Rick Famuyiwa’s sly coming-of-age comedy Dope opens with an onscreen dictionary definition of its multivalent title. Depending on the context, dope can be an illegal substance sold as a street drug; a person who acts in a foolhardy manner; or a term of praise in black American slang, signifying the coolness of the person or thing so designated. All three meanings work in tandem in Dope, a movie about a black teenager who foolishly gets mixed up in the sale of an illegal street substance, then winds up discovering inner reserves of cool he never knew he possessed.

Malcolm Adekanbi (Shameik Moore) is a high school senior living with his single mom (Kimberly Elise) in the Bottoms, a gang-controlled neighborhood in the L.A.-adjacent city of Inglewood. Along with his geeky best buds, scrawny Jib (Tony Revolori, familiar from his role as Zero the lobby boy in Wes Anderson’s Grand Budapest Hotel) and butch Diggy (Kiersey Clemons)—who dresses so much like a boy, she’s generally presumed to be one—Malcolm pursues a set of interests that are, to say the least, not widespread among the kids at his tough urban high school: videocassette tapes of 20-year-old Yo! MTV Raps episodes. Punk rock, which he writes and plays in a band called Awreeoh (say it out loud) with Diggy and Jib. Malcolm even sports an old-school flat-top haircut and brightly patterned button-down shirts, earning him the nickname “Fresh Prince” from the school’s pack of bullies, who regularly hunt him down in the halls to divest him of his vintage sneakers.

Malcolm is a good student who’s just trying to keep his nose clean until he can get out of the Bottoms and into Harvard (though the school’s placement counselor warns him he may be setting his sights a little high). But in the last weeks of senior year, he and his buddies get embroiled in a sketchy deal that could turn into an entrepreneurial opportunity—shades of Risky Business, a film Famuyiwa has cited as a direct influence. On a whim the three friends crash a wild birthday party for the corner drug dealer, Dom (played by the rapper A$AP Rocky in a performance that lets the character’s vulnerability peek out from beneath the swag.) The police raid the event, and Jib, Diggy, and Malcolm take off in different directions. But the next morning at school, Malcolm realizes that someone has stashed a hefty supply of the club drug molly, along with a loaded handgun, in his nerdy camouflage backpack.

All Malcolm wants is to get these dangerous items back in the hands of whomever they belong to as quickly as possible. But that proves to be more difficult than expected. Dom is now in jail, and the guy making threatening calls to Malcolm’s phone may be an FDA agent, or he may be the dangerous head of a rival gang. At Dom’s behest, Malcolm and his friends attempt to deliver the stash to the fancy house of a local kingpin. But the only people home are the gangster’s two spoiled kids, would-be rap producer Jaleel (Quincy Brown) and his bored, horny sister, Lily (the model Chanel Iman). A couple of very weird hours later, Malcolm, still in possession of the contraband-stuffed backpack, finds himself speeding to his Harvard alumni interview with a half-naked, stoned-out-of-her-mind Lily at the wheel, while his friends dodge gang-war gunfire at a nearby fast-food joint.

The second half of Dope loses some of the opening’s agreeably daft momentum, as the easy camaraderie among its charmingly geeky central trio is undercut by the stoner Burning Man type (Blake Anderson) they enlist to help them market the drugs on the “dark Web.” Malcolm’s on-again, off-again flirtation with Dom’s sometime girlfriend (Zoë Kravitz) never quite rises above the level of obligatory plot contrivance. And the scenes with the black Harvard alumnus assigned to vet Malcolm (Roger Guenveur Smith) are a little blunt in pointing up the ironic similarities between Ivy League meritocracy and the ruthless capitalism of the drug trade.

But Dope’s biggest strength lies in its affectionate and honest portrait of a different kind of young urban blackness than we’re used to seeing on movie screens. In a flashback early in the film, the young Malcolm opens the only gift he ever received from his long-absent Nigerian father—a VHS copy of the movie Superfly, identified in an accompanying note as the dad’s favorite movie. In its subject matter, Dope has a lot in common with that blaxploitation classic—both lead the viewer on a perilous trip through the underworld, accompanied by super-fly music. (Pharrell Williams wrote Awreeoh’s original songs in Dope; the soundtrack also pulses with great early-’90s hip-hop from groups like Digital Underground and A Tribe Called Quest.) But rather than glamorizing the ineffable cool of its hero, Dope insists on showing us the fragility and uncertainty that underlie Malcolm’s construction of his still-evolving self amid the ever-present threat of danger in his city.

In the college application essay that Malcolm struggles to complete between police raids and black-market drug negotiations, he paints contrasting pictures of two very different candidates. One is a high-achieving, Ivy League–bound black nerd, the other a stereotypical fatherless ghetto kid who sells drugs, carries a gun, and mixes with the wrong sort. It isn’t just college admissions committees who too often draw a bright line between those two types of young black man, assigning cultural value to one and dismissing the other as a lost cause—it’s cops, teachers, juries, ordinary citizens, and Hollywood movie audiences. Thanks to a witty, fast-moving script (also by Famuyiwa) and a sensitive performance from the newcomer Moore, Dope helps us see how a young black man coming of age in America faces complications unforeseen by the smugly entitled high schooler played by Tom Cruise all those years ago in Risky Business. Sometimes you do just have to say “What the fuck?” and make your move—but business gets a lot riskier when whatever move you make can end up getting you shot.