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Dangerfield plays Jake Puloski, a comedic and friendly warden who runs a privately owned prison for white-collar criminals and less serious offenders. Trouble starts when Puloski's plans for renovating his rundown prison are ruined by his superior, Eli Rockwood (Randy Quaid), a greedy businessman who inherited the prison from his deceased parents, who rejects his budget request. Rockwood also informs Puloski that his contract will not be renewed, which means that Puloski will be forced to retire in two months. At the same time, Rockwood is in the midst of selling his company to the very wealthy Gloria Beaumont (Kirstie Alley).
Without the funds for a proper remodeling, Puloski decides to allow a group of prisoners, Mile-Away (Phil LaMarr), Next-Week (Paul Rodriguez), Jerk-Off (Marty Belafsky), and Ears (Joe Nipote), to leave the prison to burgle a sporting goods store owned by Rockwood (on the condition that they are "back by midnight" before the guard Smitty (Tony Cox) makes his rounds). The plan meets many surprises however, complicating Jake's plan, including excitable store clerk Lance (Kevin West) and a sadistic security guard (Gilbert Gottfried) with his vicious guard dog named Princess.
The four prisoners break into the store, distracting Princess with the prison's guard dog whom they had fed viagra to earlier that night, and make off with the stolen gym equipment, but on the way back to the prison one of their truck tires goes flat. Next-Week and Mile-Away try to fast-talk their way past Sheriff Jack Hubbard (Harland Williams), who it turns out is an old school chum of Mile-Away. Hubbard loans them his tire jack and, after picking up Ears and Jerk-Off from the side of the road, the four head back to the prison.
The next morning, the store security guard discovers that all the equipment has been stolen, and his beloved dog Princess was "a slut". Sheriff Hubbard inspects the crime scene, promising Rockwood that he will catch the culprits.
At the prison, the convicts are ecstatic with their new equipment and Jake feels very proud of himself. The burglars tell Jake that they think they should get the other items the prison needs by robbing the other stores owned by Rockwood in the area, justifying it because Rockwood had been fiddling with their budget in the first place. Jake agrees to the plan since he has only two months left of his contract. Ears, Jerk-Off, Mile-Away, and Next-Week rob Rockwood's other stores of their cash to pay for the renovations to the prison.
Jake throws a Valentine's dance, inviting the wives and girlfriends of the convicts, where Next-Week introduces his girlfriend (Lisa Arturo) and her friend Veronica (Yeardley Smith) to his cousin Carlos (Jsu Garcia). Veronica figures out that the convicts stole money from Rockwood to afford all the changes to the prison and Carlos has to kiss her to keep her quiet. Inside the dance, a riot breaks out due to another inmate stealing Jerk-Off's inflatable date.
At the police station, Sheriff Hubbard discovers that a shoe left by Jerk-Off earlier belongs to a prisoner uniform at Rockwood's prison. He visits Mile-Away and after a scene of interrogation Sheriff Hubbard leaves. Mile-Away warns Jake and tells him to spread the word that there will be no more burglary jobs. Rockwood, however, has other plans. Along with Sheriff Hubbard, he creates a trap for the burglars in the form of a big weekend sale. The convicts read about it and decide to pull one last job to have some cash for themselves once they re-enter society. But Carlos demands to be a part of the job because he had to kiss Veronica to keep her quiet, leaving Jerk-Off out.
At the store, Ears drills into the safe but Next-Week mistakenly leaves his cousin Carlos to roam. Carlos breaks into jewelry cases trying to take them but trips the alarm. Upon opening the safe, they find it is empty, then run outside and are caught by Sheriff Hubbard and the rest of the police department. Mile-Away escapes in the van to warn Jake. Mile-Away admits that they pulled one last job and Jake admits that Rockwood was firing him.
Jerk-Off and Mile-Away enter the sheriff's department disguised as guards and manage to free Ears, Carlos, and Next-Week, escaping in the prison van, and entering a high-speed chase with Mile-Away riding with Sheriff Hubbard chasing the other burglars.
Jake shows up at Rockwood's house trying to confess to the masterminding the burglaries but Rockwood decides to chase down the burglars himself. Rockwood grabs a gun and has Jake ride with him, who are joined by Mrs. Beaumont, who has an odd attraction to criminals and high speed chases.
The chase ends at the prison where Ears, Jerk-Off, Next-Week, and Carlos zoom through the gate pretending to be prison laundry returning. Rockwood follows them in and notices the changes to the prison and realizes Jake masterminded the robberies. Rockwood says he will turn Jake in until Mrs. Beaumont comes into the prison and tells Rockwood how much she loves how well he treats the prisoners. Mrs. Beaumont says after seeing how he runs his prisons she definitely wants to merge her company with his and have Jake oversee all the prisons. Jake agrees and tells his gang that they need to stop the robberies permanently.
A year later Jake narrates, saying he has retired. Carlos and Next-Week were released first and were greeted by their women Veronica and Next-Week's girlfriend. Ears was released and led a decent life until he cheated on a game show using his super hearing and won a million dollars. Jerk-Off was married to his inflatable girlfriend and started a family; they had an inflatable baby boy. Mile-Away became Sheriff Hubbard's deputy and they became a great crime fighting duo.
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