- Actor-Shared Background: The vast majority of the main cast is from either New York City or New Jersey.
- Cast the Runner-Up:
- Originally, Ray Liotta wanted the role of Sheriff Freddy Heflin, while Sylvester Stallone wanted the role of Gary "Figgsy" Figgis.
- The role of Ray Donlan was first intended for John Spencer, who was then cast as Leo Casky.
- The Danza: Frank Vincent plays Vincent LaSalle, head of the patrolman's union.
- Deleted Role: Debbie Harry acted in the movie but was edited out in the final cut. She explained on a live television special that although she was cut, she still got paid.
- Deleted Scene: Two deleted scenes primarily show the racism in the town of Garrison. One scene involves all the resident police officers chasing down a pair of black motorists, and the other shows Heflin's deputy pointing out that the majority of the tickets issued in Garrison go to black motorists on charges that suggest racial profiling.
- Doing It for the Art: A big deal was made in the press about Sylvester Stallone working for scale in this movie. The fact that he had just been paid $20 million to star in Judge Dredd probably made this decision easier.
- Dyeing for Your Art: Sylvester Stallone lost much of his musculature and gained a lot of blubber for the role as small town sheriff Freddy Heflin. He gained the necessary weight for the role by eating a steady diet of giant pancakes served at a local pancake house.
- Playing Against Type: Sylvester Stallone convincingly plays a conflicted sheriff with emotional depth, and even has a different physique in this film than that for which he is known.
- Romance on the Set: During the shooting, James Mangold fell in love with producer Kathy Conrad. She later became his wife and has continued to produce many of his other movies.
- Star-Derailing Role: Zigzagged for Sylvester Stallone. While the film posted solid box-office takings, got good reviews, and Stallone received positive critical notices for his performance as a demure small-town sheriff, in 2008 the actor stated on The Opie and Anthony Show that the film "hurt" his career and that he had trouble getting roles for eight years, due to the film's failure to reach the high expectations set for it and the mix of views on whether he was leaving action movies for more character-driven content. Stallone has described this as "the beginning of the end, for about eight years". In a 2019 interview he called James Mangold "the best director I ever worked with" but said the film was bad for his career: "I loved the film, but it actually worked in reverse. It was pretty good critically, but the fact that it didnít do a lot of box office, again it fomented the opinion that I had my moment and was going the way of the dodo bird and the Tasmanian tiger."
- Throw It In: Robert De Niro improvised the sandwiches in his scene, which were an afterthought.
- What Could Have Been: Tom Cruise, Tom Hanks, Gary Sinise and John Travolta were considered for Sheriff Freddy Heflin.
- Write What You Know: Although it is stated during in the credits that the movie isn't based on a true story, James Mangold did grew up in Washingtonville, New York, which was a place where lots of policemen's families lived. In an interview, he mentioned that the film was based on his experiences of growing up in his hometown among the many children of these cops.
Trivia / Cop Land