Top Five Adam Sandler Movies and ‘Hustle’

‘Hustle’new on Netflix

Hustle 2022

Directed by Jeremiah Zagar, written by Taylor Materne and Will Fetters. Sandler plays Stanley Sugerman, a down-on-his-luck 76ers scout who finds a streetball phenom in Spain, played by real NBA player Juancho Hernangomez, and brings him to Philadelphia to try out for the Sixers. Rob calls it a 'soft Happy Gilmore reboot,' pointing to Sandler's scarred hand echoing Carl Weathers' wooden hand as Chubbs, and to real NBA players filling the cast: Trae Young, Khris Middleton, Aaron Gordon, Seth Curry, Matisse Thybulle, Tobias Harris, Doc Rivers, and Timberwolves star Anthony Edwards as the villain, playing a fictional rival rather than himself. Queen Latifah plays Sandler's wife. Both hosts land on 'not his best work on Netflix, but far from his worst.' No Sandler mugging or singing; it's played straight as a drama.

The Sandler TimelineSNL through the Netflix years

Coneheads 1993

A Lorne Michaels production Sandler appeared in while still on 'Saturday Night Live,' ahead of his own leading roles.

Airheads 1994

Sandler in a supporting role as a band's dim-witted drummer. Both hosts call it the platonic Sean-and-Rob movie for its music-nerd trivia (guessing which Van Halen lineup).

The Waterboy 1998

Sandler's biggest hit to that point, bigger than 'Billy Madison' and 'Happy Gilmore' combined, which Sean partly holds against it since he found those two funnier. Henry Winkler co-stars as the coach. Rob rewatched it and found it dragged.

Big Daddy 1999

Did well commercially; Sean preferred it to 'The Waterboy.'

Little Nicky 2000

Cited as the point where the run of dumb comedies stumbled, ahead of Sandler's early dramatic pivot.

Spanglish 2004

Closes out Sandler's early-2000s stretch. Sean calls it 'not a problematic film, just a problem as a film' given the talent involved.

The Longest Yard 2005

Part of the run into 'Click,' the film Sean marks as the start of Sandler's recurring good-dad-on-screen roles.

Click 2006

The film Sean points to as the first time Sandler played a dad on screen, a role he'd return to for the rest of his career.

The Ridiculous 6 2015

Sandler's first Netflix movie. Sean argues it 'arrived poorly' (there was a real-world revolt among Native American extras over its portrayal of Native Americans), but defends the 'sweet hog rock' sight gag as worth the runtime on its own.

Adam Sandler: 100% Fresh 2018

Rob's favorite thing Sandler has ever made. He saw it live at the OSU basketball arena. Highlights include the songs 'My Uber Driver Smells Bad' and 'Phone Wallet Keys,' and a Chris Farley tribute song Rob calls 'beautiful' and 'tear-jerking,' which Sandler also performed on an SNL hosting gig.

Hotel Transylvania 2012

Sean, as a parent, singles out the franchise (Sandler voices Dracula opposite Selena Gomez and Andy Samberg) as some of Sandler's most purely enjoyable recent work, and probably his biggest box-office draw as a series.

Rob's Top Five Sandlerranked best to worst

No. 1

Happy Gilmore 1996

No. 1. Rewatched it that morning and declared it holds up completely: 'a better movie than Punch-Drunk Love, better than The Godfather Part Two,' citing the Bob Barker fight as the funniest three beats in a row he's seen in a movie. Christopher McDonald's Shooter McGavin is, for Rob, one of the best comedy villains ever.

No. 2

Punch-Drunk Love 2002

No. 2. Rob's first real experience of a comedian he loved going serious. He rewatched Jon Brion's score-driven tension and Sandler's rage-then-mumble register and calls it beautifully made, though it never fully clicks for him emotionally the way it does for Sean.

No. 3

The Meyerowitz Stories 2017

No. 3. Rob's favorite Sandler scene of all is here: Sandler playing piano and singing with his on-screen daughter, Grace Van Patten, on a song her character wrote at nine. He calls the performance the perfect balance of comedic and dramatic Sandler.

No. 4

Uncut Gems 2019

No. 4. Rob respects it more than he likes it. He calls it 'a movie engineered to stress me the fuck out,' compounded by a bathroom-break mishap that made him miss the first ten minutes and rewatch the whole thing. He praises Sandler's chemistry with Julia Fox and Kevin Garnett but says it's tailor-made for him not to enjoy.

No. 5

The Wedding Singer 1998

No. 5. Rob's pick for the rom-com slot. He calls Sandler and Drew Barrymore one of the best-matched romantic-comedy pairings ever, singling out the plane scene where Sandler sings to her with Billy Idol looking on.

Sean's Top Five Sandlerranked best to worst

No. 1

Punch-Drunk Love 2002

No. 1. Sean's favorite Sandler performance and one of his favorite movies, period. He loves the chemistry with Emily Watson and the surrounding cast (Mary Lynn Rajskub, Luis Guzman, Robert Smigel, and Philip Seymour Hoffman as Dean Trumbell), and credits Paul Thomas Anderson with proving Sandler could carry a serious role by stripping the jokes but keeping his head-of-steam energy.

No. 2

Billy Madison 1995

No. 2. Formative for Sean, who saw it in theaters at 12. He calls out the supporting cast (Bradley Whitford as the villain, Norm Macdonald as Billy's buddy Frank, Bridgette Wilson as love interest Veronica Vaughn, and Darren McGavin as Billy's father) and the 'if peeing your pants is cool, I'm Miles Davis' line as one of the funniest ever delivered on camera.

No. 3

Uncut Gems 2019

No. 3. Sean calls Howard Ratner one of the most fascinating and tragic characters Sandler has ever played, made harder by how much of the film rests on him opposite non-professional actors like Julia Fox and Kevin Garnett.

No. 4

Happy Gilmore 1996

No. 4. Sean co-hosted a Rewatchables episode on it with Ben and Josh Safdie. He calls it the perfect fusion of manic, screaming Sandler and sweet, vulnerable Sandler, citing the scene where Happy screams at his ex-girlfriend through an intercom, then tries to win her back.

No. 5

The Meyerowitz Stories 2017

No. 5. Sean calls it on the cusp of his favorite Sandler dramatic performance: no mugging or singing, and a quiet, complicated relationship with Dustin Hoffman's character as his father, capped by a MoMA sequence Sean singles out.

Honorable mentions

Billy Madison 1995

Rob's own runner-up. He calls leaving it off his top five 'a travesty' and says it easily could have been his No. 1 or 2, but he bumped it in favor of Happy Gilmore to better represent the full Sandler range.

Funny People 2009

Rob's honorable mention: a Judd Apatow dramedy where Sandler plays a version of himself reckoning with the wreckage of his fame. Not Sandler's best movie or performance, Rob says, but proof he could hang dramatically before Punch-Drunk Love reset expectations, and a precursor to the Netflix era that followed soon after. Eminem's cameo, yelling at Ray Romano, is the funniest thing in it for Rob.

Also mentioned raised along the way

Sandler's other Netflix and studio films Mr. DeedsAnger Management50 First DatesGrown UpsGrandma's BoyI Now Pronounce You Chuck & LarryMurder MysterySandy WexlerHubie Halloween

In passing Wayne's WorldMan on the MoonThe Love GuruLost in TranslationMotherless BrooklynMarriage StoryBoogie NightsMagnoliaKnocked UpWhite NoiseSpaceballs

Not films filtered out: TV, games, ads

TV Saturday Night LiveBarryHouse of Cards

Ads Whole FoodsCarvanaPeyronie's Disease (TalkAboutPD.com)Boar's HeadWhite Claw

Games FIFA World Cup Launch Edition

Cross-promo 60 Songs That Explain the 90s