A consistently intelligent (or at least bright), coherently constructed comedy that is on occasion a rather pointed critique of the American education system in the…
It's a busy Christmas Eve for Charlie Arglist, who visits his former in-laws, steers his drunken buddy out of trouble, buys toys for his kids, waives the stage rental for a stripper at his topless club, and cheats, lies, steals and kills. Perhaps of all actors only John Cusack could play Charlie and still look relatively innocent by Christmas Day. He does look tired, however.
Charlie is a mob lawyer in Wichita, Kan. He is in fact the best mob lawyer in all of Kansas. We know this because his friend Pete (Oliver Platt) announces it loudly almost everywhere they go. "I wish you wouldn't do that," Charlie says, but Pete is beyond discretion. Pete is married to Charlie's former wife and has inherited Charlie's former in-laws, a circumstance that inspires in Charlie not jealousy but sympathy. They are fascinated that the woman they have both married is the only adult they know who still sleeps in flannel jammies with sewn-on booties.
Charlie's holiday has begun promisingly. He and his associate Vic (Billy Bob Thornton) have stolen $2.2 million belonging to Bill Guerrard (Randy Quaid), the local mob boss. They think they can get away with this. They certainly hope so, anyway, for as Charlie tells Vic, "I sue people for a living. You sell pornography. Bill Guerrard kills people." Charlie also manages a topless bar and is attracted to its manager, Renata (Connie Nielsen), who has suggested that Charlie's Christmas stocking will be filled with more than apples and acorns if certain conditions are met.
It is all very complicated. There is the matter of the photograph showing a local councilman in a compromising position with Renata. The problem of Roy Gelles (Mike Starr), a hit man for Bill Guerrard, who has been asking around town for Charlie, probably not to deliver his Christmas bonus. The question of whether good old Vic can be trusted. And the continuing problem of what to do with Pete, who is very drunk and threatens a dinner party with a turkey leg, which in his condition is a more dangerous weapon than a handgun.