When channel ORANGE came out in July 2012, Frank Ocean was more a person of interest than anything else. His first mixtape, Nostalgia, Ultra, had made him an outlier in R&B: too subtle for the mainstream but too interested in convention to be considered alternative. You could hear Stevie Wonder and Curtis Mayfield, Outkast and Aaliyah. But you could also hear a distinct brain clicking at a new register. Where Drake and The Weeknd sang about emotional numbness, for example, Frank Ocean imagined dating a dental student with access to pills (“Novacane”)—a familiar trope presented in an idiosyncratic way. He wasn’t trying to break the form, he was trying to take it apart and show you how it worked. channel ORANGE was a more radical step. Musically, the palette was both broader and more fragmented, touching on lounge (“Super Rich Kids”), hip-hop (“Crack Rock”), ’60s soul-gospel (“Bad Religion”), and ’80s New Wave (“Lost”). Like Pharrell (who co-wrote “Sweet Life”), Ocean was a synthesist, the kind of post-genre roamer who could bring a range of disparate styles together into a seamless whole. But the heart of the album was its mood. Even in its straightforward moments (“Thinkin Bout You,” “Bad Religion”), channel ORANGE has an elusive, poetic quality, the sound of pop and R&B reframed as something inconclusive and experimental (“Sierra Leone,” “Pyramids”). His wit made him feel like an old jazz singer, but his disaffection was pure 21st century. Here are the records and artists that helped make the album a modern classic, plus the ones it in turn influenced.

There isn’t a lot on channel ORANGE that sounds like jazz per se: the chord changes on “Super Rich Kids” and “Sweet Life,” maybe, or the vocal delivery on “Crack Rock.” But as much as the album descends from R&B, its spirit is closer to a jazz standard: wise, bittersweet, warm but detached. Listen to “Crack Rock” (“Your family stopped inviting you to things”) or “Sweet Life” (“Why see the world when you’ve got the beach?”) and you can almost picture Ocean taking notes from the corner of the bar, the tableaux of human drama unfolding before him. It’s a quality you hear in singer-songwriters like Randy Newman and MCs like André 3000, too: songwriting not as reaction, but reflection. And if he seems unfazed by his surroundings, that’s just his weird expression of hope: Somehow, he knows we all pull through.

Part of what makes channel ORANGE striking is the way it balances realism with something more heightened. Take “Crack Rock,” which starts out as a portrait of addiction (“You don’t know how little you matter until you’re all alone in the middle of Arkansas”) and ends as a nightmarish indictment of policing in Black communities (“My brother get popped and don’t no one hear the sound”). The material is concrete, but Ocean moves through it like a dream: hazy, associative, nonlinear. As much as channel ORANGE owes to albums like Songs in the Key of Life and Curtis Mayfield’s There’s No Place Like America Today, it also belongs to a broader legacy of Black artists who mixed an acute social consciousness with music that felt exploratory and abstract: Nina Simone, Sly Stone’s There’s a Riot Goin’ On, Funkadelic. The lesson isn’t just that Black artists could be as experimental as their white peers, but that you didn’t have to leave the real world while doing it.

The story of channel ORANGE will always, in part, be the story of Frank Ocean coming out: a risk for any public figure, but a special one for an artist navigating the institutional homophobia of rap and R&B. But it’s also worth highlighting Ocean as part of a lineage of male artists—Black, white, or otherwise—who play against type more generally, from the falsetto-driven love letters of early doo-wop like The Orioles to the fragility Miles Davis lent ballads in the ’50s (a stark contrast to the lover-man muscle of someone like, say, Coleman Hawkins) to Morrissey and The Cure in the ’80s, whose artful self-consciousness was part of what made them punk. And while it’s tricky to attach his orientation to his art, it’s also easy to see how the mix of reticence and empathy that makes channel ORANGE powerful might be familiar to the LGBTQ+ experience: When sharing your feelings only makes your life harder, you learn to stand off to the side—a wallflower, the anti-glam. Of course, that’s also what makes his music feel like a bellwether to anyone raised on the internet: that weird mix of sincerity, sarcasm, apathy and idealism. He’s breaking code. But he’s not trying to make a thing out of it.

Asked how he categorized himself just after channel ORANGE came out, Frank Ocean said the thing about R&B is that it felt so racial. His collaborator Pharrell, for example, just called him a “singer-songwriter,” because that’s what he is. But the most interesting ones are always somehow what Duke Ellington described as “beyond category,” or at least renegotiating what those categories mean. Ocean’s ability to connect the dots of his various interests—R&B, hip-hop, ’70s singer-songwriters and psychedelia, the aesthetics of streetwear and visual design—didn’t just expand the field for young Black artists, but for anyone chafing at the confines of their box. You can see it in the not-so-rootsy roots music of Bon Iver or in someone like Clairo, whose style straddles aspects of the so-called alternative and mainstream in a way that basically negates either term. If the mood of channel ORANGE feels like a product of life online, its eclecticism is, too: With a century of recorded music at your fingertips, you might as well sniff around.

channel ORANGE came out at the beginning of a fertile period for R&B: SZA’s Ctrl, Solange’s A Seat at the Table, Noname’s Room 25—even Beyoncé’s BEYONCÉ, which Ocean had a writing credit on (for “Superhero”) felt relatively experimental for an artist so mainstream. The question isn’t whether R&B could be presented as art music, but whether you could make art music that still honored the traditions of R&B. Ocean never played it straight, of course, but some of the best moments on channel ORANGE were when you could hear the classics peeking out from underneath: the Motown of “Forrest Gump,” the gospel of “Bad Religion,” the Philly-style elegance of “Sweet Life”—music that made novel use of its influences while also providing grounding for Ocean’s more abstract side. Sometimes the best way to honor tradition is to expand on it.

There’s a word you don’t hear often that applies perfectly to channel ORANGE: anhedonia, or the inability to get pleasure from normally pleasurable things. In a way, you can connect the numbness of Ocean’s characters to a lot of modern hip-hop and R&B, from Drake and Kanye (808s & Heartbreak in particular) to Future and The Weeknd. But where his peers can seem angsty or dramatic, Ocean tends to play off his numbness with a shrug. It’s a quality that runs through a lot of contemporary pop, from the plush, druggy feel of Beach House to the muted romance of The xx: music that sublimates its strongest feelings in beauty, understatement, and the quest for chill vibes. To paraphrase Ocean’s collaborator André 3000, the only thing cooler than being cool is being ice cold.