Chevy Chase was the only original cast member to return for this movie, and he later regretted the decision. Producers also begged Rodney Dangerfield to return. Upon reading the script, he reportedly threw it in the trash can.
Some trailers for the original Los locos del golf (1980) included a voice-over by Chevy Chase, stating, "Better than Caddyshack II."
In a 1999 interview with The A.V. Club, Harold Ramis said of this sequel: "with Caddyshack II (1988), the studio begged me. They said, "Hey, we've got a great idea: 'The Shack is Back!'" And I said "No, I don't think so." But they said that Rodney (Dangerfield) really wanted to do it, and we could build it around Rodney. Rodney said, "Come on, do it." Then the classic argument came up which says that if you don't do it, someone will, and it will be really bad. So I worked on a script with my partner PJ Torokvei, consulting with Rodney all the time. Then Rodney got into a fight with the studio and backed out. We had some success with De vuelta al colegio (1986), which I produced and wrote, and we were working with the same director, Alan Metter. When Rodney pulled out, I pulled out, and then they fired Alan and got someone else (Allan Arkush). I got a call from (co-Producer) Jon Peters saying, "Come with us to New York; we're going to see Jackie Mason!". I said, "Ooh, don't do this. Why don't we let it die?", and he said, "No, it'll be great." But I didn't go, and they got other writers to finish it. I tried to take my name off that one, but they said if I took my name off, it would come out in the trades, and I would hurt the film."
Reportedly, during post-production, Chevy Chase said to Director Allan Arkush, "Call me when you've dubbed the laugh-track" and then walked away disgusted.
Sam Kinison was originally cast in this film, but backed out when close friend Rodney Dangerfield (who was to reprise his Al Czervik role from the first film) backed out due to creative differences with the script. It is believed that Kinison was to portray the "Peter Blunt" character. The role eventually went to Randy Quaid.