Actually, the stakes never feel high in first-time writer/director Hue Rhodes's listless drama about a reformed gambling addict (Steve Buscemi) still itching for scratch tickets. Not a man to mix with Sin City — yet that's exactly where Buscemi's milquetoast John Alighieri (Dante alert!) heads when he leaves behind his desk job and bosomy cubicle mate (Sarah Silverman) to investigate an insurance-fraud claim.
Manning the wheel of his descent into temptation: an insane, and perhaps crooked, colleague named Virgil (the unsung Romany Malco). At each increasingly bizarre pit stop, Rhodes stokes the "Inferno" metaphor (lots of fire, a thug dubbed Lou Cipher), but he never transcends self-conscious quirkiness.
And the indie trifecta of clunky voiceover, scrambled chronology, and dream sequences can't fatten the slight story. Pity there isn't more of Peter Dinklage as John's wormy supervisor. Given the dominant motif, he's the ultimate boss from Hell.