For generations, the archetypal New York City weed transaction went something like this: A nervous college kid wanders into Washington Square Park and, half a second later, meets a shady, unkempt dude in a poncho. A stale dimebag and a greasy bill are exchanged in a handshake. The student returns to his dorm, high-fives his roommate, puts on some Dead or Phish or Dave, and fires up a bong while the boys gaze at the Bob Marley tapestry on their wall.

If pop culture has begun to understand that the city’s marijuana trade rarely looks that way anymore, it’s thanks in part to “High Maintenance,” a big-hearted HBO dramedy about a weed delivery man. Co-creator Ben Sinclair stars as the Guy, an unnamed dealer whose tools of the trade include a bike, a smartphone, and a bartender’s unassuming amiability. His customers are beleaguered Airbnb hosts, lesbian activists, immigrant parents, social media influencers, artists, agoraphobics, and countless other New Yorkers of all races, genders, religions, and sexualities. The show’s music is just as diverse, avoiding stoner clichés like jam bands in favor of tracks that nod towards psychedelia or represent a cross-section of the city’s residents.

“High Maintenance” debuted, in 2012, as a low-budget web series whose three-episode first season ran roughly as long as a single network sitcom episode. Despite that initially modest scope, the show has had music supervisor Liz Fulton on staff since the beginning. In its brief, early vignettes, which usually introduce new clients, songs help to quickly establish characters. Episode three, “Jamie,” brings the Guy to the home of two white women who buy multiple varieties of olive oil, decorate with exotic houseplants, and crank up Bon Iver’s “Flume” to a deafening volume on laptop speakers. So, of course they’re the kind of gentle, privileged souls who’d buy weed just to get their dealer to come over and humanely get rid of a mouse in their apartment.

The HBO series, which ends its second season this Friday (March 23), takes a similar approach to matching songs and characters. Like the show and its unnamed hero, Fulton’s syncs are witty, empathetic, and observant, but never straight-up mean. A young aspiring writer in the season-one episode “Selfie” spends a day out in the city, Instagramming her food and outfits. Broke, idle, lonely, but desperate to project a hip, carefree image, she posts and “likes” her way through a montage set to U.S. Girls’ “Damn That Valley.” The song’s darkness lurks beneath the surface, with clanging percussion hidden under a dance beat and Meg Remy’s sugared vocals tipping over into delirium. In the scene, Remy’s repetition of the title calls to mind the uncanny valley, that sinking feeling you get when you encounter an artificial but realistic simulation of human life. The double entendre highlights the sadness of a character who might otherwise come across as just another image-obsessed millennial; “Damn That Valley” is a diagnosis more than a burn.

The show’s emotional intelligence goes hand in hand with its radical inclusiveness. In the Guy’s world, a father exasperated by his wife’s helicopter parenting, a black real-estate broker renting apartments to the yuppies gentrifying her old neighborhood, and a gay man driven mad by his bitchy female best friend all deserve to be understood. More importantly, none of the characters are defined solely by their identity markers. That fluidity comes through in the music, too, which tosses a staggering range of cultures, nationalities, and styles into its New York melting pot. A Muslim college student finds rooftop tranquility to the ambient sounds of Tycho and Ratatat. “Money Money Money…” by Colombia’s Bomba Estéreo plays as the Guy racks up sales after a traumatic event. And on a night that ends with a kiss between a teen girl and her mother’s female friend, a different young white girl raps along with “Ooouuu” by lesbian rapper Young M.A. “High Maintenance” has always felt like a kindred show to “Broad City” in some ways, but its enormous cast of characters makes its approach to music supervision feel more eclectic and organic.