- Actor Allusion: In the second film, Glenn (played by Jon Lovitz) tried to "milk" Norman. This could be an allusion to his character in A League of Their Own, who chaffed at the characters played by Geena Davis and Lori Petty milking cows.
- AFI's 100 Years… 100 Laughs: #86
- The Other Darrin: In the Mexican Spanish dub of the first film, Phil Berquist and Barry Shalowitz were respectively voiced by Marcos Patiño and Eduardo Borja. In City Slickers 2, they were replaced Mario Castañeda and Miguel Ángel Ghigliazza, respectively.
- Real-Life Relative: Mitch's daughter is played by Billy Crystal's real-life daughter Lindsay. Her older sister appears as a jogger in City Slickers 2.
- Reality Subtext: Billy Crystal tells the true story of the first baseball game he went to.
- What Could Have Been: Rick Moranis was supposed to be in City Slickers, but declined the offer to take a break and care for his wife Ann, who was very ill at the time (she died shortly thereafter and Moranis semi-retired from acting to take care of his children).
- Bruno Kirby (Ed from the first movie) declined to be part of the sequel in part because he was highly allergic to horses and required constant allergy treatments to do his scenes.