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.
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 Back to School (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, because of the use of the gopher in this sequel, Bill Murray, who was involved in its creation in Caddyshack (1980), but himself did not reprise his role as the greenskeeper in this sequel, sued the producers during post-production, with the case being settled out of court with an undisclosed settlement.
During one of the underground shots of the gopher, we see an assortment of junk that he's collected in his "home". If you look closely, there is a plastic explosive (C-4) animal in the background, which was used by Carl (Bill Murray) in the first film. Carl dropped the clay animal in the hole, in an effort to kill the gopher.
According to the article "Dangerfield is picky about scripts for his movies" published in the September 27, 1988 edition of the St. Petersburg Times, Rodney Dangerfield, after mandating several re-writes of the script, withdrew from the movie, feeling that the picture would be unsuccessful.
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.
The picture was nominated for four Golden Raspberry Awards, including Worst Picture and Worst Actor (Jackie Mason). The movie won two Razzies, for Worst Original Song ("Jack Fresh") and Worst Supporting Actor (Dan Aykroyd).
Reportedly, according to the article "Dangerfield Sued" in the November 4, 1987 edition of the Fort Lauderdale Sun Sentinel, Warner Brothers sued Rodney Dangerfield for refusing to appear in the movie.
Rodney Dangerfield was going to come back to play Al Czervik again for this movie, but rejected the role, because Writers (Harold Ramis and Pj Torokvei) would not let him tweak the script. As a last resort, Jackie Mason accepted to play the role, but as Jack Hartounian.
One of two 1988 feature films starring Chevy Chase. The other was Funny Farm (1988). This movie bombed at the box-office, while Funny Farm made a small profit. Chase also cameoed in the box-office bomb The Couch Trip (1988).
As with Caddyshack (1980), the name of the private Members-Only club was "The Bushwood Country Club". The name, to which it got changed, when it got taken over by Jack Hartounian (Jackie Mason), was "Jacky's Wacky Golf".