Weird History
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9 Behind-The-Scenes Stories From 'City Slickers'

Updated September 23, 2021 2.5k votes 437 voters 17.7k views9 items

List RulesVote up the 'City Slickers' stories that help you appreciate the '90s comedy classic.

First released in 1991, City Slickers has become a cherished classic. It perfectly captures the experience of men struggling with midlife crisis and doubting their own masculinity, and manages to be a hilarious comedy, a rousing adventure, and a touching drama all at the same time. It also has a quality of so many '80s and '90s movies: It seems to belong to a simpler, pre-internet, pre-smartphone world some little part of people aches to return to.

Shooting City Slickers was, according to its lead actors and director, a wonderful experience. Billy Crystal and his co-stars really got to do all the fun cowboy-ish stuff their characters do. Even so, like any movie shoot, it was not without its hitches, quirks, and surprises. 

  • 5

    The Actors Actually Drove The Cattle Around Between Takes

    City Slickers was made in 1991, before CGI was used to do much more than render magical morphing and hallucinogenic stained-glass knights. In those days, if you wanted to make a movie about driving cattle, you had to actually drive cattle around - repeatedly, if you needed to do a lot of takes.

    Billy Crystal, Daniel Stern, and Bruno Kirby got so much practice at herding cattle that they were able to do a cowboy's job - not only when the cameras were rolling, but between takes, too. In the DVD commentary, Stern recalled:

    Even in between takes, after a while, we'd do a take where we'd walk down and herd the cows, and on the turnaround to set up for the next take of that, we would herd the cattle back. It just sort of became part of the life.

    Crystal added, "We would tell the cowboys, who were our herders, 'Nah, it's okay, we got 'em.'"

  • 6

    The Birthing Scene Used Fake Cow Parts And A Real Calf

    Around the film's midpoint, Mitch helps Curly deliver a calf - sealing his bond with the cantankerous cowboy, and turning a corner into becoming the kind of "real man" he hopes the vacation will turn him into.

    The scene is filmed in unsettlingly realistic detail - including a couple of cutaways of an actual calf coming out of what appears to be an actual birth canal. Well, the calf is real, but the birth canal isn't.

    Billy Crystal explained in his memoir how it was done:

    Our special effects crew created the rear section of a cow. It was a perfect anatomical replica, complete with "lungs" that would breathe as a cow in distress would. They covered a few-days-old runt calf in realistic bloody jelly and folded the little guy up, and I pulled him out of the faux birth canal.

    Because of the scene's realism, Crystal wrote, people ask him what it's like to birth a calf, even though he never actually did that.

  • 7

    Billy Crystal Wrote Out The Storyline In A Few Lines On A Notepad

    Billy Crystal got the idea for City Slickers after watching a TV series about fantasy vacations. In the DVD commentary, Crystal recalled the genesis of the concept:

    I just sat there and went, "Huh." Picked up a pad, and saw it. I wrote, "three friends, a midlife crisis, they go on a cattle drive, secrets that friends have from each other, crusty trail boss" - and I wrote "Jack Palance" - "dies, they have to bring in the herd themselves." And I still have it - that was like the half-a-page [synopsis].

    Crystal, who had just signed a production deal with Castle Rock Entertainment, pitched the idea to founders Martin Shafer and Rob Reiner, who loved it. They brought on veteran scribes Lowell Ganz and Babaloo Mandel to write the screenplay.

  • 8

    Jake Gyllenhaal Really Could Pop His Shoulder Out

    City Slickers was Jake Gyllenhaal's first role in a movie. Just 10 years old at the time, he played Mitch's son Danny. "He had great instincts," Crystal recalled in the DVD commentary. Crystal, who was friends with Gyllenhaal's family, said Jake would perform songs from The Phantom of the Opera at parties. Crystal introduced the boy to director Ron Underwood, and Jake was cast.

    The party scene opens with Danny clowning for the guests and showing off how he can pop his shoulder out. Crystal recalled that "Jake could [really] pop his shoulder out," and this bit of business was Gyllenhaal's idea.

    "I got all these toys and things for him to use in the scene," Underwood recalled, "and he said, 'Look at this, what I can do!'"