Adam Sandler Movies
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This Adam Sandler movie trivia quiz has 176 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 176 questions with answers and explanations. Play the quiz
Q 01In Happy Gilmore, what sport was Happy failing at before he discovered golf?
Ice hockey
Happy Gilmore was a failed ice hockey player; the slapshot swing he brought to the driving range sent balls more than 400 yards.
Q 02Happy Gilmore takes up golf to save his grandmother's house from which creditor?
The IRS
The IRS seized Grandma Anna's house over $270,000 in unpaid back taxes, giving Happy 90 days to raise the money.
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 signs Happy Gilmore to an endorsement deal in the film?
Subway
Subway signs Happy as its spokesman once he becomes a tour sensation; he films a sub commercial and uses the money to bid on Grandma's house.
Q 06Who plays Happy's arrogant rival Shooter McGavin?
Christopher McDonald
Christopher McDonald plays Shooter McGavin, the smug tour pro who taunts Happy and buys Grandma's house at auction to spite him.
Q 07Happy Gilmore's 2025 sequel skipped cinemas for which streaming service?
Netflix
Happy Gilmore 2 premiered on Netflix on July 25, 2025, almost thirty years after the original, with Sandler back as Happy.
Q 08In Billy Madison, how long must Billy spend in each grade to earn his father's company?
Two weeks
Billy must pass all twelve grades in 24 weeks, two weeks per grade, to inherit Madison Hotels instead of Eric Gordon.
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
Principal Anderson wrestled as The Revolting Blob, and Eric Gordon uses that past to blackmail him into claiming Billy cheated.
Q 11How does Billy Madison propose to settle who inherits Madison Hotels?
An academic decathlon
Billy challenges Eric Gordon to an academic decathlon, a contest of school subjects with a Jeopardy-style final round, to decide who inherits Madison Hotels.
Q 12Which director made Billy Madison?
Tamra Davis
Tamra Davis directed Billy Madison (1995); Sandler co-wrote the script with his longtime partner Tim Herlihy.
Q 13In The Waterboy, Bobby Boucher's only means of transportation is what?
A riding lawnmower
Bobby's only ride is a riding lawnmower; he and Vicki Vallencourt drive off on it after their wedding at the end of the film.
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
Twins Dylan and Cole Sprouse, born in 1992, alternated as Julian, the usual way a child role stays within daily work-hour limits.
Q 14Bobby Boucher believes his father died of dehydration where?
The Sahara
Mama told Bobby his father died of dehydration in the Sahara Desert; Roberto Boucher later turns up alive, having simply walked out on the family.
Q 15Who plays Bobby Boucher's fiercely religious mother, Helen, in The Waterboy?
Kathy Bates
Kathy Bates, an Oscar winner for Misery, plays Mama Boucher, who blames football, college and girls on 'the devil'.
Q 16The Mud Dogs' season in The Waterboy ends at which New Year's Day game?
The Bourbon Bowl
The Mud Dogs reach the Bourbon Bowl on New Year's Day and beat Red Beaulieu's Louisiana Cougars on Bobby's last-play touchdown.
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 Wedding Singer is set in 1985; its Culture Club haircuts, Miami Vice jackets and Nena's '99 Luftballons' fix it in the mid-eighties.
Q 19Which rock star helps Robbie serenade Julia on the plane in The Wedding Singer?
Billy Idol
Billy Idol, playing himself in first class, rallies the cabin so Robbie can sing 'Grow Old with You', co-written by Sandler and Tim Herlihy.
Q 20The Wedding Singer was later adapted into what?
A Broadway musical
The Wedding Singer became a Broadway musical that opened at the Al Hirschfeld Theatre in April 2006, earned a Best Musical Tony nomination, and closed that New Year's Eve.
Q 24Sonny's lawyer roommate Kevin in Big Daddy is played by which Daily Show host?
Jon Stewart
Jon Stewart plays Kevin Gerrity, whose fiancée Corinne is mocked for her Hooters past; Stewart had taken over The Daily Show in January 1999, months before the film opened.
Q 25Big Daddy earned Sandler which dubious honour?
A Razzie for Worst Actor
Sandler took the 1999 Razzie for Worst Actor for Big Daddy, which nonetheless grossed $234.8 million worldwide.
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
Barry finds a harmonium dumped on the street outside his warehouse after a car crash; he carries it inside and plays it throughout the film.
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
Barry runs a small business selling novelty toilet plungers from a Los Angeles warehouse; the phone-sex scam is run out of Dean Trumbell's mattress store.
Q 30Lucy in 50 First Dates suffers from a fictional amnesia named what?
Goldfield's syndrome
Lucy has Goldfield's syndrome, a fictional condition that erases each day's memories overnight, so she wakes every morning believing it is the day of her crash.