It's the night before Christmas and all through Wichita, mob-connected lawyer Charlie Arglist (Cusack) is making all the wrong moves. He's too generous while picking up expenses for overworked strippers, and too eager to do a good deed for the strip club's sultry operator (Nielsen).
Worse, Charlie breaks a mutually agreed-upon rule not to be seen in public with local porn impresario Vic Cavanaugh (Thornton). It's not that either man is ashamed to be spotted with the other. It's just that, well, the two guys have just ripped off $2 million "and some change" from the mob to which Charlie is connected. And it's probably not a good idea for them to appear too friendly, too conspicuously, before they can quietly depart from Kansas with their ill-gotten gain.
Of course, it's definitely a bad idea for Charlie to start behaving like a guy who's enjoying a few last laughs before leaving town. One thing leads to another, and the increasingly rattled lawyer finds himself ever more stressed by close encounters with a boozy business associate (Oliver Platt), a much too helpful cop (T.J. Jagodowski) and a burly mob enforcer (Mike Starr) with a frightful lack of holiday spirit. Ho, ho, ho? No way.
Charlie lurches through his long night's journey toward a grimly gray dawn in this gleefully nasty neo-noir dramedy set in a winter wonderland of amoral sleaziness. Director Ramis takes a darkly comical and sometimes savagely sardonic approach to hard-boiled pulp conventions. But the characters remain deadly serious—even while spewing foul-mouthed wisecracks—as they're beset by betrayals, triple-crosses and out-of-left-field happenstances.
Time and again, scriptwriters Richard Russo and Robert Benton (working from a novel by Scott Phillips) set you up for a predictably cynical payoff, only to spring something even more outrageous (and therefore all the more satisfying) as the ironies accumulate and the body count mounts. It's hard to be more specific about the plot or appreciative of the performances without spoiling one or two of the clever curveball twists. Suffice it to say that in this snow-blanketed corner of the lower depths, causing grievous bodily harm can sometimes qualify as a random act of kindness, and getting away with murder is a simple matter of great timing and dumb luck.