The film is about a group of New York City-based men experiencing a collective midlife crisis. Mitch Robbins (Crystal) is an advertising manager at the WBLM radio station who's increasingly disillusioned with the lack of meaning he sees in his job and his life. Phil Berquist (Stern) is stuck managing his father-in-law's grocery store, while trapped in a sexless marriage with his overbearing wife Arlene (Karla Tamburrelli). And Ed Furillo (Kirby) is a successful businessman and playboy, struggling with the idea of monogamous marriage and the pressure to have kids.
At Mitch's 39th birthday party, Phil and Ed present their joint birthday present: a two-week Southwestern cattle drive for all three men. At the insistence of his wife Barbara (Patricia Wettig), Mitch accepts the gift, traveling with his friends to New Mexico, where they meet the other participants of the cattle drive and learn the ropes of moving the herd, guided by the grizzled, tough-as-nails boss of the whole operation, Curly Washburn (Palance).
Jack Palance's performance as Curly won him the 1991 Academy Award for Best Supporting Actor and AFI ranked the film as #86 on its "100 Years...100 Laughs" list. Followed in 1994 by City Slickers II: The Legend of Curly's Gold, which was not as well-received as the original.
These films contain examples of:
- 20 Minutes into the Past: The sequel begins on Mitch's 40th birthday. Since he was born in 1952, that means the film is set in 1992 (two years before its release).
- 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.
- Actually Pretty Funny: Mitch accidentally causing a stampede? Curly chuckles and shakes his head.
- And Starring: The first film's main cast roll ends with "and Jack Palance".
- Animal Stampede: Mitch's coffee grinder starts a stampede of the cows.
- Animated Credits Opening: The animated main titles begin after the bull gores Mitch from behind in Pamplona.
- Ass Shove: A variant happens to Mitch in the first film during the Running of the Bulls, getting gored by one of the horns in one of the cheeks before the opening credits. After said credits, he's seen at a doctor getting fixed up.
- Automaton Horses: Consciously averted, as the main characters' lack of riding experience is played for laughs.
- Award-Bait Song: "Where Did My Heart Go?" by the late James Ingram appears in the end credits.
- Awful Wedded Life: All scenes and dialogue make it obvious that this is the case between Phil and Arlene.
- Backup Twin: City Slickers II has this in the form of Duke, Curly's equally-scary twin brother. The reason given for his absence, and not even being mentioned, in the first movie is that he and Curly weren't on speaking terms, he was out on the sea, and Curly didn't exactly talk about his personal life to a guy he met yesterday all that much anyway.
- Badass Boast: Curly's "I crap bigger than you." Yes.
- Benevolent Boss: Lou, the manager at Mitch's radio station. While initially angry, Mitch recognizes that Lou had every right in the world to be angry about the ad that he bought and realizes it's his responsibility to do his job better, and that rather than complaining, he should be grateful that he has a decent boss. Later, when Lou learns about what Mitch is going through, he's polite enough to sympathize with him.
- Beware the Nice Ones: The nerdy, mild-mannered Phil finally loses it with Jeff and is absolutely terrifying, pointing Jeff's own gun at him, cocking the trigger and seeming like he was genuinely about to kill him.
- Big Little Brother: Mitch's brother Glen in the second film (Billy Crystal is 5'6" while Jon Lovitz is 5'9"). Glen even lampshades this in his first scene.
- Cactus Cushion: In the second film, Phil thinks he got bitten by a rattlesnake while trying to take a dump, but when Mitch goes to suck out the poison he finds cactus needles instead.
- Calling the Old Man Out: When they guys are sharing the stories of their Best Days, Ed talks about the day when, as a 14-year-old kid, he stood up to his abusive, adulterous father and told him to get out of their lives and that he would take care of his mother and sister himself...and he did.Phil: [incredulous] What was your worst day???
Ed: Same day.
- The Casanova: Ed is a womanizer who fears monogamy, and he's dating a model.
- Camp Cook: He gives a brief but memorable eulogy at Curly's funeral.
- Cattle Drive: The whole premise of the first movie.
- Celebrity Paradox: In the sequel, Glen likes to quote The Godfather Part II. Bruno Kirby, who played Ed in the first film, played Peter Clemenza in that film.
- The Chew Toy: Phil is never safe from the world's abuse. Examples include being chased by bulls to the point that he is forced to jump onto a flagpole, accidentally sitting on a cactus and mistaking it for a snake bite, or being involved in a sexless marriage.
- City Mouse: The entire cast lives in New York City.
- City Slicker: The eponymous trio. It's also the title of the film.
- Closest Thing We Got: The two dentists."He's injured, and we have medical training.""Dad, we're dentists, what are we gonna do, give him a cleaning?!"
- Comedic Work, Serious Scene: The Best/Worst day scene certainly qualifies. The film is very much a comedy, but the characters' conversations about the best and worst days of their lives is very heartfelt and earnest.
- Cool Old Guy: Curly turns out to be this, once Mitch gets to know him.
- Deadpan Snarker: Mitch, being played by Billy Crystal, has a dry and witty personality.Mitch: Hi, Curly—kill anyone today?Curly: Day ain't over yet.
- Destination Defenestration: When Phil is forced to jump onto a Spanish flagpole to avoid the bulls in Pamplona, another spectator jumps through the nearby store's window.
- Dies Wide Open/Died On His Horse: Curly. It takes several minutes for Mitch & Co. to realize he's dead.
- Dirty Coward: Jeff goes from bullying jerk to almost crying in fear when Phil puts a gun to his head.
- Driven to Suicide: It is implied that Phil was contemplating killing himself for a few seconds before Mitch and Ed come to check on him.
- Empathic Environment: The sun comes out just as Ed and Phil rescue Mitch from the river. It's equally beautiful when they return to the ranch after successfully bringing in the herd.
- Growing Up Sucks: Mitch's message to kindergarten students.Mitch: Value this time in your life, kids, because this is the time in your life when you still have your choices, and it goes by so fast. When you're a teenager, you think you can do anything, and you do. Your twenties are a blur. Thirties - you raise your family, you make a little money and you think to yourself: 'What happened to my twenties?' Forties - you grow a little pot belly, you grow another chin. The music starts to get too loud and one of your old girlfriends from high school becomes a grandmother. Fifties - you have a minor surgery. You'll call it a 'procedure', but it's a surgery. Sixties - you'll have a major surgery, the music is still loud but it doesn't matter because you can't hear it anyway. Seventies - you and the wife retire to Fort Lauderdale. You start eating dinner at two o'clock in the afternoon, you have lunch around ten, breakfast the night before. You spend most of your time wandering around malls looking for the ultimate soft yogurt and muttering: 'How come the kids don't call?' 'How come the kids don't call?' The eighties, you'll have a major stroke. You end up babbling to some Jamaican nurse who your wife can't stand but who you call mama. Any questions?
- Happily Married: Mitch and Barbara and, despite the May–December Romance, Ed and his wife from what little we see of them together.
- Hollywood Mid-Life Crisis: The film about three friends who are each going through their own respective mid-life crisis. Mitch is bored with his job and frightened by how quickly the years seem to be flying by. Phil's Sexless Marriage prompts him to have an affair with a younger coworker, resulting in a pregnancy scare, him losing his job and his wife leaving him. Ed is a successful businessman and womanizer who is frightened by the prospect of settling down and starting a family. The three friends go on a cattle drive vacation, during which they all begin to figure out their lives. Curly lampshades this when talking to Mitch, saying, "You all come up here at the same time", revealing that they're far from the first or only men in their age group to do this.
- I Am Not My Father: Mitch suggests that Ed's drive to succeed comes from wanting to be better than the father who abandoned him and his mother and sister.
- Conversely, his fears of commitment and fatherhood appear to be for the same reason—even after finally marrying, he's reluctant to have children out of fear of turning out like his father.
- If You Die, I Call Your Stuff:"If anything happens to him...I'm going after Barbara."
- Intimate Telecommunications: In the sequel, Mitch's wife makes a phone sex call right when Mitch and his radio station partners were waiting for an important business call to happen. Mitch dives across the table to intercept the call before it goes any further.
- Jerk With A Heart Of Jerk: TR and Jeff are introduced as smarmy, and bullying towards the clients on the cow drive. After Curly dies and they end up in charge, they get more professional and respectful, but within fifteen minutes they've started getting drunk and threatening people.
- The Legend of X: In the title of the sequel.
- May–December Romance:
- "Ed, have you noticed that the older you get, the younger your girlfriends get? Soon, you'll be dating sperm."
- His eventual wife appears to be 10-20 years his junior.
- Milestone Birthday Angst: Mitch turns 39 early in the movie, and he's depressed about being close to turning 40, which isn't helped by the fact when he visits his son's class, his son is ashamed of what Mitch does for a living (selling advertising spots for radio):Mitch: Your twenties are a blur. Your thirties, you raise your family, you make a little money, and you think to yourself, "What happened to my twenties?" Your forties, you grow a little pot belly you grow another chin. The music starts to get too loud and one of your old girlfriends from high school becomes a grandmother. Your fifties you have a minor surgery. You'll call it a procedure, but it's a surgery. Your sixties you have a major surgery, the music is still loud, but it doesn't matter because you can't hear it anyway. Seventies, you and the wife retire to Fort Lauderdale, you start eating dinner at two, lunch around ten, breakfast the night before. And you spend most of your time wandering around malls looking for the ultimate in soft yogurt and muttering "how come the kids don't call?" By your eighties, you've had a major stroke, and you end up babbling to some Jamaican nurse who your wife can't stand but who you call mama. Any questions?
- Nervous Wreck: It doesn't take much for Phil to be sent into hysterics.
- Never Mess with Granny:Duke: My Ma died last year, she was 95. Stabbed in a bar fight.
- No Celebrities Were Harmed: Ira & Berry's Ice Cream = Ben & Jerry's Ice Cream.
- No Party Like a Donner Party: Discussed in II when the group is trying to deal with spending the night out in a freezing thunderstorm with no tent. The reaction to this suggestion by Mitch and Glen is about what you would expect, and eventually they come up with a better plan.Phil: In case we don't make it, and I die first...eat me.
Mitch: Eat you??? I don't even like to talk to you on the phone!
- Open Heart Dentistry: See Closest Thing We Got, above.
- Perilous Old Fool: According to Duke, he and Curly's mom was one of these.Duke: Our mom died. She was 95. Stabbed in a bar fight.
- Polar Opposite Twins: Curly was the more honorable of the two, and also preferred the life of a cowboy. Duke was a conniving sort who loved the sea and joined the Navy. But they appear to have had a mutual respect and have equally threatening presences.
- Posthumous Character: Curly in the second film.
- Punny Name: In the first film, the couple who run the ranches and the cattle drive. Meet Clay Stone and his wife, Mill(ie) Stone.
- Rancher: The ranch owner who needs the cattle drive done.
- Reasonable Authority Figure: Lou is competent in his job as WBLM's station manager, deeply cares about Mitch and family and is even willing to let him go on break so he can get his life back on track.
- Reckless Gun Usage: Phil wrestles for one of the trail hands' guns and uses it to scare them into sobering up. Even after the situation has been defused (Phil yells "BANG!" instead of shooting), he keeps his finger tight on the trigger and is clearly agitated.
- Redemption in the Rain: The guys all overcome their respective personal problems after the sequence where they drive the cattle through a raging river in the middle of a storm.
- Replacement Goldfish: Mitch's brother Glenn replaced Ed in the sequel.
- Ridiculously Cute Critter: Norman the cow. Mitch goes to great lengths to protect that little calf and ends up keeping him as a pet.
- Right Behind Me: Occurs in both movies, both times executed by Mitch. (twice in II)
- Screams Like a Little Girl: Phil Berquist, as played by Daniel Stern, often screams in a high pitch.
- Seinfeldian Conversation: Some of the characters' conversations on the trip, as when they discuss the proper way to record a TV program.
- Serious Business: Ira and Barry ask Mitch to challenge Barry to name a meal to follow up with the right type of ice cream. Mitch's first challenge is a half-assed one, which Barry takes as an insult.
- Sexless Marriage: Phil and his wife Arlene. "That's right! Not having sex for twelve years will do that to a person!"
- Sleeping with the Boss: Nancy, a checkout girl from Phil's store, breaks into a party he's attending to tell him she's pregnant, so this trope has been in play. Played both for drama, and laughs:Ed: ...that's pretty smug advice, coming from a man who mounted an eighteen-year-old checkout girl on the day-old bread rack.Phil: She's twenty, and shut up.Ed: Let me get you hot, Phil: "I need a price. Register Nine, I need a price..."Phil: Cut it out!Mitch: (warningly) Guys...Ed: What did you use for protection, paper or plastic?
- Sleeps with Both Eyes Open: Subverted, where the main character thinks this is happening. Turns out, Curly's really dead.
- Speed Sex: Mitch does this with his wife in the sequel when he notices a piece of paper tucked away in Curly's cowboy hat. While his wife goes into the bathroom after the sex, Mitch pulls it out and notices that it is a secret treasure map.
- Squick: In-Universe. Phil tells the other guys he was watching a horse getting castrated. (Beat) Mitch says, "Well! I'm hungry—how about you?"
- Staged Shooting: At the end of City Slickers 2, the target is so startled that even he doesn't realize he wasn't shot.
- Suck Out the Poison: Subverted. It was a thorn. Please chill.
- Sympathetic Adulterer: Phil, given his Sexless Marriage and Henpecked Husband status. However, while sympathetic, none of his friends condone his behavior, he and Nancy have a pregnancy scare, and he's certain that he'll be financially wiped out in the divorce and lose custody of his children.
- Taking the Bullet: Parodied in City Slickers II when Glen takes a bullet for Mitch, shares some tearful last words with his brother, and black out...then immediately revives upon discovering the bullet was a blank.
- Title Drop: Clay Stone tells the cattle drive group that "You came here city slickers; you're gonna go home cowboys."
- Took a Level in Badass: Curly effortlessly intimidates Mitch throughout the first movie until Mitch finally has enough and stands up to him despite still being terrified of him. This earns Curly's respect, and the two finally begin to bond.Mitch is playing the harmonica by the campfire while Curly sharpens his knife
Curly: Put that away.
Mitch pauses and gives Curly an annoyed look, then continues playing.
Curly: *continues sharpening* I said, put that away.
Mitch: You know, the first time I tried to talk to you, you embarrassed me. So I teased you a little bit, which maybe I shouldn't have done. And now you're sitting there playing with your knife, trying to scare me, which you're doing a good job. But if you're gonna kill me, get on with it. If not, shut the hell up. I'm on vacation.
Curly brandishes the knife and advances on Mitch menacingly while Mitch continues to play nervously, then sits next to him and starts singing along.
- The Topic of Cancer: Mitch describes his worst day as the day his wife found a lump in her breast. Luckily, it was benign, but he clearly spent that time terrified that he might lose his wife.
- Toros y Flamenco: The opening depicts Pamplona's annual Running of the Bulls. Although Phil and Ed flee from the bulls (Phil by jumping on a Spanish flagpole and Ed by getting into the spectators), Mitch gets gored from behind.
- Treasure Map: Subverted in City Slickers II since it was a fake map leading to fake treasure as part of an "adventure tour." Then Double Subverted, when it turns out there was gold hidden elsewhere in the desert..
- Unsettling Gender-Reveal: Interspecies example in the second movie, when Glen decides to help out around the house by milking the cow Mitch acquired in the first movie:Glen: There is something wrong with your cow. I reach under there and I'm pulling, tugging, tugging, pulling, nothing, not a drop.
Mitch: The cow's name is Norman. You were pulling on his dick.
Glen: I'm gonna go wash up.
- What Happened to the Mouse?: Ed wasn't seen or heard from in part 2.
- You Wouldn't Like Me When I'm Angry!: Curly's burial:Cookie: Lord, we give you Curly. Try not to piss him off.
- Your Approval Fills Me with Shame: Ed’s story about standing up to his abusive and adulterous father implies that his dad respected that he had the guts to stand up to him. However that left Ed with a decades long dread that he would turn out like his father and thus making it also his worst day.