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Tommy Boy poster

Tommy Boy

1995 film

Bill Simmons · Sean Fennessey · Cousin Sal

Aired April 3, 2020

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Caddyshack The Rewatchables
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Caddyshack

Casting What-Ifs

Mickey Rourke as Danny; Michelle Pfeiffer as Lacey; Bo Derek as Lacey; Don Rickles as Al; Pink Floyd for the music

In the discussion (9)
Approx. transcript time · 01:00:55Read transcript
  • Mickey Rourke was the other final candidate for Danny; they correctly decided he was not funny enough.
  • Michael O'Keefe is good: a great golf swing, and he can hang on screen with Chevy Chase at his funniest.
  • Rourke on that era's cocaine-fueled set would have been ugly; Danny is good when Smales tries to hit him with the golf club.
  • Michelle Pfeiffer reportedly turned down Lacey because she did not want to be naked; she could have pulled it off, though she never played a character that frisky.
  • Pfeiffer and Rourke as Lacey and Danny would be a different movie, an Adrian Line erotic thriller; Rourke would compete with Ty, and O'Keefe landing Lacey should feel like a stretch.
  • Producer Peters is said to claim he had Bo Derek for Lacey before 10 and Ramis rejected it; Lacey is assumed to be about 25 and Danny about 17 or 18.
  • These movies shifted American comedy from a Jewish writing tradition toward Irish Catholic voices; Danny's eight-kid family is loosely based on the Murray family, and the young caddy landing Lacey set a template.
  • Don Rickles was considered for Al; he is judged too mean and perhaps better as Judge Smales.
  • Pink Floyd was wanted for the music and declined, thankfully; Ramis's left-of-center interests like Zen Buddhism are noted, and Kenny Loggins came through instead.
Tommy Boy poster
Tommy Boy

Probably Unanswerable Questions

Did Bo Derek's character kill Tommy Sr.?; Were Tommy and Michelle ever a couple?; How do their next six months play out?

In the discussion (4)
Approx. transcript time · 01:21:58Read transcript
  • Did Bo Derek's character kill Tommy Sr., who died at the wedding reception? A spiked drink or toxicology report reveal is suggested, and her ending up with Zelensky is bothersome.
  • Were Tommy and Julie Warner's character dating? They had one date, never kissed, and she nearly left him.
  • Asked about the next six months, a story follows about Jimmy's shelved ABC upfronts parody 'Fat Guy with a Beautiful Wife'; the couple could last. — Cousin Sal
  • The boat could last; love between the two is possible. — Sean Fennessey
Tommy Boy poster
Tommy Boy

Half-Assed Internet Research

Lowe uncredited; Farley's own stunts; Spade-Farley set altercation; Bo Derek's Razzie nomination; the pool actress dating both stars; alternate titles

In the discussion (6)
Approx. transcript time · 01:12:12Read transcript
  • The hosts report Lowe is uncredited; filming The Stand, he felt weird about another movie but did it because he loved Farley; Farley did his own stunts.
  • They relay Spade's story: after Spade drank with Lowe, a jealous Farley kept needling him, Spade threw a Diet Coke, Farley threw him against a wall and down stairs, and Spade walked off; they often communicated through the director.
  • Another version says Farley was too sick to go out, was upset when they went without him, and crushed Spade's tuna sandwich.
  • Bo Derek was reportedly nominated for a Razzie for Worst Supporting Actress.
  • The hosts say the woman in the pool was Lori Bagley, whom both Spade and Farley later dated, causing tension on Black Sheep.
  • They report the working title Billy the Third: A Midwestern was changed because of Billy Madison, with Fat Chance, XL and Rocky Road also considered; Tommy Boy is called the perfect name.
In the discussion (5)
Approx. transcript time · 01:10:09Read transcript
  • Phoebe Cates replaces Bo Derek, a nostalgia pick echoing her Fast Times pool scene and a far better actress than Derek, called abysmal.
  • Without Bo Derek the '10' joke is lost.
  • Julie Warner had been written down but the size disparity is judged worth keeping.
  • A question is floated about swapping Julie Warner for 1995-era Julie Bowen after the Happy Gilmore episode.
  • Cates would have been only 32 in 1995, much closer to Tommy's age; agreed as a fair point.
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Tommy Boy

What’s Aged the Worst?

Sandusky, Ohio setting; Bo Derek stunt casting; Flashdance jokes; sneaking onto a plane as flight attendants; Herbie Hancock joke; rushed brake-pad reversal

In the discussion (10)
Approx. transcript time · 00:51:43Read transcript
  • The Sandusky, Ohio setting is a tough beat that jumps off the screen; the sign and a few spoken mentions could have been changed, as films have done with the Twin Towers.
  • Bo Derek's stunt casting was a big deal in 1995, when she had been like Marilyn Monroe for two years; the equivalent now would be a long-absent Britney Spears, and it no longer translates.
  • Jokes about Flashdance have become progressively less funny; producer Craig is joked not to know what Flashdance is.
  • Sneaking onto a plane as flight attendants is impossible post-9/11; where they were flying from and to is unclear.
  • Too few cameos from the SNL universe is raised, but rebutted: not overloading it makes a better, weirdly sincere movie, and Aykroyd's part drives the story.
  • The Herbie Hancock joke is lost on kids who did not get it. — Cousin Sal
  • Unsure about Aykroyd's character, with a Coneheads voice and a Mel Kuyper Jr. look, the country-club lunch invite at the end, and the finale where a presumed robber with flares gets to a camera crew.
  • Everyone watching local news during a workday and a fake bomb being shrugged off are nitpicked, but it's a comedy.
  • After the whole road trip to sell brake pads, the reversal back in Sandusky happens too quickly to process. — Sean Fennessey
  • A reply adds that drunk Lowe presses two buttons on a computer and everything goes to hell immediately.
Tommy Boy poster
Tommy Boy

What’s Aged the Best?

Opening credits; 'Luke, I'm your father' fan gag; Callahan family portraits; Rob Lowe's performance; the board-meeting old lady; Tommy and Richard singing; the bees gimmick; Spade's hair jokes; the lost-virginity speech; Brian Dennehy

In the discussion (7)
Approx. transcript time · 00:45:45Read transcript
  • The opening credits, the 'Luke, I'm your father' bit with the fan, and the Callahan family portraits with Farley in drag hold up as subtle comedy.
  • Rob Lowe's performance has aged best; he was good in anything SNL adjacent, a comedy side unpredictable in the 1980s.
  • Also listed: the old lady in the board meeting, Tommy and Richard singing, the bees gimmick, the jokes acknowledging Spade's weird hair, and the speech line about losing his virginity to R.T.'s daughter.
  • Bo Derek seemed past her prime then though she was only 39, with Lowe, Farley and Spade 31; pairing her with Dennehy, 57, was accepted but kissing Lowe as a supposed son was strange; the casting is still called nailed.
  • Her haircut is flagged as aged the worst for making her look older, like Alice from The Brady Bunch.
  • Dennehy is incredible and overqualified, a stage legend whose Death of a Salesman history makes him a callback great salesman; serious actors going toe to toe with the bits add credibility, and he is a dead ringer for Farley. — Sean Fennessey
  • An anecdote: interviewing Dennehy in Winnipeg in 2001 in brutal cold for an ESPN Bobby Knight TV movie, he got choked up about Farley; his IMDb has a lot of wins though he never became famous-famous.
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