At mid-afternoon on Christmas Eve in Wichita, Kansas, mob lawyer Charlie Arglist (John Cusack) and crooked businessman and pornographer Vic Cavanaugh (Billy Bob Thornton) steal over $2 million from their mob boss Bill Guerrard (Randy Quaid). While it appears, there will be an easy getaway for the pair, they learn the roads out of town are too icy to drive on. Vic takes the cash for safe-keeping, and they split up and try their best to evade being captured by Guerrard and his men, who have discovered their scheme. Charlie visits Sweet Cage, a local strip-club, owned by Renata Crest (Connie Nielsen), a woman whom Charlie has long lusted for. She is upset because a new law will prevent strip clubs from operating after the first of the year. In response to Charlie's persistent efforts, she tasks him with bring her an existing compromising picture, taken of a local crusading politician, so that she can use it to blackmail him to keep her club in business. She hints that she might respond favorably to Charlie's sexual desire if he helps her with this. Before he leaves the club, Charlie sees someone looking for him. He hides in the bathroom, where "As Wichita Falls, So Falls Wichita Falls" is written on the walls. He manages to evade the hulking man because Sidney the bartender lies and tells him that Charlie already left. Once the man leaves, a panicked Charlie calls Vic to warn him, but Vic dismisses his concerns. Charlie drives to another strip club owned by Guerrard and removes the photo from the backroom safe. Before he gets there, his car skids on ice and he is stopped by Officer Tyler, who asks Charlie to remember him to his boss, Guerrard. Charlie promises to do so, but then can't remember the man's name a minute later. At the second club, he is unexpectedly nice to a stripper, and the bartender there takes note of that. While Charlie is in the back stealing the photograph, the menacing man shows up again, once again demanding to know if Charlie has been there. Once again, the bartender lies for Charlie and he's again able to evade capture. Once he leaves, a now very panicked Charlie rushes out with his phone open to call Vic again but slips on the ice and breaks his phone. Charlie drives to a restaurant to meet with Vic in person instead, and Vic assures him things will be okay. While they're talking, Vic gets a phone call from someone and tells Charlie it's his overweight wife asking when he'll be home. Vic leaves, but before Charlie can go, the bar manager asks Charlie to take care of Pete (Oliver Platt), Charlie's old and now very drunk friend. Pete is married to Charlie's beautiful ex-wife Sarabeth. Charlie takes Pete to the home of Pete's current and Charlie's ex-in-laws where his children and Sarabeth are having dinner with her parents. It's clear that Pete doesn't want to go in and is unhappy with his new marriage to Charlie's ex-wife. While still outside the house, he drunkenly confesses to Charlie that he and Sarabeth were constantly "f**king everywhere" while she was still married to Charlie. Pete asks Charlie if that makes him angry, and Charlies replies, "Actually, it makes me curious. Makes me wonder who she's f**king now." Once inside, Pete acts out, cursing and saying terrible things about both his wife and his in-laws. Charlie attempts to talk to his children but is met with open hostility from his older son for not being more involved in their lives. Finally, Sarabeth's mother tells him to leave, and take Pete with him. So, Pete and Charlie go back to the restaurant they'd left earlier, and ask the bartender for one more drink. She agrees to give them each one for free if they will drink it and then leave. Charlie calls the Sweet Cage looking for Renata while Pete makes drunken sexual comments to the bartender, despite the fact that her boyfriend is waiting there for her close. The boyfriend eventually throws him out of the restaurant and then kicks him in the scrotum. Pete vomits in Charlie's car, Officer Tyler shows up again, and Charlie drives Pete home (which was previously Charlie's house), where Pete passes out. Charlie "borrows" Sarabeth's new Mercedes (which was a gift from Pete) from the garage since Pete threw up all over Charlie's car. Charlie goes back to Sweet Cage to find Sidney the bartender beating up a guitar player. Renata has returned, so he gives her the photo. Based on Charlie's kindness to the stripper at the other club and his refusal to demand anything in return for the valuable photo, Renata deduces that Charlie is hiding something. He hints at the existence of money, and she suggests they go off together. Before they can do that, however, she tells him that Vic had called her earlier to say Charlie had been right about mob enforcer Roy Gelles (Mike Starr) looking for the two of them, and that Charlie needs to go meet with Vic at The Velvet Touch while she closes her bar. Charlie goes to The Velvet Touch and finds a severed human thumb in the back room. He drives to a bridge to be sick, and is once again spotted by Officer Tyler, whose name he still can't remember. He heads to Vic's house and sees a gun go off through the window. He breaks into the other car in Vic's driveway and finds ID belonging to Roy, so he assumes that Roy just killed Vic. He calls Renata to tell her so, and she encourages him to take Roy out and get the money from him so they can run off together. She encourages him to make this his "defining moment" to be "something more." Charlie goes into Vic's house, finds Vic's wife newly dead and is then startled by Vic himself. Vic tells him that Roy shot his wife, but that he managed to lock Roy up in a trunk. After an argument about which car would hold the two bodies best, the two of them stuff the trunk with Roy inside it into the back seat of Sarabeth's Mercedes, and the corpse of Vic's wives into the trunk, then head for a local lake. On the way, Roy continues talking to the two of them, telling Charlie Vic killed his own wife, and that he's going to kill Charlie too. Vic berates Charlie for "being nice" on Christmas Eve, saying it's a dead giveaway that he's planning to leave town, then gets annoyed with Roy's talking and shoots into the trunk, which becomes quiet. Charlie and Vic get the trunk down onto a dock at the lake, but it's shot open from the inside and Roy gets out, shooting Vic in the process. Vic shoots Roy dead, but then falls into the frozen lake. Vic begs for help, but Charlie realized that Roy was right, and Vic was planning to kill him once they got the bodies into the lake, and then take the money for himself. He dumps Vic's wife's body on Vic, telling him, "I don't want you to die alone," and leaves Vic to die, still pleading to be saved. But then Charlie discovers the carry-on bag in the car does not have the money in it, and that he doesn't know where the money actually is (and with Vic dead, has no way of figuring that out), so he gets drunk. He calls Renata and tells her what has happened, but she asks him to come to her despite not having the money. When Charlie hangs up the phone, it is revealed that someone is pointing a gun at her. First Charlie heads back to his old house and delivers some very cheap Christmas gifts to his children, leaving them under the tree. Pete is still passed out there and begs Charlie to take Pete with him when he leaves town. Returning to Sweet Cage, Charlie discovers Bill Guerrard's car in the parking lot. He goes inside just a moment when Guerrard is in the bathroom, to discover that Renata is tied to a chair. She has just enough time to tell him where a shotgun is hidden before Guerrard emerges from the bathroom, not seeing that Charlie has arrived. Charlie manages to fetch the double-barreled shotgun from behind the bar, and Guerrard discusses the situation with Renata, surmising it was really her who designed the plan, as Vic was too dumb and Charlie too cowardly to pull it off, without her encouragement. Charlie returns and points the gun at Guerrard, but Guerrard just taunts him. At Renata's urging, Charlie fires the gun, but it is loaded with bird-shot and only superficially wounds him. As Charlie starts to cut Renata loose, Charlie is stabbed in the foot by a recovered Guerrard. Officer Tyler, making his rounds, hears the gunshot and arrives but Guerrard shoots him dead. Renata frees herself and stabs Guerrard in the chest. A struggle ensues, and Charlie manages to kill Guerrard with a second shot to the back of the head at point blank range. Charlie mends his wound, while Renata cleans Guerrard's blood off of herself, and suddenly sees Vic's carry-on bag containing the money in her open closet. Flashing back, he realizes Renata is the one Vic was having dinner with earlier, and that he and Renata were planning to go off together after Vic had killed him. Renata emerges from the bathroom acting as if she is going to seduce Charlie. As they embrace, Charlie shoots Renata with Guerrad's gun just before she can kill him with a concealed razor she brought out of the bathroom. On Christmas morning, a sad Charlie drives out of town with the money. He finds Sidney with his kids on the side of the road in a camper-motor home, on their way to Six Flags. They are stalled because the camper has run out of gas. Charlie lets Sidney siphon some gas from his tank and Sidney tells him that Charlie's the nicest guy he knows. Charlie says he's "awfully sorry to hear that." They wish each other well, but as Sidney's motor won't immediately start. Before he drives off, Charlie pulls a red Sharpie from his pocket and begins to write "As Wichita Falls, So Falls Wichita Falls" on the back of the camper. Based on the handwriting and the ink color, it's implied that he was the one writing this phrase all over town the entire time. Not seeing Charlie back there, Sidney accidentally backs into him, knocking him to the ground. Charlie picks himself up and gets back in the Mercedes, where Pete is revealed to have been lying in the back seat the entire time. He has at last awoken from his stupor and wants to know where he is. Charlie tells him he's in Heaven. They wish each other "Merry Christmas" and drive off to a new and different future.
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