This Adam Sandler movie trivia quiz has 180 free questions with answers and runs through three decades of Sandler films: the 1990s cult comedies (Billy Madison, Happy Gilmore, The Waterboy, The Wedding Singer, Big Daddy), the 2000s hits (Mr. Deeds, Anger Management, 50 First Dates, Click, Grown Ups), the Netflix era (Murder Mystery, Hubie Halloween, Happy Gilmore 2) and the dramatic turns critics loved, from Punch-Drunk Love to Uncut Gems, Hustle and Spaceman. A Benchwarmers trivia round covers the 2006 Happy Madison baseball comedy Sandler produced: the Schneider-Spade-Heder trio, Jon Lovitz's billionaire, Reggie Jackson's cameo, the Pizza Hut finale and its box-office record. Expect plot details, casting stories, box-office facts and Razzie history. About a third of the questions are easy enough for anyone who has seen a couple of Sandler movies, a third are medium, and the rest reward the fan who knows the name of the alligator, the sandwich chain and the fictional amnesia. Every answer has been checked against a primary source, and each question links to the page that confirms it.
30 of 180 questions with answers and explanations. Play the quiz
Q 01In Happy Gilmore, what sport was Happy failing at before he discovered golf?
Ice hockey
His slapshot swing could drive a ball 400 yards.
Q 02Happy Gilmore takes up golf to save his grandmother's house from which creditor?
The IRS
Grandma Anna owed $270,000 in back taxes and had 90 days to pay.
Q 03Happy's mentor Chubbs Peterson lost his hand to what?
An alligator
Happy later kills the one-eyed gator that did it.
Q 04Which game-show host brawls with Happy at a pro-am and shared an MTV Movie Award for Best Fight?
Bob Barker
Barker was still hosting The Price Is Right when the film came out.
Q 05Which sandwich chain gives Happy Gilmore the endorsement deal that lets him buy back Grandma's house?
Subway
Roger Ebert counted more than a dozen brands placed in the film.
Q 06Who plays Happy's arrogant rival Shooter McGavin?
Christopher McDonald
Ben Stiller has an uncredited role as an abusive nursing-home orderly.
Q 07Happy Gilmore's 2025 sequel skipped cinemas for which streaming service?
Netflix
Its caddy from the first film was retroactively revealed to be golfer Will Zalatoris.
Q 08In Billy Madison, how long must Billy spend in each grade to earn his father's company?
Two weeks
He is a 27-year-old heir to a Fortune 500 hotel chain.
Q 09Which comedian made his feature-film debut in Billy Madison?
Norm Macdonald
Farley plays the erratic bus driver, reportedly after six espresso shots.
Q 10Billy Madison's school principal Max Anderson was once a pro wrestler known as what?
The Revolting Blob
Eric Gordon uses the secret to blackmail him.
Q 11How does Billy Madison propose to settle who inherits Madison Hotels?
An academic decathlon
Director Tamra Davis said the real dodgeball scene left the child actors crying.
Q 12Which director made Billy Madison?
Tamra Davis
Sandler co-wrote it with his longtime partner Tim Herlihy.
Q 13In The Waterboy, Bobby Boucher's only means of transportation is what?
A riding lawnmower
He and Vicki ride off on it at the end of the film.
Bobby Boucher believes his father died of dehydration where?
Q 21The Wedding Singer was Sandler's first film with which co-star, later of 50 First Dates and Blended?
Drew Barrymore
Blended was also directed by Wedding Singer director Frank Coraci.
Q 22In Big Daddy, Sonny Koufax lives comfortably off what?
A $200,000 accident settlement
He works one day a week as a toll booth attendant.
Q 23Which twin brothers shared the role of Julian in Big Daddy?
Dylan and Cole Sprouse
They were five years old at the time.
The Sahara
The story turns out to be a fib from his overprotective Mama.
Q 15Who plays Bobby Boucher's fiercely religious mother, Helen, in The Waterboy?
Kathy Bates
Her agent did not want her to take the part and she initially threw the script away.
Q 16The Mud Dogs' season in The Waterboy ends at which New Year's Day game?
The Bourbon Bowl
They win 30-27 and Bobby is named MVP.
Q 17Which Waterboy character is often compared to real LSU coach Ed Orgeron?
Farmer Fran
The comparison rests on Orgeron's Cajun roots and accent.
Q 18In what year is The Wedding Singer set?
1985
The soundtrack ranges from the Buggles to Nena's '99 Luftballons'.
Q 19Which rock star helps Robbie serenade Julia on the plane in The Wedding Singer?
Billy Idol
The song Robbie sings is 'Grow Old with You', co-written by Sandler and Tim Herlihy.
Q 20The Wedding Singer was later adapted into what?
A Broadway musical
It opened in April 2006 and closed that New Year's Eve.
Q 24Sonny's roommate Kevin in Big Daddy is played by which future Daily Show host?
Jon Stewart
His fiancée Corinne is mocked relentlessly for her old Hooters job.
Q 25Big Daddy earned Sandler which dubious honour?
A Razzie for Worst Actor
The film was still a hit, grossing $234.8 million.
Q 26In Punch-Drunk Love, Barry Egan buys huge quantities of what to earn frequent-flyer miles?
Pudding
It was inspired by a real man who amassed over a million miles from Healthy Choice pudding.
Q 27What instrument does Barry find abandoned in the street in Punch-Drunk Love?
A harmonium
Jon Brion's score uses no harmonium beyond the notes Sandler plays himself.
Q 28Which director wrote Punch-Drunk Love specifically for Sandler?
Paul Thomas Anderson
He won Best Director at Cannes for it in 2002.
Q 29What does Barry Egan's company sell in Punch-Drunk Love?
Novelty toilet plungers
Philip Seymour Hoffman plays the mattress-store owner running a phone-sex scam.
Q 30Lucy in 50 First Dates suffers from a fictional amnesia named what?
Goldfield's syndrome
She remembers everything up until the night before her car crash.