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‘Caddyshack’ With Bill Simmons and Sean Fennessey

August 18, 2020 · Caddyshack (1980) · Comedy · Sport · 1:41:33

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Who Won the Movie

Bill Simmons▶ 11:47Rodney Dangerfield — Multiple beneficiaries: rejuvenated Dangerfield and made him a major star, reinvented Chevy Chase leading to his mid-80s renaissance, established Bill Murray as a movie star after Meatballs, and helped Harold Ramis

Most Rewatchable Scene

Bill Simmons▶ 25:16Multiple scenes: Ty playing golf with Danny ('You take drugs, Danny?'), the country club dinner scene with Al Czervik's one-liners and Judge Smales' outfit, the Baby Ruth pool scene, Ty and Lacey's date where he acts like he's doing Fletch, and the Cinderella story/bishop golf sequence

What's Aged the Best

Bill Simmons▶ 44:26Multiple picks including: fake names (Mitch Kumpstein, Lacey Underall, etc.), Lacey Underall character, her yellow 450SL car, Bushwood CC t-shirts, Billy Beru putter concept, 'Noonan' scene as ultimate what's aged best, Carl washing golf balls scene, Haiti reference, Judge L. Hugh Smells name, Kenny Loggins theme song, 'Oh my arm it's broken' running joke, and Judge Smales's downfall
Sean Fennessey▶ 50:13Agrees with Kenny Loggins theme song ('still whips ass'), acknowledges the Noonan phenomenon, and agrees that Judge Smales getting his comeuppance has aged well

What's Aged the Worst

Bill Simmons▶ 52:09Multiple picks: nobody wearing hats now, golf announcers forcing Caddyshack lines into tournaments, DeNunzio's golf swing and outfit, the gopher isn't funny, Maggie character with unclear Irish accent, Baby Ruth bar as Jaws parody less effective 40 years later, Lou the caddy master being unfazed by explosions, and John Peters' treatment of Cindy Morgan
Sean Fennessey▶ 56:19Agreed on the gopher not being funny and comparing it to adding a fifth comedy style like Muppets/Gremlins that doesn't work, and agreed on the John Peters/Cindy Morgan story being a classic Hollywood pressure situation

Casting What-Ifs

Bill Simmons▶ 1:01:19Mickey Rourke — Mickey Rourke was considered for Danny but wasn't funny enough; thinks Mike O'Keefe was the right choice. Michelle Pfeiffer turned down Lacey Underall because she didn't want nudity. Don Rickles considered for Al Czervik but too mean for the role.
Sean Fennessey▶ 1:03:04Mickey Rourke — Agrees Mickey Rourke would have made it a different movie - more like an Adrian Lyne erotic thriller with him and Michelle Pfeiffer. Notes Rourke was overqualified and would seem like competition for Ty Webb rather than believably landing Lacey.

Joey Pants Award

Bill Simmons▶ 1:07:53Scott Colomby — Tony Denunzio (Scott Columbo) - the guy from Porky's and Caddyshack who was never really seen again
Sean Fennessey▶ 1:07:35Dan Resin — Discussed Dr. Beeper (Dan Resin) as a strong candidate since he doesn't even have a photo on IMDb, but didn't give a definitive pick

Apex Mountain

Bill Simmons▶ 1:14:52Michael O'Keefe — Michael O'Keefe (agrees), Rodney Dangerfield (no - Back to School mid-80s), Ted Knight (retroactively yes for legacy), Chevy Chase (no), Bill Murray (no but pure performance), Cindy Morgan (yes), Cocaine (yes), Golf as sport (yes - great year with Nicklaus winning majors)
Sean Fennessey▶ 1:14:39Michael O'Keefe — Michael O'Keefe - yes, coming off The Great Santini

Picking Nits

Bill Simmons▶ 1:20:00Multiple nitpicks including: Spalding throwing up in Dr. Beeper's car instead of a bush, Lacey walking the entire golf course with Judge Smails, caddy day at the pool being unrealistic, the diving board being too high (10 feet), Lacey wearing high heels with a bathing suit, Judge Smails having a tiny 8-foot boat, the golf course greens being awful and bumpy, Lacey going from Ty Webb to Danny in 12 hours, the judge allowing Danny to replace Al Czervik in the big match, Ty Webb choking despite being established as amazing, Baby Ruth bars not actually floating, and most importantly the judge's terrible decision to accept double-or-nothing when he couldn't lose money until taking that bet
Sean Fennessey▶ 1:22:59Agrees with several of Bill's nitpicks and adds that the golf course at Bushwood looks like a piece of shit with terrible grass, noting he's wondered about Lacey walking the course for years and calling it inexplicable, and concluding that Judge Smails is trash - a dumbass who doesn't know what size boat to buy or how to gamble

Best Quote

Bill Simmons▶ 1:27:45Moose Rocco helped the judge find his checkbook

Probably Unanswerable Questions

Bill Simmons▶ 1:27:57Asked multiple unanswerable questions including who carried more golf clubs (Judge Smails or Al Czervik), greatest sports movie putt, whether the movie created 'poontang', what happened to Rodney Dangerfield's career, alternate plot scenarios, and why there was never a Caddyshack video game
Sean Fennessey▶ 1:28:18Judge Smails carried more clubs because he strikes him as the type who thinks it's important to have multiple irons and woods, and he's mediocre so doesn't know what to take out

Movies Referenced (21)

Cinderella (2015)

4 mentions · Bill Simmons, Sean Fennessey▶ 30:20IMDb ↗Lb ↗

Tin Cup (1996)

3 mentions · Bill Simmons▶ 1:29:19IMDb ↗Lb ↗

Groundhog Day (1993)

2 mentions · Sean Fennessey▶ 3:44IMDb ↗Lb ↗

Pump Up the Volume (1990)

2 mentions · Bill Simmons▶ 1:40:36IMDb ↗Lb ↗

The Blues Brothers (1980)

2 mentions · Sean Fennessey▶ 16:24IMDb ↗Lb ↗

Top Gun (1986)

2 mentions · Bill Simmons, Sean Fennessey▶ 49:36IMDb ↗Lb ↗

Beautiful Girls (1996)

1 mentions · Bill Simmons▶ 1:20:56IMDb ↗Lb ↗

Beverly Hills Cop (1984)

1 mentions · Sean Fennessey▶ 16:10IMDb ↗Lb ↗

Casablanca (1942)

1 mentions · Sean Fennessey▶ 9:36IMDb ↗Lb ↗

Get Hard (2015)

1 mentions · Sean Fennessey▶ 1:25:13IMDb ↗Lb ↗

Ghostbusters (1984)

1 mentions · Sean Fennessey▶ 3:44IMDb ↗Lb ↗

Gremlins (1984)

1 mentions · Sean Fennessey▶ 56:42IMDb ↗Lb ↗

Directors Referenced (3)

Sean Penn

3 mentions · Bill Simmons · Known for Mystic River, 21 Grams, Dead Man Walking▶ 1:19IMDb ↗Lb ↗

John Hughes

2 mentions · Sean Fennessey, Bill Simmons · Known for Planes, Trains & Automobiles, Uncle Buck, The Breakfast Club▶ 13:11IMDb ↗Lb ↗

Cecil B. DeMille

1 mentions · Sean Fennessey · Known for The Ten Commandments, The Greatest Show on Earth, Sunset Boulevard▶ 31:52IMDb ↗Lb ↗

Actors Referenced (26)

Bill Murray

21 mentions · Bill Simmons, Sean Fennessey · Known for Lost in Translation, Rushmore, Moonrise Kingdom▶ 0:59IMDb ↗Lb ↗

Ted Knight

19 mentions · Bill Simmons, Sean Fennessey · Known for Caddyshack▶ 0:59IMDb ↗Lb ↗

Chevy Chase

18 mentions · Sean Fennessey, Bill Simmons · Known for Memoirs of an Invisible Man, Caddyshack, National Lampoon's Vacation▶ 0:59IMDb ↗Lb ↗

Rodney Dangerfield

15 mentions · Bill Simmons, Sean Fennessey · Known for Caddyshack▶ 0:59IMDb ↗Lb ↗

Ty Webb

9 mentions · Bill Simmons, Sean Fennessey▶ 20:21IMDb ↗Lb ↗

Michael O'Keefe

6 mentions · Bill Simmons, Sean Fennessey · Known for Caddyshack, Michael Clayton▶ 18:09IMDb ↗Lb ↗

Kenny Loggins

5 mentions · Sean Fennessey, Bill Simmons · Known for Footloose, Caddyshack, Top Gun▶ 10:23IMDb ↗Lb ↗

Cindy Morgan

4 mentions · Bill Simmons, Sean Fennessey · Known for Caddyshack▶ 40:15IMDb ↗Lb ↗

Jackie Mason

2 mentions · Sean Fennessey, Bill Simmons · Known for The Jerk▶ 1:37:09IMDb ↗Lb ↗

LeBron James

2 mentions · Sean Fennessey▶ 36:11IMDb ↗Lb ↗

Philip Seymour Hoffman

2 mentions · Sean Fennessey▶ 32:03IMDb ↗Lb ↗

Aretha Franklin

1 mentions · Bill Simmons · Known for The Blues Brothers▶ 17:09IMDb ↗Lb ↗

Writers Referenced (2)

Harold Ramis

10 mentions · Bill Simmons, Sean Fennessey · Known for Ghostbusters, Groundhog Day, Stripes▶ 10:35IMDb ↗Lb ↗

Roger Ebert

1 mentions · Bill Simmons▶ 23:27IMDb ↗Lb ↗