Chevy Chase was the only original cast member to return for this sequel 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, actor Bill Murray, who was involved in its creation in Caddyshack (1980), but himself did not reprise his role as the green-keeper in this sequel, sued the producers during post-production with the case being settled out of court with an undisclosed settlement.
According to the article "Dangerfield is picky about scripts for his movies" published in the 27th September 1988 edition of the St. Petersburg Times, Rodney Dangerfield, after mandating a number of rewrites of the script, withdrew from the movie, feeling that the picture would be unsuccessful.
Rodney Dangerfield was going to come back to play Al Czervik again for this movie, but rejected the role because the 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.
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 Bill Murray's character "Carl" from the first film. Carl dropped the clay animal in the hole in an effort to get the original gopher in the Caddyshack (1980).
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 4th November 1987 edition of the Fort Lauderdale Sun Sentinel, the Warner Brothers studio sued actor-comedian Rodney Dangerfield for refusing to appear in the movie.
As with Caddyshack (1980), the name of the private members only club was "The Bushwood Country Club". The name that it got changed to when it got taken over by Jack Hartounian (Jackie Mason) was "Jacky's Wacky Golf".