According to Savage Steve Holland, he and John Cusack did not get along during filming. Cusack was disappointed with their previous collaboration, Better Off Dead (1985) and was angry with Holland. According to Holland, Cusack finally lightened up after that film received good reviews, but Cusack never spoke to Holland again.
Savage Steve Holland did the animation for the film. He was upset that film critics Gene Siskel and Roger Ebert roasted his earlier John Cusack film, Better Off Dead (1985). The two animated bunnies that get blown up at the end of this movie bear a strong (and not accidental) physical resemblance to the movie critics.
When Calamari picks up two women at the dance, the strawberry blonde on the right is director Savage Steve Holland's sister, whose childhood nickname was Squid and is the basis for the little girl in the film, also named Squid.
Joel Murray stated in an A.V. Club interview that he did not think he would be cast as George Calamari because Jeremy Piven was auditioning for the same role and was best friends with John Cusack. To Murray's surprise, Piven was cast as Ty instead and he got the part.