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 reissued 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.

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.

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.”

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.”