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THE REWATCHABLES · June 15, 2021

City Slickers

A 1991 comedy / western directed by Ron Underwood, covered in the complete Rewatchables archive.

ComedyWestern1990sDirected by Ron Underwood
Overall episode#207Source sheet order
Movie year19911990s
Tomatometer84%Critics’ score
Metacritic70View score
Roger Ebert—No review recorded
DirectorRon UnderwoodComedy / Western

FROM THE CONVERSATION

What they said about the movie

The episode argues that City Slickers is a corny but highly rewatchable yuppie-midlife-crisis comedy that works because of Billy Crystal’s persona, the strong three-hander chemistry, and a script that mixes sentiment with jokes. The hosts treat it as a once-common kind of movie star vehicle that feels unusual now, while also poking at its later-movie problems, especially its ending and some weird plot choices.
Based only on this episode’s transcriptTimes approximateSpeakers were clearly identifiedExplore the connections

WHY IT WORKS

What made it rewatchable

  1. 01Billy Crystal’s one-liners and midlife-crisis comic timing are a major draw. About 32 min
  2. 02The trio’s horseback banter and buddy chemistry feel lived-in and funny. About 8 min
  3. 03Jack Palance’s Curly scenes are memorable despite his limited screen time. About 16 min
  4. 04The film’s sentimental script and heart give it more staying power than a standard broad comedy. About 8 min

WHAT DID NOT WORK

Their main criticisms

  1. moderateThe last stretch of the movie falls apart and loses momentum. About 32 min
  2. moderateThe two drunk cattle hands are a bizarre and unnecessary late-movie tension device. About 40 min
  3. minorThe opening title sequence and score feel overlong and corny. About 40 min
  4. minorBilly Crystal’s Mets-hat/backstory logic does not make sense within the film’s timeline. About 32 min
  5. minorCity Slickers 2 is treated as a money-grab follow-up rather than a worthy sequel. About 8 min

SCENES THEY KEPT COMING BACK TO

Standout moments

Favorite

Airplane jokes after the running-of-the-bulls trip

The hosts love the post-trip banter, especially Billy Crystal’s and Bruno Kirby’s dad jokes.

About 24 min
positive

Crystal-Tambor pizza/advice scene

A favorite scene where Crystal’s character is confronted with the age-crisis idea.

About 32 min
Favorite

Best day / worst day speech

Bruno Kirby’s monologue about his father is singled out as the strongest scene.

About 32 min
positive

Harmonica scene with Curly

Crystal and Palance’s quiet conversation is treated as one of the movie’s best emotional beats.

About 40 min
Favorite

Classroom life-speech

Billy Crystal’s life-stages monologue is praised for its humor and structure.

About 48 min
positive

Ben and Jerry’s food-pairing scene

The ice-cream menu matching gag is treated as an excellent comic set piece.

About 56 min
positive

Pregnancy confrontation at the grocery store

The Daniel Stern and cashier scene is called very funny and awkward.

About 32 min
critical

Cow-ownership refund ending

The ending with the cattle refund is mocked as absurd and undercutting the danger the characters faced.

About 1:04

WHERE THEY DISAGREED

The biggest debates

They partly agreed About 16 min

How good Jack Palance’s Oscar win really was

Bill Simmons

It is justified as a lifetime-comedy acknowledgement despite limited screen time.

Chris Ryan

The win is understandable but mostly puzzling because he is barely in the movie.

Sean Fennessey

The category was weak, so the win makes some sense as a career honor.

No final agreement About 1:04

Whether Curly should have died

Bill Simmons

The death is a key structural choice but also feels like where the movie loses steam.

Chris Ryan

The film could maybe have worked if Curly stayed alive longer.

Sean Fennessey

The death is the central test of the story and part of the script’s design.

They agreed About 16 min

Whether Billy Crystal was more like a TV host or movie star

Sean Fennessey

He was a reason to go see a movie and a major star in his era.

Chris Ryan

He was like an all-purpose entertainment presence who played himself across media.

Bill Simmons

His fame came from doing everything well, especially in public-facing formats.

They partly agreed About 32 min

The baseball continuity in Mitch’s backstory

Bill Simmons

The Mets/Yankees story makes no sense given the film’s timeline.

Sean Fennessey

The script includes it because of real-life and/or comic-relief reasons.

20 People discussedActors, directors, writers, and producers
very favorableBilly CrystalBill Simmons: Praised as the movie’s apex and a star who always knows how to play himself in a likable, hangout-friendly way. About 8 min favorableJack PalanceBill Simmons: Admired for winning an Oscar despite limited screen time; his Curly performance and ‘one thing’ speech stand out. About 16 min favorableBruno KirbySean Fennessey: Praised as a great scene partner and alpha presence in the trio, with a strong New York-guy vibe. About 24 min favorableDaniel SternChris Ryan: Seen as a perfect schlubby middle-aged comic lead whose nervous energy helps the movie work. About 8 min
favorableRon UnderwoodSean Fennessey: Described as a safe pair of hands with a strong start in Tremors and a mixed later career. About 40 min
neutralMitch RobbinsDiscussed as Billy Crystal’s character and the film’s midlife-crisis center. About 8 min
favorableCurlyCurly is treated as the movie’s wise cowboy guide and source of the ‘one thing’ idea. About 16 min
mixedPatricia WettigBill Simmons: Mentioned as the wife character who is serious and less playful than the movie’s men. About 16 min · medium confidence
favorableJeffrey TamborSean Fennessey: Praised for the Crystal-Tambor scene and for helping set up the movie’s emotional premise. About 32 min
favorableBen and Jerry’s guysBill Simmons: The ice-cream pairing bit is held up as a very funny supporting performance. About 56 min
neutralHarvey KeitelMentioned in discussion of the 1991 Oscar supporting-actor slate and Bugsy. About 16 min · medium confidenceneutralBen KingsleyMentioned as part of the Bugsy supporting-actor Oscar discussion. About 16 min · medium confidencefavorableTommy Lee JonesCited as a stronger Oscar contender in JFK than some of the actual nominees. About 24 min · medium confidencevery favorableLawrence FishburneBill Simmons: Cited as the best supporting-actor choice that year, even though he was not nominated. About 24 min neutralCharles BronsonBill Simmons: Discussed as a rejected early choice for Curly, based on a story Crystal tells. About 1:04 neutralRick MoranisSean Fennessey: Mentioned as the original Phil casting before Daniel Stern replaced him. About 1:04 favorableJake GyllenhaalBill Simmons: Referenced as the young actor playing Crystal’s son and as a good-looking, lasting star image. About 24 min neutralHelen SlaterBill Simmons: Mentioned as the actress playing the female camper/romantic interest and as a Supergirl reference point. About 48 min neutralYardley SmithBill Simmons: Identified as the cashier in the pregnancy scene. About 32 min
favorableNoble WillinghamBill Simmons: Named as one of the memorable supporting players, especially in the cattle-business scenes. About 56 min
12 Conversation takesSpeakers shown only where the transcript identifies them
Bill SimmonsLiked it

City Slickers

Calls it a corny midlife-crisis movie that is incredibly rewatchable.

Opening minutes
Chris RyanLiked it

City Slickers vs. modern comedies

Says modern versions of this movie would be much darker or more contrived.

Opening minutes
Sean FennesseyLiked it

City Slickers

Frames it as the culmination of the yuppie-in-crisis comedy cycle.

About 8 min
Bill SimmonsLoved it

Billy Crystal

Argues Crystal is at his career peak here and one of the most important stars of the era.

About 8 min
Sean FennesseyLoved it

Billy Crystal

Says Crystal is a reason people went to the movies and mastered hangout-style scenes.

About 16 min
Chris RyanLoved it

Horseback banter and road-trip conversations

Prefers the scenes where the men are just talking and joking on horseback.

About 24 min
Sean FennesseyLiked it

Jack Palance

Acknowledges the performance is good but notes the Oscar came from a tiny amount of screen time.

About 16 min
Bill SimmonsLoved it

Bruno Kirby

Loves Kirby’s alpha New Yorker energy and sees him as a major ingredient in the movie’s chemistry.

About 24 min
Chris RyanLoved it

Best day / worst day speech

Calls the Bruno Kirby monologue one of the film’s best scenes.

About 32 min
Bill SimmonsLoved it

Billy Crystal’s classroom monologue

Admires the age-through-life speech as very strong scriptwriting.

About 48 min
Sean FennesseyLiked it

Ron Underwood’s direction

Describes the film as well-shot and appropriately Western-looking despite its corniness.

About 40 min
Bill SimmonsLiked it

Stampede and river-crossing tension

Thinks the movie’s western-fish-out-of-water elements are the right kind of absurd.

About 48 min
5 ThemesThe larger ideas in the discussion

Midlife-crisis comedy

The movie is framed as a Reagan-era/yuppie crisis story about successful men wondering what life means at 39.

Opening minutes

Billy Crystal as a specific kind of movie star

They argue that Crystal was a major star by the early 1990s because he could host, perform, and anchor movies while still feeling like himself.

About 16 min

Sentimentality inside comedy

The hosts admire how the movie mixes jokes with sincere emotional stakes instead of tacking on heart at the end.

About 8 min

Fish-out-of-water western

The absurdity of normal men on a cattle drive is central to why the movie works.

About 24 min

Rewatchable star chemistry

They emphasize the pleasantness of hanging out with the characters, especially in conversational scenes.

About 24 min
23 Facts and referencesProduction notes and other movies mentioned

Production note

City Slickers cost about $26 million and made about $180 million.

About 24 min

Production note

Jack Palance arrived in the film around the 35th minute and was gone by about the 53rd minute.

About 16 min

Production note

Crystal says he came up with the movie after watching a TV show about middle-aged men on fantasy vacations.

About 1:04

Production note

The hosts say 10 or 11 cows were used for Norman, the calf.

About 1:04

Production note

They say the river-crossing and birthing scenes were hard to shoot because the cattle kept mounting each other.

About 1:04

Production note

Billy Crystal’s real daughter Lindsay played his daughter in the film.

About 1:04

Production note

Rick Moranis was originally cast as Phil before Daniel Stern replaced him.

About 1:04

Production note

The hosts say Crystal was 43 during filming but played like a man in his late 40s or 50s.

About 48 min

When Harry Met Sally

Used as a key Billy Crystal comparison and as a predecessor in Crystal’s career arc.

About 8 min

Running Scared

Cited as another Billy Crystal film where he felt like a real buddy on screen.

About 16 min

The Princess Bride

Mentioned in Crystal’s career overview.

About 8 min

The Cowboys

Cited as a story source for City Slickers’ basic setup.

About 1:04

Shane

Used in the Jack Palance Oscar discussion.

About 24 min

JFK

Referenced while debating the 1991 supporting-actor Oscar field.

About 24 min

Bugsy

Discussed as part of the odd Oscar nominee slate.

About 16 min

Boyz n the Hood

Referenced as the film many thought Lawrence Fishburne should have been nominated for.

About 24 min

The Legend of Billie Jean

Used in a running bit about internet origin and the cashier actress Yardley Smith.

About 32 min

Seinfeld

Referenced in a comparison about city guys and baseball talk.

About 56 min · medium confidence

Soap

Used to explain Billy Crystal’s early fame.

About 8 min

Saturday Night Live

Discussed as a major turning point in Crystal’s career.

About 8 min

The Fisher King

Part of the 1991 Oscar discussion.

About 24 min

The Doors

Mentioned as a major Oscar snub year.

About 24 min

What About Bob?

Mentioned as another Oscar snub candidate.

About 24 min
12 Running jokes and short linesRecurring bits captured from the conversation

Billy Crystal apex mountain

Repeated gag that this movie and era mark Crystal’s absolute peak as a star.

About 8 min

Apex/Oscar one-upmanship

They tie City Slickers, Crystal’s Oscars hosting, and Palance’s win into one apex narrative.

About 16 min

Legend of Billie Jean created the internet

A recurring exaggeration that the film foretold modern internet culture.

About 32 min

Gans and Mandel / Lowell and Babalu praise

The writers are humorously treated as a great comedy factory with a lot of output.

About 8 min

One thing

Curly’s ‘one thing’ advice becomes a running philosophical joke about life priorities.

About 16 min

Mets/Yankees continuity nit

Bill repeatedly fixates on the impossible baseball backstory in Mitch’s monologue.

About 32 min

City Slickers 3 pitch

They invent a sequel/legacy-series idea with aging characters and a new cattle drive.

About 56 min

Bill Simmons

“I'm as good as I'm ever going to look.”
About 8 min

Chris Ryan

“Soon you'll be dating sperm.”
About 24 min

Bill Simmons

“If you stick to that and everything else”
About 48 min

Bill Simmons

“This movie is the fifth biggest movie”
Opening minutes

Chris Ryan

“I'm on vacation. Shut the hell up.”
About 40 min

MAKE IT A MOVIE NIGHT

Where to watch

UNITED STATES

Checking where City Slickers is available…

WHAT TO WATCH NEXT

Movies to watch before and after.

Three movies to watch before City Slickers, and three to watch next.

Finding six movies…Three to watch first and three to watch next.
Includes a Rewatchables episodePosters from TMDB.

ON THE MIC

3 voices on this episode

Bill Simmons headshotBill SimmonsThe Rewatchables
Chris Ryan headshotChris RyanThe Rewatchables
Sean Fennessey headshotSean FennesseyThe Rewatchables

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