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‘Caddyshack’ With Bill Simmons and Sean Fennessey

August 18, 2020 · Caddyshack (1980) · Comedy · Sport · 1:41:33 · ▶ Listen on Spotify

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Who Won the Movie

Bill SimmonsRodney DangerfieldMultiple 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▶ 11:47

Most Rewatchable Scene

Bill SimmonsMultiple 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▶ 25:16

What's Aged the Best

Bill SimmonsMultiple 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▶ 44:26
Sean FennesseyAgrees with Kenny Loggins theme song ('still whips ass'), acknowledges the Noonan phenomenon, and agrees that Judge Smales getting his comeuppance has aged well▶ 50:13

What's Aged the Worst

Bill SimmonsMultiple 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▶ 52:09
Sean FennesseyAgreed 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▶ 56:19

Casting What-Ifs

Bill SimmonsMickey RourkeMickey 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.▶ 1:01:19
Sean FennesseyMickey RourkeAgrees 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.▶ 1:03:04

Joey Pants Award

Bill SimmonsScott ColombyTony Denunzio (Scott Columbo) - the guy from Porky's and Caddyshack who was never really seen again▶ 1:07:53
Sean FennesseyDan ResinDiscussed 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▶ 1:07:35

Apex Mountain

Bill SimmonsMichael O'KeefeMichael 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)▶ 1:14:52
Sean FennesseyMichael O'KeefeMichael O'Keefe - yes, coming off The Great Santini▶ 1:14:39

Picking Nits

Bill SimmonsMultiple 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▶ 1:20:00
Sean FennesseyAgrees 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▶ 1:22:59

Best Quote

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

Probably Unanswerable Questions

Bill SimmonsAsked 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▶ 1:27:57
Sean FennesseyJudge 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▶ 1:28:18

Movies Referenced (24)

Title (year)LinksMentionsMentioned byFirst
The Judge (2014)IMDb ↗Lb ↗10Bill Simmons▶ 51:07
Cinderella (2015)IMDb ↗Lb ↗4Bill Simmons, Sean Fennessey▶ 30:20
Lights Out (2016)IMDb ↗Lb ↗3Bill Simmons▶ 17:09
Groundhog Day (1993)IMDb ↗Lb ↗2Sean Fennessey▶ 3:44
Pump Up the Volume (1990)IMDb ↗Lb ↗2Bill Simmons▶ 1:40:36
The Blues Brothers (1980)IMDb ↗Lb ↗2Sean Fennessey▶ 16:24
Top Gun (1986)IMDb ↗Lb ↗2Bill Simmons, Sean Fennessey▶ 49:36
Alien (1979)IMDb ↗Lb ↗1Bill Simmons▶ 40:09
Beverly Hills Cop (1984)IMDb ↗Lb ↗1Sean Fennessey▶ 16:10
Casablanca (1942)IMDb ↗Lb ↗1Sean Fennessey▶ 9:36
Get Hard (2015)IMDb ↗Lb ↗1Sean Fennessey▶ 1:25:13
Ghostbusters (1984)IMDb ↗Lb ↗1Sean Fennessey▶ 3:44

Directors Referenced (3)

NameLinksMentionsMentioned byKnown ForFirst
Sean PennIMDb ↗Lb ↗3Bill SimmonsMystic River, 21 Grams, Dead Man Walking▶ 1:19
John HughesIMDb ↗Lb ↗2Sean Fennessey, Bill SimmonsPlanes, Trains & Automobiles, Uncle Buck, The Breakfast Club▶ 13:11
Cecil B. DeMilleIMDb ↗Lb ↗1Sean FennesseyThe Greatest Show on Earth, Sunset Boulevard▶ 31:52

Actors Referenced (27)

NameLinksMentionsMentioned byKnown ForFirst
Bill MurrayIMDb ↗Lb ↗21Bill Simmons, Sean FennesseyLost in Translation, Rushmore, Moonrise Kingdom▶ 0:59
Ted KnightIMDb ↗Lb ↗19Bill Simmons, Sean FennesseyCaddyshack▶ 0:59
Chevy ChaseIMDb ↗Lb ↗18Sean Fennessey, Bill SimmonsMemoirs of an Invisible Man, Caddyshack, National Lampoon's Vacation▶ 0:59
Rodney DangerfieldIMDb ↗Lb ↗15Bill Simmons, Sean FennesseyCaddyshack▶ 0:59
Ty WebbIMDb ↗Lb ↗9Bill Simmons, Sean Fennessey▶ 20:21
Michael O'KeefeIMDb ↗Lb ↗6Bill Simmons, Sean FennesseyCaddyshack, Michael Clayton▶ 18:09
Kenny LogginsIMDb ↗Lb ↗5Sean Fennessey, Bill SimmonsFootloose, Caddyshack, Top Gun▶ 10:23
Cindy MorganIMDb ↗Lb ↗4Bill Simmons, Sean FennesseyCaddyshack▶ 40:15
Jackie MasonIMDb ↗Lb ↗2Sean Fennessey, Bill SimmonsThe Jerk▶ 1:37:09
LeBron JamesIMDb ↗Lb ↗2Sean Fennessey▶ 36:11
Philip Seymour HoffmanIMDb ↗Lb ↗2Sean Fennessey▶ 32:03
Rob LowIMDb ↗Lb ↗2Sean Fennessey, Bill Simmons▶ 1:12:10

Writers Referenced (2)

NameLinksMentionsMentioned byKnown ForFirst
Harold RamisIMDb ↗Lb ↗10Bill Simmons, Sean FennesseyGhostbusters, Groundhog Day, Stripes▶ 10:35
Roger EbertIMDb ↗Lb ↗1Bill Simmons▶ 23:27