Bey, working the Apollo crowd on December 21 Shahar Azran/Apollo Theater

Quiet as kept, 2016’s angel of death claimed one last casualty in December before finally getting the fuck on. For millennials raised on lyrically dense late-Nineties hiphop classics like Mos Def and Talib Kweli Are Black Star and Mos Def’s seismic debut, Black on Both Sides, the recently announced retirement of Yasiin Bey marked the death of backpack rap itself. Ten days after his 43rd birthday, Bey (f/k/a Mos Def, Dante Beze, and Dante Terrell Smith) performed at the Apollo Theater; the December 21–22 run in Harlem, along with a stay from December 31 to January 2 at the Kennedy Center in D.C., marked his farewell to music after years of expatriate living in South Africa.

Dec 99th — a project with producer Ferrari Sheppard — dropped the same night as that first Apollo date; Negus in Natural Person and As Promised (another collaboration, this one with producer Mannie Fresh) are due soon. For all its Ragnarök upheaval, 2016 managed to gift us all some grown-up hiphop for the aunties and uncles at the party: A Tribe Called Quest’s astounding comeback, We Got It From Here…Thank You 4 Your Service; De La Soul’s Kickstarter-funded and the Anonymous Nobody…; El-P and Killer Mike’s Run the Jewels 3. So Yasiin Bey’s bow-out wasn’t strictly necessary from an ageism point of view. But anyone paying attention has long known the former Mighty Mos Def just wasn’t made for these times.

“If people are trying to be famous, then they’ll do one thing,” Bey told me way back in 2000. “If people are just trying to support themselves and put their music out and do so in a way where they control what they create — they control how it’s presented, they control the bulk of the money that they get — and that’s what they wanna do, they’re gonna do another thing. Some people wanna achieve notoriety so they can use whatever acclaim or light that they have to shine it on broader issues, donate to something other than themselves. At the end of the day, it’s all based on people’s intentions on what people are trying to do.”

Seventeen years later, how hard is it to pinpoint Yasiin Bey’s intentions? Shades of Netflix’s Luke Cage, “always forward, forward always” could be the tagline for Bey’s entire career. “Umi Says,” the positivist anthem that’s one of his most recognized songs, finds him singing soulfully, carving out the path in hiphop trod since by Drake, Future, Childish Gambino, and loads more. At the sold-out Apollo, he switched up lyrics in an emotional performance of the song, chanting a self-accepting “I’m perfect as I am” (in lieu of “I ain’t no perfect man”) into his customized crimson microphone. I sat next to a style editor whose wedding song was (swear to god) “The Panties” — the Marvin Gaye–styled come-on Mos Def crooned through in ’09 — who rejoiced when he introduced it. His rock band Black Jack Johnson (guitarist Dr. Know, keyboardist Bernie Worrell, bassist Doug Wimbish, and drummer Will Calhoun, all already famous from Bad Brains, P-Funk, and Living Colour) laid tracks on 2004’s The New Danger, presaging hiphop musical mash-ups like Yeezus and Saul Williams’s The Inevitable Rise and Liberation of NiggyTardust!

Mos Def always went left. The former poster boy of Nineties boom-bap preservationist rap refused to ride that till the wheels fell off. He sang. He rocked out. He left the United States for Cape Town in 2013; after issues arising over his use of a so-called world passport, he’s no longer allowed to return to South Africa. (“America’s a very challenging place for me,” he explained two years back about leaving the U.S. “Given the current social, political, economic climate…the type of creativity that I like to have, it’s very difficult for me to produce that here.”) His later albums — 2006’s label-deal-closer, True Magic, and, three years later, The Ecstatic — revealed nearly no commercial considerations at all.

Yasiin Bey touched on so many styles across his five-album discography that predicting the sound of Dec 99th, this latest release, would’ve been impossible. Several songs start off with a ceremonial bismillah or straightforward dedications to Allah. It sounds musically moody and minimalist (eight songs, one reprise, and an instrumental), an austere woodshed effort akin to Q-Tip’s Kamaal/The Abstract. To be less kind, it’s an experiment you’ll likely be hearing in the background of Williamsburg hipster boutiques. News of the Mannie Fresh alliance, As Promised, dates back to 2012; that project surely involves more standard rhymes and rhythms. Same for Negus in Natural Person, newly announced last month as a more proper follow-up to The Ecstatic.

His Apollo shows were billed as Yasiin Bey & Friends, but audience-expected guests like Talib Kweli and De La Soul never showed. Slick Rick the Ruler appeared to a standing ovation on “Auditorium” during night one, Pharoahe Monch spat “Oh No” and “Simon Says” both nights — and that was it. Bey never rocked his biggest hit, the gluteus maximus shorty-rock ode “Ms. Fat Booty,” and closed out with a trio of Dec 99th tracks. “I can appreciate entertainment, but I’m over it if it’s a place you can’t be earnest,” he said at one point from a rose-petal-strewn stage, flanked only by his DJ. “I don’t always want to be dazzling. I just want to be.” His eclectic farewell setlist was as defiant as the artist himself.

Mid-career, Mos Def might’ve seemed hiphop-disillusioned and Hollywood-bedazzled, with roles in The Italian Job, Be Kind Rewind, Cadillac Records (playing Chuck Berry), and others. His heartfelt NYC farewell shows seemed bittersweet, not only because of his slow fade to black, but also because — a bit like his career — they didn’t quite measure up to what fans who loved him expected. With his political consciousness, lyrical dexterity, and acting chops dating back to the 1988 TV movie God Bless the Child, he could easily have been more Kanye-ubiquitous on the pop landscape. However unfair, it’s easy to embrace the feeling instead that, in his way, in the end, he kind of gave up. Framed in hiphop historical perspective, a short-lived, Jay Z–like retirement would surprise no one. But considering what’s become of ‘Ye, maybe Yasiin had the right idea.