The prevailing narrative of Chicago rap does not allow for an eccentric like Chris Crack. His music neither bears the whiff of patchouli of the influential YouMedia and Young Chicago Authors open mics, nor does it share the permanent gun-violence scarification of the erstwhile drill scene. It is not the pastel proselytizing of Chance the Rapper; it is not the thundering L-train rumble of G Herbo. (Certainly, it is not the stuttering, mid-life crisis of Chicago’s prodigal son and number-one Charlie Kirk fan, Kanye West.) In a city where other rappers tend to be painfully cloying or brutally blunt, he’s acerbic and salty. Crack makes elemental, soul-looping boom-bap for the late aughts—no Wild Style, just wild shit-talking. With Being Woke Ain’t Fun, his third project in four months, Crack is attempting to further carve out this niche, one punchline at a time.

Luckily for Crack, a number of fellow Chicago outcasts have joined in on his harangues. Ugly Boy Modeling, Gzus Piece, and MC Tree—with whom Crack has a pair of commendable EPs, TreeSwag and Tree + Crack—add bite, but it’s Vic Spencer who’s Crack’s most potent foil. Their albums together, Who the Fuck Is Chris Spencer?? and Blessed, have coincided with Crack’s artistic growth; he no longer runs roughshod over beats like a seven year-old riding a sugar high, and instead sits calm and measured in the pocket. On “Coochie Nectar” and “Plair, Nephew, Pleighboi,” Spencer’s gravely baritone and dyspeptic demeanor offer a counterpoint to Crack, who’s high-pitched and punchy. Spencer claims to be eating “quesadillas with your bitch”; Crack, after asking rhetorically whether the Feds are tapping his phone, answers, “Man, fuck them niggas.” They’re tremendous assholes together, like Statler and Waldorf, or Rick Mahorn and Bill Laimbeer, or Ernest Hemingway and a daiquiri.

Still, the album feels overburdened by guest features—not for their lack of quality but their frequency. Of Being Woke’s 11 songs, over half include other rappers. It seems less like a Chris Crack solo project than it does an inspired bullshit session at Crack’s house, scored by August Fanon’s production. It sounds spontaneous, but spontaneity doesn’t always equal unbridled brilliance.

With Being Woke Crack tries to tread a very thin line between remarkable productivity and rushed, slapdash workmanship. On occasion, his album lands on the wrong side of that divide. Crack is a markedly improved rapper from his early tapes, but he’s still mostly unconcerned with choruses or sequencing; depending on your tastes, two-minute bursts of rap are either pleasant little kernels or too-thin bits of nothing. (While I generally like them, the experience can leave me empty.) The album’s most glaring weakness, though, is the inertia and uniformity of many of Fanon’s instrumentals. His soul loops often lack the richness of their source material and, instead of building and releasing tension, they tend to float by like clouds of vapor. Fanon’s capable of getting it right—the cascading drums of “Explanation Kills Art” are exceptional—but his beats on Being Woke are not his finest.

For those curious about Crack, Being Woke Ain’t Fun is a fairly straightforward introduction to his solo milieu. It’s likely Crack’s best album to date but, given his recent efforts—May’s Let’s Just Be Friends and July’s This Will All Make Sense Later—it’s one he’s likely to surpass. Maybe now, after a summer of slick punchlines over soul samples, the narrative of Chicago rap will allow for an eccentric like him to flourish.