Toward the end of The Last Samurai, Helen DeWitt’s 2000 novel about a single mother and son bouncing around the poverty line as the latter searches for a suitable father figure, that son has a conversation with a brilliant but difficult pianist. “Why don’t you make a CD?” the son asks. The pianist replies: “No one would buy the kind of thing I’d like to put on a CD and I can’t afford to make a CD that no one will buy.” The Last Samurai is hailed by critics and sold well over 100,000 copies. But due to contract math that would make Q-Tip blush, DeWitt ended up owing her publisher money. Before long, the book fell out of print. In the decades since, DeWitt’s fiction has focused on the material lives of artists as they struggle to navigate capitalism and psychological collapse.

Once an ascendant pop star and critical darling with a seemingly clean trajectory, Lupe Fiasco has seen his career has grow similarly tangled in the last 15 years. Since the public feud between him and his former label, Atlantic, over his third album, 2011’s Lasers, Lupe has remained nearly A-list by reputation, but with plummeting chart positions that suggest an audience segmented from the rap mainstream. He’s spoken frequently and eloquently about not only the business minutiae that has complicated his decision-making, but the ways hip-hop—and music writ large—is devalued compared to so-called fine art. (“If I want to read the next book by Helen DeWitt, I can just write it, and read it, and then write another one,” the Last Samurai author told The Believer in 2012. “Painters do that and nobody objects.”)

Samurai, which arrives almost two years to the day after Lupe’s eighth album, Drill Music in Zion, has plenty in common with that project: It’s produced entirely by longtime collaborator Soundtrakk, skews jazzy and subdued, and is slight (even slighter, in fact, at just 30 minutes). Its title was inspired by a moment in Asif Kapadia’s 2015 Amy Winehouse documentary in which the late singer leaves a voice message for producer Salaam Remi describing herself as a samurai battle rapper. For Lupe, the metaphor seems tidy: a motivated master working in relative isolation, honing a blade.

The album is conspicuously breezy. Lupe’s singing voice, a staple of his style as far back as The Cool, has only grown more pliable: See the way he moves between cadences and harmonies on the hook and verses of “Palaces,” each smartly shaped and carefully rendered. Elsewhere he flits, without apparent effort, between other modes of technical wizardry, like the staccato syllable latticework that dresses up pedestrian writing on the second verse of “No. 1 Headband” or the passage on “Mumble Rap” that begins with the line, “With a style similar to riding around looking for an arrest to resist.” It feels as if there’s some great, centrifugal force pushing down on the middle of each bar.

And yet this musical ease seems at deliberate odds with the torture Lupe describes, in first- and third-person, of trying to hack a career in the arts. There are the shows where the “front row the only row” (“Bigfoot”); there is the line on “Outside” where he says, “My business bone is connected to my ethics”—defiant from one angle, quixotic from another. Lupe lapses in and out of Amy Winehouse portraiture, and when he raps, on closer “Til Eternity,” about a beehive that “survived in a wreck,” it’s both a reference to her signature hairstyle and a metaphor that echos the ones he introduces earlier on the album. “We think we’re fortresses, made of stone,” he croons on “Palaces,” “but we’re just palaces made out of flesh and bone.” Despite the loftiness of “palace,” he presents this fragility without romance—or at least, with full knowledge of the forces conspiring to puncture it at every pass.