Plot
Ray Hughes (Hines) and Danny Costanzo (Crystal) are two detectives working Chicago's North Side, known for their childish demeanors and unorthodox police methods, which get results in their various cases. One such case involves trying to bust up and coming drug dealer Julio Gonzales (Jimmy Smits). After arresting Snake (Joe Pantoliano), one of Julio’s associates, they convince him to wear a wire in order to get the necessary evidence to put Julio away. Snake is setting the detectives up, however, and during the bust, the pair look as though they will be killed for sure, but two undercover detectives in Julio’s gang step in to make the arrest. In the ensuing melee, most of Julio’s gang escape, but Ray and Danny capture Gonzales.
Back at the station Ray and Danny expect to be praised, but instead their captain (Dan Hedaya) chastises them for their sloppy work (as revealed by Snake’s wire) and orders them to take a vacation. On vacation in Key West, Florida, the pair begin to question their career choice after the experience and decide to retire and open a bar.
When they return to Chicago and inform the captain of their intentions, they find out that Gonzales has been released and is free on bail. Incensed, they vow to capture Gonzales before retiring, but by being a little more careful in the process. To add insult to injury, Captain Logan assigns them the additional task of training their replacements before they go; detectives Anthony Montoya (Jon Gries) and Frank Sigliano (Steven Bauer), none other than the two undercover officers that saved them from being killed in the Gonzales bust.
During one of the attempts to capture Gonzales, Ray and Danny confiscate a large shipment of his drugs coming from Colombia. In order to get them back, Gonzales kidnaps Danny’s ex-wife Anna (Darlanne Fluegel), whom he still loves and has been trying to reconcile with, and says he will trade her for his drugs, otherwise he will kill her. Danny agrees, leading to the final confrontation inside the high-rise atrium of the James R. Thompson Center. During the ensuing firefight, Danny and Ray ironically rescue their would-be protégés in a way similar to their own rescuing, and Gonzales is killed. Anna and Danny reconcile and he and Ray decide not to retire after all.
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