voraciously logging music, liner notes and opinions in his internal database. In the mid-1970s, Rhino became a label as well, pressing and selling records by a ragtag collection of artists including Wild Man Fischer and Allan Sherman before moving on to repackaging the catalogs of famous and semi-famous artists from the ’50s, ’60s and ’70s.
During the ’80s, as vinyl ceded the market to compact discs, revenue soared. Stewart ascended to vice president of A&R, and did so during one of the most profitable decades in music business history. His former Rhino co-workers say Stewart was the guiding force in Rhino’s success.
“He helped write the book on the current-day reissue business,” Baker says. “When I was a kid, reissues were little cheap LPs. They were considered car-wash purchases. Gary elevated them to high art.”
Rhino continued its success through the 1990s, producing series including year-by-year Billboard hit single collections and the transcendent “In Ya Face” funk compilations, plus career-redefining sets on Ray Charles, Curtis Mayfield, Otis Redding and John Prine. The four-CD “Aretha Franklin: Queen of Soul” collection sold more than 100,000 box sets alone.
These days, says Inglot, “if you sell 50,000 of anything you’d break out the party hats.”
Rhino sold to the Warner Music Group in 1998 and founders Foos and Bronson departed a few years later. Stewart stayed on after they left. Never much for corporate hierarchies and missing many of his peers, though, as the music business collapsed post-Napster, Stewart too put in his notice.
A call from Steve Jobs
In 2004 while Stewart was working as an independent producer and consultant, Steve Jobs called. Stewart didn’t recognize the name and told his assistant he’d call back.
Reminded that this guy was transforming the world, Stewart reconsidered and took the call. Jobs told him the company was looking for a senior level executive for the iTunes project. The former Rhino executive joined Apple that year in the newly created position of chief musical officer.
Stewart’s job was to oversee and organize content for the millions of downloadable tracks within the company’s music platform. Specifically, he helped advance the digital landscape by cementing the idea of hand-curated Essentials playlists. They’ve since become a defining feature of the streaming age.
“Gary told me, ‘The same thing I was doing on record I’m now doing digital,’ ” Baker recalls. “He was writing the template for the future.”
Frustrations over his changing job responsibilities — Apple had stopped supporting Essentials — led Stewart to depart iTunes in 2011.
“He had done very well, economically, there,” Gold recalls. “At some point he decided, ‘I’ve done what I’ve done and they’re not interested in my vision.’ ”
For the next five years Stewart freelanced as an independent consultant. In 2016, David Dorn, a former Rhino colleague and then senior director of Apple Music, asked Stewart to return to work on curation at the newly unveiled streaming platform.
“We’ve got 50 million songs and we’re in a playlist world,” Dorn, who’s now a senior director in the company’s mapping division, recalls telling him. “I couldn’t think of a person who was better suited to help us create that context and storytelling.”
Stewart returned to Apple for two more years. He and a team of selectors helped build many of the thousands of playlists that Apple Music subscribers continue to access daily. He put in his notice in October 2018. Stewart told a former Apple Music co-worker that he’d accomplished his goals, but that “what they wanted him to be doing next wasn’t what he wanted to be doing next.”
“Gary had very exacting standards,” Gold says. Apple Music “stopped being fun for him. He couldn’t bring himself to sell out, which is how he saw it.”
Music publicist Fiona Bloom recounts Stewart’s growing frustration with an industry that no longer valued his kind of inexhaustible expertise. “We talked a lot about how kids could just come up and take over a role that people spend years mastering — not paying their dues, not working those 10,000 hours. It was disturbing to him.”
‘They were moving in another direction’
In the hours before his death, Stewart participated in a conference call with colleagues from Liberty Hill, a community nonprofit advocating for economic, racial, LGBTQ and environmental justice.
The group’s co-founder, Sarah Pillsbury, says the conversation involved strategies to “end juvenile justice as we know it, and to engage our donors and contact legislators.”
Across his years at Rhino and Apple, Stewart devoted his time to social justice causes, including Liberty Hill; the Community Coalition, a community-driven South L.A. nonprofit on whose board he served; and the Los Angeles Alliance for a New Economy. Stewart willed the majority of his estate to the trio of nonprofits, according to his brother, Mark Stewart.
That was just like Stewart. His reflex was to share. Those invited to his annual Loser’s Christmas parties, which he held for more than 30 years, remember celebrating and commiserating with a perpetual bachelor eager to connect.
“He loved discussing things, both in person or on the phone. That’s where he shined the most,” Bloom says. “You go to a show, there’s loads of people you know. But then you go home and you’re sleeping in your bed alone. It can be quite lonely.”
Pillsbury recalls that over the years they had spoken about the difficulties of getting old in the entertainment business. One of the biggest fears they shared, she says: “People are thinking about me in the past tense.”
It didn’t help that companies like Apple, Spotify and YouTube have come to rely on algorithms to recommend music to its users. Stewart’s obsessive knowledge of and passion for rock history was no longer needed.
One labor-intensive Apple project Stewart worked on, for example, School of Rock, presented the history of the music across a few dozen chapters and sets of playlists. When it failed to attract enough user interaction, the initiative was archived into a virtual lock-box.
“They were moving in another direction,” Rochlin says.
Corinne Bendersky, a professor at UCLA Anderson School of Management, says she’s seeing “a lot of concern about AI and algorithms replacing white-collar jobs,” similar to what happened with the introduction of robotics into assembly line work.
Bendersky notes that Pandora, Apple Music and Spotify’s tools are similarly disruptive, even if they’re tackling jobs considered “more artistic or taste-based,” as she puts it. “That trend,” she says, “is very much likely to continue.”
Some of Stewart’s closest friends say that in the weeks prior to his death he had asked for, and received, help and advice.
“[H]e was depressed,” Jeff Gold wrote on Facebook. “He was lamenting not having a job, relationship, having spent too much of his Apple money and not knowing what the next chapter of his life was.”
Gold recalled a meditation retreat Stewart attended — “which he didn’t love,” Gold wrote — and “a very frank discussion” they’d had over lunch a few months before. The two talked about the drug ketamine and its potential in treating depression. Gold sent him a link to a film involving MDMA treatment for PTSD survivors. Stewart replied two days before his death that the video had given him a deeper understanding of the approach.
As news spread of his passing, friends gathered to mourn their loss and learn more about Stewart’s last days. Some got together for an impromptu Seder, which helped those who felt like they’d missed signals or let down their friend.
David Gorman, who worked with Stewart at both Rhino and Apple, compared Stewart to “the quintessential Jewish grandmother: ‘Don’t worry about me, I’ll sit here alone in the dark,’ ” he said with a warm laugh.
On June 1, the Skirball Center will host an afternoon memorial in Stewart’s honor. Co-hosted by Rhino’s Bronson and Foos, Jeff Gold and artist manager John Silva, the event will be open to the public.
In May, his friends gathered for a private memorial hosted by McCabe’s Guitar Shop, a few blocks from Stewart’s home. Between shared memories, attendees watched musicians including Billy Vera, Cindy Lee Berryhill, Chris Stamey and Peter Holsapple of the dBs and Chuck Negron of Three Dog Night celebrate a life.
Vera, who scored Rhino’s only No. 1 record with “At This Moment,” remarked that his deal would never have happened without Stewart. Noting the volume of sad songs shared from the stage across the night, Vera protested, reminding the crowd of Stewart’s approach to life. “Gary had a sense of humor. He wanted us to be happy, so let’s be happy.”
For many of Stewart’s friends, that’s easier said than done. The whole thing makes no sense.
“Every sorrow can be borne if we can tell a story about it,” says Pillsbury, quoting writer Karen Blixen. “But sometimes you can’t tell a story, because there’s one unknown, and there’s only this tragic ending.”
12:56 p.m. This article was updated with additional details about a June 1 memorial service.
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