"Millennial" is one of those terms whose definition was nebulous even before it reached a supersaturation point in the culture—feel free to file it alongside "indie" and "hipster" in that regard—but if there’s any one artist who grasps its spirit, it’s Makonnen Sheran, the singer and rapper who records as iLoveMakonnen. His label boss Drake is more successful and more readily meme-able, and there are plenty of rappers who are younger and/or more stereotypically "youthful," but no one can match Makonnen’s omnivorousness, his openness, his sense of possibility. He’s a product of the Internet and incredible tragedy: A witness to the accidental death of his best friend at age 18, he spent seven years bouncing between jail, house arrest, and probationary purgatory. The online world served as a safe haven, a place for therapy and creative expression. He posted songs on Myspace, interviewed musicians and businesspeople on his personal blog, wrote and sang and drew and designed. His probation finally ended in May 2014; three months later, the most popular rapper in the world had hopped onto one of his songs.

Perhaps it’s easy for young people to see themselves in Makonnen because many of them grew up spending their nights the same way: devouring every bit of culture in sight whether it’s the Killers’ greatest hits or old episodes of "Dragon Ball Z", drowning themselves in tabs they never get around to reading. A few clicks away from some kind of fame, whether it’s 15 minutes on Twitter or a top 15 hit on the Billboard charts: that’s life if you came of age on the Internet, and Makonnen’s no different.

That’s not to suggest that "Tuesday" was a fluke, or a product of sheer coincidence rather than talent or hard work. It became a hit because of Makonnen’s genial nature, his oddball charisma, and his ability to craft a perfect, simple hook, something that stood out even when he was churning out Bandcamp tapes of basement pop that sounded more like Ariel Pink than anything out of OVO’s shadowy, hyper-lean catalogue. You can hear it in the early versions of songs like "I Don’t Sell Molly No More" and "Whip It", in arrangements that are raw but ooze melody. Self-produced until 2013, his work took an immediate leap forward when he began working with outside producers on 2014 mixtape Drink More Water 4. Played against strange, vaguely gothic beats with real momentum and heft rather than the plinky, tinny sounds of his keyboard, Makonnen's own strangeness and versatility was amplified: his workmanlike relationship with drugs and alcohol, his wobbly vocal takes, the way he doodles arrhythmically like a kid coloring with the wrong hand. The iLoveMakonnen EP, released later that year (and again, with a slightly adjusted tracklist, a little later still), took that new formula and refined it further.

Drink More Water 5 is the first tape he's released since "Tuesday" rocketed him to minor fame, and so it's unsurprising that it's starrier and more polished than anything else in the series. But it also serves to illustrate a point you could've made at any point in the last few years: Makonnen songs are inherently risky propositions, destined to become impossibly sticky earworms or blatant failures with no intermediate outcomes in sight. Put another way, he's not interested in hitting singles or doubles: every swing is either a home run or a flagrant, wild strikeout. In "Tuesday" and "I Don't Sell Molly No More"—and his verse on Father's louche breakout single "Look at Wrist", a sing-song transmission from another dimension—he managed the former, and DMW5 has a few of its own, particularly the songs that feature other, more conventional rappers.

In the same way Makonnen took a step forward when he emerged from his DIY cocoon to work with other producers, he's a powerful complementary force, whether he's singing hooks or delivering verses alongside rappers who are tonally different. On the remixed version of "Whip It", he's a welcome burst of color against the hyperkinetic human fireworks of Migos; on "No Ma'am" and the remix of his earlier "Dodging 12", his melancholy spills over the edges of harder-edged, more aggressive drug rapping.

Songs like this are exceptions to the rule on DMW5. Much of the tape's remainder—and the solo Makonnen tracks in particular—are almost tuneless, sketches that are shroomy and distant rather than focused and catchy. Some, like the dewy "Super Clean" or "Other Guys", sound like they bubbled up from the minds of producers like James Ferraro or Daniel Lopatin c. Replica; others still, like stark confessional "Get Loose With Me", are an inch away from the blue, piano-pounding work of Spencer Krug's Moonface. Makonnen is not a particularly skillful singer or lyricist, so these songs are dependent on qualities that are a little more unpredictable or intangible: emotional rawness, amateurish intimacy, a stray line or melodic phrase happening to click into place.

Beyond its value as a standalone release, DMW5 invites larger questions about Makonnen's future as a mainstream star and the cap on his commercial potential. He's planning to release his major label debut later this year, and as the first member of OVO to come from outside of Drake's Toronto cabal, there's a lot of hope being placed on his ability to keep cobbling hooks together, like someone taking handfuls of spare parts and building capable sedans out of them. Can he crack down and deliver an album chock-full of heat rocks like "Tuesday"? It's within the realm of possibility.

But it seems much more likely that he'll follow in the footsteps of his greatest influence, the BasedGod: operating from the periphery, prolific and defiant, largely unconcerned with structure or melody or convention, opening doors for contemporaries who are more focused and/or traditionally skilled. (These doors don't have to be musical, either; consider Makonnen's fluid, nuanced response to questions about his sexuality in this New York Times profile.) In the meantime we're left with tapes like this, floating in the ether, being asked to accomplish things their creator doesn't seem all that interested in pursuing.