For almost 20 years now, Nike has asked young patients at the OHSU Doernbecher Children’s Hospital in Portland to design shoes. Jordans, Foamposites, what have you. These are snatched up by sneaker collectors across the world, including at an unveiling auction where one-of-one versions yield millions of dollars for the hospital. AirMax Zeros, VaporMaxs. They’re commodities, like anything else, but they turn the kids, many of them gravely ill, into spokespeople.

About halfway through Ajai, the absurdly detailed new album from the Chicago rapper Serengeti, the titular character is making small talk at a Congressional Black Caucus dinner. He’s there with his wife, a prominent medical professional, and so he’s seated next to doctors; one explains “the reduction of drug costs making it mandatory for federally qualified health centers to accept Medicaid.” Ajai doesn’t respond directly. He unlocks his phone, scrolls over to a photo of the Doernbecher 8s, and asks a simple question: “Have you ever won a shoe lottery?”

Over the last 20 years—roughly the same span as the Doernbecher program—Serengeti has made some of the most exhilaratingly strange records in rap’s underground. He’s like a ventriloquist with a deep Rolodex and deeper depression, a web of grand declarations and muttered asides sprawled across dozens of albums and EPs. Ajai is one of his most sharply drawn figures yet: a young Indian man obsessed with exclusive drops and merch collabs, who sets multiple alarms to wade through webpages or go stand in line and cop multiples if they have them.

From the beginning, Ajai makes plain his rationale: “Clothes is just clothes, I like the way that I look/I like the people in line, I like the effort it took.” But a dark undercurrent runs underneath. When he and his wife go on vacation (“Walking down the streets in Paris/It’s autumn here, and I’m in Supreme”), Ajai leaves her at a table so he can flee the restaurant and offer a passerby cold hard Euros for his stained sneakers; he returns during dessert and asks if she’d like to go shop for enzyme cleaners. At other points, Ajai’s wife cries from the other side of a bathroom door as her husband risks missing their flight to Cleveland (“You look fine, Ajai”); she begs him not to wear a certain suit to a work function; she drives him wordlessly home from a company softball game, where he has embarrassed both of them, Ajai “deeply nodding his head” to SWV while he bares his gold teeth––surely expensive.

Ajai’s story is confined to the record’s front half. This enforced brevity is an excuse to showcase Serengeti’s masterful storytelling: The fourth song is called, simply, “Summary,” and chronicles Ajai’s short-lived stint as a tutor to four Chinese boys, who are enamored with his tales of street life (Ajai “once did an overnight stay at a jail due to a clerical error”) and whose angry father soon forbids the relationship. He challenges Ajai to a fight, only for Ajai’s neighbor, a fireman, to step in as a proxy and be “savagely and entertainingly beaten” on camera, and lose his “beautiful wife, the Estonian” to the Chinese father. In the middle of all this, Ajai goes to therapy; he asks his therapist about the first time she saw the Balenciaga Triple S trainer. “She starts talking about self-esteem,” Serengeti raps, “but he’s distracted by her boring chair.”

On the B-side of Ajai, Serengeti returns to his most famous character, a semi-retired white rapper named Kenny Dennis, who’s beefed with Shaq, vehemently defended Steve Bartman, fallen in love with the late actor Brian Dennehy’s work, pined after a wife he believes was stolen by Tom Selleck, and suffered at least one psychotic break. When we re-meet Kenny during Ajai, he’s moved to Minneapolis and is working at a breakfast truck near an I-94 overpass. The album moves inevitably toward the point where Kenny has something Ajai wants to buy, but the transactional specifics are far less important than the baggage each man brings to the bargaining emails. As Kenny Dennis, Serengeti raps in a thick Chicagoland accent; the Ajai half serves as a counterpoint, revealing just how dexterous a rapper and vocalist Geti can be.

These halves are stitched together by the veteran Los Angeles producer Kenny Segal. After a formative period working with esteemed Angeleno rappers, including members of Freestyle Fellowship, Segal has of late taken to crafting full albums for some of rap’s most distinct voices. Over the last year alone, he’s helmed growling, stuttering LPs for R.A.P. Ferreira and billy woods. His beats here skitter from playful piano loops to claustrophobic fits: see “Don’t Wear That Suit Ajai,” which feels, unnervingly, like early RZA on less dust and more coffee.

The point here is not that “consumerism is bad,” or that you might get scammed trying to buy the Virgil/IKEA collab rug (“about six and a half feet,” Geti notes, recommending it for concrete or marble floors). Ajai is done in by his compulsions, his tunnel vision––not a ruinous Supreme drop. To hear him tell it, each long line or digital waiting room is its own Everest, and that rapid, dizzying ascent is worth the thousands of dollars and crying wives left in its wake.

The world rendered on Ajai can seem silly: exclusive honey to buy in bulk, Travis Scott socks on auction blocks, “rich Kuwaiti kids” who might drop so much money on your work uniform that you can retire early, American kids running up to middle-aged men promising thousands of dollars if they’ll sell their shoes off on the spot, the Grey Poupon ads as an emotional touchstone, the word “Balenciaga” as an ancient, guttural chant, the promise that branded goods shuffled by UPS from point to point can save us all. This world, of course, is our own.