Billy Madison (1995)
Billy Madison is the 27 year-old son of Bryan Madison, a very rich man who has made his living in the hotel industry. Billy stands to inherit his father's empire, but only if he can make it through all 12 grades, 2 weeks per grade, to prove that he has what it takes to run the family business.
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Added by Hextor · 5 months ago
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🎙️ SYSK Episodes
#092325
Tdhtdhtdhtdhtdh: Sound Effects!
"You're like Billy Madison playing dodge ball in Billy Madison."
— Josh
Josh compares Chuck's laser tag strategy to the dodgeball scene in Billy Madison.
Sep 23, 2025
#072523
Learning a Foreign Language
"It always reminds me of Billy Madison, like smacking that, blocking that shot from that little kid on the playground."
— Josh
Josh references a scene where an adult character blocks a child's basketball shot as a humorous comparison to adults learning faster than children in language acquisition.
Jul 25, 2023
#072322
Selects: What's the misery index?
"PS was in disbelief when Chuck said he had not seen Billy Madison or Happy Gilmore."
A listener expresses disbelief that Chuck hasn't seen this Adam Sandler film, mentioned in the listener mail section.
Jul 23, 2022
#070621
The Sad Story of William James Sidis
"It was basically like Billy Madison."
— Josh
Josh compares William Sidis graduating through primary school in seven months to the movie Billy Madison.
Jul 6, 2021
#032218
How the Framingham Heart Study Works
"You know that one party scene in Billy Madison was filmed at Hearst Castle."
— Josh
Josh mentions that a party scene in Billy Madison was filmed at Hearst Castle during discussion of the Elephant Seal Beach.
Mar 22, 2018
#122817
How the Seven Wonders of the Ancient World Works, Part II
"the original Billy Madison Happy Gilmore role"
— Chuck
Chuck mentions this Adam Sandler comedy when discussing the types of roles Sandler should stick to.
Dec 28, 2017
#072717
A Dry Look at Toilet Paper
"Did you call the bad guy from Billy Madison being the bad guy? Billy, was he in Billy Madison?"
— Josh
Referenced Billy Madison in discussion of Get Out's villain actor.
Jul 27, 2017
#062316
What's the misery index?
"P.S. was in disbelief when Chuck said he had not seen Billy Madison or Happy Gilmore."
A listener expressed disbelief that Chuck had not seen Adam Sandler films Billy Madison and Happy Gilmore.
Jun 23, 2016
#051415
How Pinewood Derbies Work
"His best role, though, seriously was in Billy Madison."
— Chuck
Chuck mentions Bradley Whitford's role in Billy Madison as his best performance.
May 14, 2015
#030812
How Noah's Ark Worked
"And Billy Madison was awesome. Yeah, Billy Madison."
— Chuck
Chuck mentions Billy Madison as another notable role of Darren McGavin's career.
Mar 8, 2012
Cast
Adam Sandler
Billy Madison
Bradley Whitford
Eric Gordon
Josh Mostel
Principal Max Anderson
Bridgette Wilson
Veronica Vaughn
Darren McGavin
Brian Madison
Norm Macdonald
Frank
Mark Beltzman
Jack
Larry Hankin
Carl Alphonse
Theresa Merritt
Juanita
Dina Platias
Miss Lippy
Hrant Alianak
Pete
V
Vincent Marino
Cook
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