City Slickers

Classic Western movie poster, just add Billy Crystal!

City Slickers (1991) is a comedy film, directed by Ron Underwood. The main stars were Billy Crystal, Daniel Stern, Helen Slater, Jack Palance and Bruno Kirby. The film is about a group of men experiencing a collective midlife crisis. Phil Berquist (Stern) is stuck managing his father-in-law's grocery store, while trapped in a sexless marriage with an overbearing wife, and Ed Furillo (Kirby) is a successful businessman and playboy, struggling with the idea of monogamous marriage and the pressure to have kids.

At the 39th birthday party of Mitch Robbins (Crystal), 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 (Palance).

Jack Palance won an Academy Award for Best Supporting Actor for his role as Curly. City Slickers was followed in 1994 by City Slickers II: The Legend of Curly's Gold, which was not as well-received as the original.

Tropes used in City Slickers include:

Animated Credits Opening
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 Marc Shaiman.
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 Grandpa: Curly and Duke.
Camp Cook: He gives a brief but memorable eulogy at Curly's funeral.
Cattle Drive: The whole premise of the first movie.
City Mouse: The entire cast.
City Slicker: Pretty much the entire cast.
Closest Thing We Got: The two dentists.

"We're the only ones with any medical training."
"What exactly are we gonna do, Dad, give him a cleaning?!"

Dies Wide Open/Died On His Horse: Curly. It takes several minutes for Mitch & Co. to realize he's dead.
Dropped a Bridget On Him: 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.

Hand Wave: in Legend, Duke's asked where he's been during his time away from Curly. He responds "You writin' a book?" and no-one asks him that question again.
Heroes Want Redheads: Curly's story about his greatest love.
If You Die, I Call Your Stuff:

"If anything happens to him...I'm going after Barbara."

It Got Worse: From the second movie:

Mitch: You ever walk in on our parents doing it?
Glen: No, have you?
Mitch: Yeah.
Glen: That's a horrible thing for a little kid to see.
Mitch: This was last week in Florida!
Glen: Uhh!
Mitch: It was on the kitchen table.
Glen: Uhhh!
Mitch: And an hour later we ate on that table!

MacGuffin Escort Mission: The cattle drive.
Never Mess with Granny:

Duke: My Ma died last year, she was 95. Stabbed in a bar fight.

Open-Heart Dentistry: See Closest Thing We Got above.
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.
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.
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.
Replacement Goldfish: Mitch's brother Glenn replaced Ed in the sequel.
Right Behind Me: Occurs in both movies, both times executed by Mitch (twice in II).
Screams Like a Little Girl: Well, Daniel Stern in general.
Sequel Hook: Duke found the missing piece of the map and a gold bar as proof of the treasure's existence.
- Though they likely never really intended to follow through on it, a third film would have had exactly the same plot as II, just with a different ending.
Shout-Out: To The Treasure of the Sierra Madre in II, a lot.
Staged Shooting: At the end of City Slickers II, 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.
Taking the Bullet: Parodied in City Slickers II, when Glen takes a bullet for Billy Crystal's character, 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."
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.
You Wouldn't Like Me When I'm Angry: Curly's burial:

Cookie: Lord, we give you Curly. Try not to piss him off.