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‘Tommy Boy’ With Bill Simmons, Sean Fennessey, and Cousin Sal

April 3, 2020 · Tommy Boy (1995) · Adventure · Comedy · 1:28:15

IMDb ↗Letterboxd ↗

Categories

Most Rewatchable Scene

Bill Simmons▶ 31:14Tommy on the boat with Julie Warner - the scene where he talks about his father's death, then gets heckled by kids and she defends him
Cousin Sal▶ 36:03Tommy's first sales meeting where he reenacts the car accident - calls it his favorite and most rewatchable
Sean Fennessey▶ 36:16Tommy's first sales meeting where he reenacts the car accident with the brake pads demonstration

What's Aged the Best

Bill Simmons▶ 46:22Rob Lowe's performance - he's really good in this movie and showed a comedy side that wouldn't have been predicted in the 80s
Cousin Sal▶ 48:58The casting of Bo Derek with Rob Lowe vs Brian Dennehy - the age dynamics and how they nailed that casting
Sean Fennessey▶ 49:38Brian Dennehy's performance - he's overqualified but locked in and willing to go toe to toe with Farley on all the dumb bits

Casting What-Ifs

Bill Simmons▶ 59:39Rob Lowe — Rob Lowe in Richard's role would have been weird; Spade was the right choice over Sandler or Lowe. McConaughey would have been fun in the role. Roseanne Barr not playing Helen was probably a good miss.

Joey Pants Award

Bill Simmons▶ 1:00:59Zach Grenier — Zach Grinier (Tommy's board member with bulgy eyes who was in Fight Club and Curb Your Enthusiasm)
Sean Fennessey▶ 1:01:01Zach Grenier — Zach Grinier - 'He is absolutely the winner of this category, without question'

Dion Waiters Award

Bill Simmons▶ 1:05:50Rob Lowe
Cousin Sal▶ 1:06:08Rob Lowe — Rob Lowe - agreed with the pick
Sean Fennessey▶ 1:05:54Rob Lowe — Rob Lowe - praised his four scenes, especially the cow tipping scene

Half-Assed Internet Research

Bill Simmons▶ 1:12:19Multiple trivia facts including Rob Lowe being uncredited, Farley doing his own stunts, the Spade-Farley altercation over Rob Lowe, Bo Derek's Razzie nomination, both hosts dating Lori Bagley, and original title being 'Billy the Third of Midwestern'
Cousin Sal▶ 1:13:13Added details about Farley being too sick to go out, Farley crushing Spade's tuna sandwich, and 'Rocky Road' as another considered title
Sean Fennessey▶ 1:14:31Liked 'Billy the Third of Midwestern' as a title, calling it 'pretty highfalutin'

Apex Mountain

Bill Simmons▶ 1:14:38Chris Farley — Chris Farley (yes), David Spade (yes, though notes younger generation knows him from Grown Ups), Julie Warner (yes for Tommy Boy), break pads (yes), Holy Shnikes (yes)
Cousin Sal▶ 1:16:31Chris Farley — Holy Shnikes, which Farley took from John Candy in Planes, Trains and Automobiles
Sean Fennessey▶ 1:15:16Julie Warner — Julie Warner's apex was Doc Hollywood due to the emerging from water scene, similar to Bo Derek's moment; also agrees on break pads

Best Quote

Bill Simmons▶ 1:20:46Multiple quotes including 'A lot of people go to college for seven years. I know they're called doctors', 'I'm retarded', 'Did you eat a lot of paint chips as a kid?', and 'I just barfed on an animal'
Cousin Sal▶ 1:21:50I could get a good look at a steak by sticking my head up a bull's ass. But I'd rather take the butcher's word for it.

Probably Unanswerable Questions

Bill Simmons▶ 1:22:19Bo Derek probably killed Tommy Sr. by poisoning him during the wedding reception, and Tommy and Julie Warner's relationship status is unclear - they went on one date but never kissed yet she seems like his girlfriend
Cousin Sal▶ 1:22:43Agrees Bo Derek likely murdered Tommy Sr. and thinks Tommy and Julie Warner could work as a couple long-term despite the unclear nature of their relationship
Sean Fennessey▶ 1:25:07Believes in the possibility of love between Julie Warner and Chris Farley's Tommy, though acknowledges the physical logistics would be terrifying given their size difference

Who Won the Movie

Bill Simmons▶ 1:25:25Chris Farley
Cousin Sal▶ 1:25:51Chris Farley — Agrees with Chris Farley choice and reflects on missing him, noting how effective he would have been at coronavirus PSAs

Movies Referenced (22)

Wayne's World (1992)

7 mentions · Bill Simmons, Sean Fennessey, Cousin Sal▶ 22:02IMDb ↗Lb ↗

Doc Hollywood (1991)

5 mentions · Sean Fennessey, Bill Simmons▶ 1:15:15IMDb ↗Lb ↗

Black Sheep (1996)

4 mentions · Cousin Sal, Bill Simmons▶ 5:58IMDb ↗Lb ↗

Billy Madison (1995)

2 mentions · Bill Simmons▶ 59:31IMDb ↗Lb ↗

Dirty Work (1998)

2 mentions · Bill Simmons▶ 12:37IMDb ↗Lb ↗

Happy Gilmore (1996)

2 mentions · Sean Fennessey▶ 55:23IMDb ↗Lb ↗

A Time to Kill (1996)

1 mentions · Bill Simmons▶ 1:00:06IMDb ↗Lb ↗

Bad Influence (1990)

1 mentions · Bill Simmons▶ 1:08:23IMDb ↗Lb ↗

Cast Away (2000)

1 mentions · Bill Simmons▶ 1:25:32IMDb ↗Lb ↗

Dazed and Confused (1993)

1 mentions · Bill Simmons▶ 1:00:03IMDb ↗Lb ↗

Death of a Salesman (1951)

1 mentions · Sean Fennessey▶ 49:49IMDb ↗Lb ↗

Enemy of the State (1998)

1 mentions · Bill Simmons▶ 1:27:34IMDb ↗Lb ↗

Directors Referenced (1)

Tom Brady

3 mentions · Cousin Sal, Bill Simmons · Known for The Hot Chick▶ 23:56IMDb ↗Lb ↗

Actors Referenced (51)

Chris Farley

84 mentions · Bill Simmons, Cousin Sal, Sean Fennessey · Known for Tommy Boy, Black Sheep▶ 3:34IMDb ↗Lb ↗

Rob Lowe

32 mentions · Bill Simmons, Cousin Sal, Sean Fennessey · Known for St. Elmo's Fire▶ 34:03IMDb ↗Lb ↗

David Spade

30 mentions · Bill Simmons, Cousin Sal, Sean Fennessey · Known for Tommy Boy▶ 4:09IMDb ↗Lb ↗

John Belushi

25 mentions · Bill Simmons, Cousin Sal, Sean Fennessey · Known for National Lampoon's Animal House, The Blues Brothers▶ 7:56IMDb ↗Lb ↗

Bo Derek

15 mentions · Bill Simmons, Cousin Sal, Sean Fennessey · Known for Tommy Boy▶ 34:03IMDb ↗Lb ↗

Julie Warner

15 mentions · Bill Simmons, Sean Fennessey · Known for Tommy Boy, Doc Hollywood▶ 31:18IMDb ↗Lb ↗

Adam Sandler

7 mentions · Bill Simmons, Cousin Sal · Known for Big Daddy, Little Nicky▶ 11:05IMDb ↗Lb ↗

Brian Dennehy

7 mentions · Cousin Sal, Bill Simmons, Sean Fennessey · Known for First Blood▶ 48:30IMDb ↗Lb ↗

Dan Aykroyd

7 mentions · Cousin Sal, Sean Fennessey, Bill Simmons · Known for Ghostbusters▶ 55:35IMDb ↗Lb ↗

Bob Dole

5 mentions · Bill Simmons, Cousin Sal▶ 4:05IMDb ↗Lb ↗

Chris Rock

4 mentions · Bill Simmons, Cousin Sal · Known for Top Five, The Longest Yard▶ 11:15IMDb ↗Lb ↗

Julie Bowen

3 mentions · Sean Fennessey · Known for Happy Gilmore▶ 1:11:40IMDb ↗Lb ↗

Writers Referenced (5)

Roger Ebert

8 mentions · Bill Simmons, Sean Fennessey, Cousin Sal▶ 17:46IMDb ↗Lb ↗

Lorne Michaels

4 mentions · Bill Simmons▶ 16:46IMDb ↗Lb ↗

Bonnie Turner

1 mentions · Cousin Sal▶ 23:56IMDb ↗Lb ↗

Matt Loman

1 mentions · Sean Fennessey▶ 49:51IMDb ↗Lb ↗

Taylor Worst

1 mentions · Bill Simmons▶ 1:13:30IMDb ↗Lb ↗

Cinematographers Referenced (2)

Barry Ackroyd

5 mentions · Bill Simmons, Cousin Sal · Known for The Hurt Locker, Captain Phillips, United 93▶ 56:27IMDb ↗Lb ↗

Michael Grantland

1 mentions · Bill Simmons · Known for The Other Guys▶ 1:07:43IMDb ↗Lb ↗