Jimmy Dworski (Belushi) is a convicted car thief and diehard Chicago Cubs fan who wins tickets to the World Series in a radio contest. Unfortunately, he still has a couple of days left to serve in prison, and the warden will not let him leave and come back. With the help of other inmates, Jimmy stages a riot so he can sneak out of prison to see the game. On the way, he finds the Filofax of Spencer Barnes (Grodin), an uptight advertising executive, and Jimmy takes on Barnes' identity, while the life of the real Spencer Barnes is spiraling into the gutter. When Jimmy and Spencer finally come together, an unlikely friendship forms.
The film is notable for being the first screenplay work written by J. J. Abrams.
This film features examples of:
- Boyish Short Hair: With the film released in 1990, it still carries the fashions of the previous decade, but rather than '80s Hair, Jewel Bentley has the short style trendy for women in the '80s.
- Caught on the Jumbotron: Jimmy, a convicted car thief who escapes from prison specifically to attend a world series game for which he won tickets, catches a foul ball during the game that is caught on the Jumbotron. He has to make a swift exit from the stadium shortly thereafter as the cops close in on him.
- Confronting Your Imposter: Jimmy Dworski escapes from jail, finds the Filofax of Spencer Barnes, then impersonates Barnes until the real Spencer Barnes shows up.
- Ludicrous Precision: When Jewel and Jimmy end up having sex, they both claim it was the best sex they ever had, but Jimmy, having previously been in prison, feels the need to get more specific.Jewel Bentley: That was the best sex I've ever had!
Jimmy Dworski: That was the best sex I've had in 2 years, 11 months, 3 weeks and 5 days!
- Radio Contest: The premise of the movie involves a convict winning tickets to the World Series, but still having several days to serve in prison. The contest was simple: Name the first four albums of Led Zeppelin. (Which were, 1,2,3 and lacking a pronounceable name - 4.)
- Shout-Out: Jimmy's reaction after entering Spencer's mansion for the first time after finding the key and alarm codes in the Filofax is, "Wow! I'm on fucking Dynasty!"