All five of this film's lead actors (Louie Anderson, Richard Lewis, Richard Belzer, Franklyn Ajaye, and Tim Thomerson) have backgrounds in stand-up comedy, and this film was largely an attempt to capitalize on the popularity of televised stand-up in the mid-to-late 1980s and the relative fame of these comics.
According to Louie Anderson, Sam Kinison was originally intended to play the role of the villain Duke Earle, who ended up being played by John Goodman.
Bunny Summers played the mother of Louie Anderson once before, in Unaired Pilot (1986), before Anderson was re-cast with Mark Linn-Baker when Perfect Strangers (1986) went to series.
A poster for the Rocketeer appears in Louie's room in the opening credits. The Rocketeer was created in 1982 as a throwback to the Saturday morning serial heroes of the '30s - '50s. While anachronistic for a room preserved since the early '60s, writers Danny Bilson and Paul De Meo had been working to bring the comic to the big screen since 1985 and would go on to co-write The Rocketeer (1991).
Writer/director Danny Bilson has said this was inspired in part by his childhood experience of scouting with the themes of family and friendship as an emotional center of the film coming from the stand-up of Louie Anderson.