It's Christmas Eve in Wichita Falls and the weather and roads look dicey as an ice storm is moving in. Nevertheless, that doesn't deter mob lawyer Charlie Arglist (JOHN CUSACK) and his partner Vic Cavanaugh (BILLY BOB THORNTON) from stealing more than $2 million dollars from mob boss Bill Guerrard (RANDY QUAID).
Charlie actually does the deed and is the nervous one, especially since he's heard that Guerrard's thug, Roy Gelles (MIKE STARR), is looking for him. Vic, on the other hand, is nothing but confident and tells Charlie to be cool for a few hours and they'll then be home free. But Charlie has a hard time doing that, especially since he can't keep his eyes off the alluring Renata (CONNIE NIELSEN) or that his best friend, Pete Van Heuten (OLIVER PLATT) drunkenly (and loudly) tells everyone that Charlie's a mob lawyer.
As the evening wears on and Roy eventually shows up, the duo's plan takes unexpected turns as things become just as slippery for them as the icy streets outside.