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.
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.
Warner Bros. green-lit the movie after Herman Raucher denied them the rights to remake Summer of '42 (1971).