This movie was reportedly based on the real-life experiences of its writers, former Second City troupe members and WKRP in Cincinnati writers Steven Kampmann and William Porter.
In the final ballgame, Billy Wyatt pinch hits for "Costner". Former UCLA quarterback Mark Harmon replaced original choice and baseball enthusiast Kevin Costner in the starring role.
The beach house scenes were shot at the same place as the famous "shrinkage" episode on the television series Seinfeld (1989).
One of the film's shooting locations is Chestnut Hill Academy, a school near Philadelphia, Pennsylvania which Steven Kampmann is a graduate of. Thacher Goodwin, who plays the young Billy Wyatt, was a student in 5th grade there at the time.