David Cohn's earned a reputation as a storyteller who can dredge up some pinpoint details and harrowing emotions in his more serious releases as Serengeti. And since Kenny Dennis first bellowed his way into the world, an alter ego that first seemed like a delivery means for some oddball Chicagoland Joe-sixpack comedy has become the sort of deeply familiar character that reveals new facets each time out. Increasingly less of a pure comedy character as time goes on, the raspy, mustachioed Cool Uncle of indie rap has also turned out to be a put-upon underdog, a proud yet self-conscious working artist who's determined to shake off failure at all costs with a strident determination. In hindsight, his defense of Cubs scapegoat Steve Bartman feels like a strong solidarity with a guy who has to live with the weight of a "What Could've Been?" scenario that was actually out of his control.

Kenny Dennis III is technically a few Roman numerals behind the actual size of the Dennis discography (word to Tha Grimm Teachaz). But it does make for a strong thematic trilogy with 2012 character-study Kenny Dennis EP and last year's pathos-injected Kenny Dennis LP. Odd Nosdam returns to provide more off-kilter, goofy yet stirring production, and there's another suite of skits featuring Anders Holm from "Workaholics" playing Kenny's on-again/off-again estranged friend Ders. But this time, there's a stronger throughline to the concept: most of the feel to Kenny Dennis III hinges on what happens when Ders decides to move back to Chicago from L.A. and tries getting a hip-hop group going with Kenny. It all goes to hell pretty quickly over the course of two separate skit medleys, as Kenny's big idea to record '90s throwback freestyle house crossover as "Perfecto" brings out the worst in Kenny's ego and puts another wedge between himself and Ders. As off-the-wall nonsense goes, it's actually pretty affecting, a mixture of caricatured absurdity and real-folks groundedness worthy of Prince Paul.

But the frustration and the anger are also a little more palpable than on LP and EP, with Ders' POV of Kenny's jerk-ass behavior on tour offset by Kenny's own diatribe-flow stories. He still liberally sprinkles in references to sports fandom, '80s muscle cars, and basic-cable action movies, but now it feels more like those points of interest double as security blankets. "No Beginner" plants his feet firmly on the ground in opposition to calculated trendy weirdness -- "I'm not tryin to kill turtles or dye my hair strange colors/ I'm just tryin' to do rap songs and be down with my brothers"—but a daily diet of "hot dog for lunch/ hot dog for dinner/ don't eat breakfast/ I am no beginner" isn't exactly the glamorous life. He gets into chest-puffing brawls in "Shidoshi" over people mad about how he's "makin' it look good," attempting to pull Dim Mak death punches on fools. (The video for this track, meanwhile, involves a failed intervention.) On "Buddy Guy", the Chess Records legend's name becomes a taunting way of addressing a hopped-up adversary who might just be himself. And "Tanya T" is the flashpoint where things implode, as Kenny helps bail out his little brother—a victim of domestic violence—and puts a (garage) roof over his head, only to see him become a police informant. When the track ends with Kenny screaming "and this the thanks I get?!" over and over, any impressions of Kenny Dennis III as "comedy rap" dissipate pretty quickly, and it's hard not to feel for a guy once easily thought of as a funny voice and funnier mustache.

Serengeti inhabits the Kenny Dennis world so thoroughly that the affectations and tics have become a style to actually contend with, raspy muttering and roaring bellows concealing vivid free-association worldbuilding and playing with the joys of repetition. The characteristic Odd Nosdam production toes that line between awkward, whimsical discomfort and melancholy, muddy stoner soul, a Madlib/Black Moth Super Rainbow midpoint that flips from amusing to unnerving without you even noticing. And in the end, all the blue-collar detritus and supposed punchlines give a stark portrait of a man who invokes his '90s glory days like a shield against their loss, making a clear point of the coping-mechanism properties of his nostalgia without either reveling in it or mocking it. "Sometimes I watch The Negotiator and think about life's long times," he admits in the midst of the downcast, reflective closer "Tickled Pink", a search for perspective and meaning in a life that might not have turned out the way he wanted it to.