28. Serengeti, 'Kenny Dennis III'
Wise words from Kenny Dennis: "You've got to bet big. Win big. Lose big. No even stevens." Few creative gambles come more risky than the high-concept Kenny Dennis saga, now three records and an EP, in which Chicago indie-rapper Serengeti plays a middle-aged, blue-collar ex-rapper into the Bears, Tom Berenger and Benzedrine. The jokes grow more insular with every plot twist as he raps with a Great Lakes accent as thick as his mustache. On Kenny Dennis III, our hero forms hip-house candy-rap group Perfecto with his old pal Ders (played by Anders Holms of Workaholics). They tour Midwestern malls, squabble in drive-thru parking lots and generally "have a time." What makes it special is that, somehow, Seregenti infuses the Adult Swim off-brand jokes with ineradicable sadness — the slow fade of time's passage, the desire to recreate one's youth, the impulse to go hard and potentially cash out one last time. J.W.