'City Slickers'
Yesterday, The Ringer's Bill Simmons, Chris Ryan, and Sean Fennessey were podcasters. Today, they are cowboys. We revisit the 1991 comedy 'City Slickers,' starring Billy Crystal, Bruno Kirby, and Daniel Stern.

Cast
Billy Crystal as Mitch Robbins
Bruno Kirby as Ed Furillo
Daniel Stern as Phil Berquist
Jack Palance as Curly
Helen Slater as Bonnie
Jake Gyllenhaal as Danny Robbins
Jeffrey Tambor as Lou (Mitch's boss)
Directed by: Ron Underwood
Written by: Lowell Ganz, Babaloo Mandel
Notes
- $26 million budget, made $180 million – 5th biggest movie of 1991.
- Jack Palance won Best Supporting Actor despite being in the movie for only about 18 minutes. His one-arm push-ups at the Oscar podium became one of the most famous Oscar moments ever.
- Charles Bronson was contacted for Curly but refused because 'I'm Charles Bronson. I don't die.' Palance then got out of his other commitment and joined the cast.
- Rick Moranis was originally cast as Phil but had to leave production because his wife was diagnosed with cancer. Daniel Stern was added about 3 weeks before filming.
- Crystal came up with the idea watching a TV show about middle-aged men going on fantasy vacations. Borrowed the plot from John Wayne's The Cowboys.
- Ganz and Mandel famously didn't do much research – never went on a cattle drive.
- 10 or 11 different cows were used as Norman. Norman's birth scene was shot in three different states.
- Crystal's 'best day of my life' Yankee Stadium story actually happened in real life.
- Jake Gyllenhaal's film debut at age 10 – Crystal's daughter Lindsay also played his daughter.
- Bruno Kirby did NOT do 'City Slickers' 2. Possible feud with Crystal – Kirby's excuse was he was 'allergic to horses.'
- Crystal turned down Buzz Lightyear in 'Toy Story', which then went to Tom Hanks.
- The movie spawned a 2-year trend of cattle adventure vacations.
- 1991 top 5: Terminator 2, 'Robin Hood: Prince of Thieves', 'Home Alone', Silence of the Lambs, 'City Slickers'.
Categories
Quote from Rog's review:
“Much more ambitious and successful than I expected. The proverbial comedy with the heart of the truth, the tear in the eye along with the belly laugh.”
- Bill: The airplane scene coming back from running with the bulls – sore ass jokes, 'soon you'll be dating sperm,' Daniel Stern pretending to sleep.
- Sean: The 'best day / worst day' campfire scene – Daniel Stern's monologue about confronting his cheating father at 14. 'What was your worst day?' 'Same day.'
- Chris: The scene where Yeardley Smith confronts Daniel Stern about his adultery at the party.
- Also discussed: Crystal/Tambor office scene, the harmonica scene with Jack and Billy, the fireplace fight.
- The midlife crisis angle still works perfectly.
- The shocking Curly death – remains effective on rewatches.
- Young Jake Gyllenhaal's appearance – 'has literally aged wonderfully.'
- Palance's one-arm push-ups Oscar moment.
- Billy Crystal's terrible dad one-liners – 'Women need a reason to have sex. Men just need a place.'
- The classroom monologue about aging through decades.
- The two drunk cattle guys (Jeff) – bizarre, unmotivated villain subplot.
- The last 35-40 minutes falls apart.
- Director Ron Underwood's career IMDB – Tremors, 'City Slickers', then Adventures of Pluto Nash ('all-time bomb').
- The corny score by Marc Shaiman.
- 'City Slickers' 2: The Legend of Curly's Gold.
- Charles Bronson was contacted for Curly but said 'I'm Charles Bronson. I don't die.' Palance ended up winning the Oscar Bronson never won.
- Rick Moranis was originally Phil – had to leave because his wife's cancer diagnosis. Daniel Stern was added 3 weeks before filming.
- Bruno Kirby did NOT do 'City Slickers' 2 – possible feud with Crystal.
- Robert Costanzo (the guy at the school).
- Bill Henderson (the older dentist).
- Tracy Walter as Cookie the cook.
- Daniel Stern's wife Arlene in the party confrontation scene.
- Daniel Stern himself – carrying 'Home Alone' energy.
- Kyle Secor as the mean cowboy.
- Bill: Daniel Stern and Jeffrey Tambor should switch parts – 'Better movie.'
- Chris pitches 'City Slickers' 3 as a 10-episode Netflix series – Jake Gyllenhaal reconnects with aging Mitch (Crystal) who has moved out West.
- Crystal came up with the idea from a TV show about middle-aged fantasy vacations.
- Crystal quote about 10-year-old Jake Gyllenhaal: 'He was always performing. He would sing from South Pacific.'
- 10-11 different cows were used as Norman. Norman's birth scene shot in three different states.
- The river crossing was the toughest scene – 'the cows kept mounting each other.'
- Ganz and Mandel never went on a cattle drive.
- Billy Crystal – yes. 'This is the Billy Crystal apex.'
- Daniel Stern – 'Unquestionably yes.' Billion-dollar box office year ('Home Alone' + 'City Slickers' + Wonder Years narrator).
- Bruno Kirby – no, Godfather Part II (young Clemenza).
- Jack Palance – no, it's Shane.
- Helen Slater – yes, has to be her apex.
- Cattle vacations – yes, the movie spawned a 2-year trend.
- Nobody flips out at age 39 – should be 46.
- Helen Slater going on this cattle drive by herself – 'not buying it.'
- Daniel Stern and Helen Slater ending up together – zero interactions in the movie.
- They didn't bury Curly nearly deep enough.
- Sean's #1 nit: If Crystal's character is 39 and the Yankee Stadium story happened at age 7, that's 1959 – the Mets didn't exist yet. Crystal wore Mets gear as a promotional deal but told a Yankees fan story.
- What did they end up doing with Norman the cow in New York City?
- How did the cow get on the flight?
- If the ranch owner lost those cattle, is his business over?
- How was Palance's cigarette so perfectly dangling but not burning?
- Bill: The first script from Ganz and Mandel; also Curly's hat.
- Sean: The Mets hat from the movie.
Billy Crystal – consensus winner. Directed, starred, rode it to peak fame.
Chris Ryan's pitch: 10-episode Netflix series. Jake Gyllenhaal's character Danny is now his dad's age – reconnects with aging Mitch (Crystal) who has moved out West after divorcing his wife.