It’s been 29 years since “Happy Gilmore” first teed off — and now, one of Adam Sandler’s most iconic characters is back for round two. “Happy Gilmore 2” officially dropped on Netflix today, reuniting fans with the hot-tempered, hockey-loving golf prodigy who forever changed how we look at mini-golf and aggression on the green.
To celebrate the long-awaited sequel, we’re revisiting Sandler’s best movies — not necessarily his biggest hits or most critically acclaimed, but the ones that defined his career and cemented his legacy as a comedy powerhouse, romantic lead, and, at times, a surprisingly brilliant dramatic actor. Here’s a chronological look at Sandler’s greatest hits — a filmography that’s anything but boring.
1. “Billy Madison” (1995)
The movie that launched the Sandlerverse. In “Billy Madison”, Sandler plays the spoiled man-child heir to a hotel empire who’s forced to redo grades 1–12 to prove he’s ready to take over the family business. The film is outrageous, absurd, and proudly juvenile — exactly the kind of offbeat energy that defined early Sandler. With flaming dog poop, penguin hallucinations, and “O’Doyle rules!” echoing through pop culture, this was the moment the world realized Sandler wasn’t just another SNL alum — he was a brand.
2. “Happy Gilmore” (1996)
If “Billy Madison” was the spark, “Happy Gilmore” was the explosion. Sandler’s performance as the rage-filled hockey reject who discovers he has a killer golf swing is one of his most beloved roles. With help from a one-handed mentor, a smug rival, and the best golf-fight scene in movie history (hello, Bob Barker), “Happy Gilmore” became a sports-comedy classic. It was also the moment Sandler perfected his blend of lowbrow humor, explosive emotion, and genuine underdog appeal.
3. “The Wedding Singer” (1998)
Sandler’s first real romantic comedy — and it worked like a charm. Playing Robbie Hart, a heartbroken wedding singer in 1985 New Jersey, he brings sweetness, awkwardness, and a killer 80s soundtrack to a rom-com that remains one of his most loved. His chemistry with Drew Barrymore is undeniable, kicking off a pairing that would become one of Hollywood’s most charming duos. It’s funny, nostalgic, and sneakily heartfelt — a turning point that showed Sandler could do more than just scream.
4. “The Waterboy” (1998)
Bobby Boucher may speak softly, but he hits hard — and this movie did too. “The Waterboy” was a massive box office success, with Sandler playing a sheltered, stuttering waterboy-turned-football-phenom. The Cajun accents, weird mama quotes, and over-the-top football action made it a favorite among fans who love Sandler at his most absurd. At its core, though, it’s another classic Sandler underdog story — a misfit with a heart of gold who just wants to make his mama proud.
5. “Big Daddy” (1999)
In one of his more emotionally grounded roles, Sandler plays Sonny Koufax, a man-child who unexpectedly ends up raising a five-year-old boy. While the movie is full of laughs and potty humor (literally), it also showcases Sandler’s ability to tug at the heartstrings. “Big Daddy” balances silly and sincere better than most of his early work and became one of his highest-grossing comedies of the 1990s. It’s a reminder that beneath the chaos, Sandler could actually act — and carry a movie with more than just jokes.
6. “Punch-Drunk Love” (2002)
Paul Thomas Anderson saw something in Sandler that few others did — and “Punch-Drunk Love” proved him right. As Barry Egan, a lonely, emotionally volatile novelty supplier, Sandler delivers a performance that’s uncomfortable, tender, and electric. It was his first true foray into dramatic territory, earning him rave reviews and reshaping his reputation. The movie is strange and stylized, but it gave Sandler serious indie cred — and showed that he was capable of greatness far beyond fart jokes.
7. “50 First Dates” (2004)
Reuniting with Drew Barrymore, Sandler plays a charming guy who falls for a woman with short-term memory loss. Every day, he has to make her fall in love with him all over again — and somehow, it works. Set against the backdrop of sunny Hawaii, “50 First Dates” blends goofy humor with genuine sweetness. It’s one of Sandler’s most rewatchable films and features one of his most romantic performances. Their chemistry is magic, and the emotional core hits harder than you’d expect.
8. “Click” (2006)
“Click” begins like another high-concept Sandler comedy — what if you had a remote control that could pause, rewind, and fast-forward life? But what starts as a goofy setup quickly evolves into a surprisingly emotional story about the cost of skipping through life. Sandler’s performance balances comedy and drama beautifully, particularly in the film’s final act. It’s a rare movie that makes you laugh and then hits you with an existential crisis. One of his more underrated entries — and one that holds up.
9. “Grown Ups” (2010)
Sandler reunites with his comedy friends — Chris Rock, Kevin James, David Spade, and Rob Schneider — for this nostalgic comedy about childhood friends reconnecting as adults. It’s less about plot and more about vibes: dad jokes, lake houses, and backyard basketball games. While critics weren’t kind, Grown Ups was a commercial hit and marked the beginning of Sandler’s “hangout movie” era. It’s dumb comfort food — and that’s exactly why so many people love it.
10. “Just Go With It” (2011)
A crowd-pleasing rom-com that leans into mistaken identities, fake relationships, and gorgeous Hawaiian scenery. Sandler stars opposite Jennifer Aniston in this story about a plastic surgeon who ropes his assistant into pretending to be his soon-to-be-divorced wife to win over another woman. As the plan spirals out of control, genuine feelings (of course) start to emerge. It’s silly, predictable, and undeniably fun — and Sandler and Aniston’s chemistry makes it work. Not a critic favorite, but definitely a fan favorite.
11. “Hotel Transylvania” (2012)
Sandler found animated success as the voice of Count Dracula in “Hotel Transylvania”, a kid-friendly comedy about a hotel for monsters. His over-the-top performance, paired with a cast of comedy all-stars, helped the film become a massive hit — spawning three sequels and cementing the franchise as one of Sony Animation’s most profitable. While Sandler only voiced Dracula for the first three films, the “Hotel Transylvania” series proved his appeal extended to family audiences, turning him into a Halloween-season staple for a whole new generation.
12. “Murder Mystery” (2019)
In this Netflix original, Sandler plays a New York cop who takes his wife (Jennifer Aniston) on a long-overdue European vacation — only for the couple to get caught up in a whodunit involving billionaires, yachts, and murder. It’s part comedy, part Agatha Christie send-up, and surprisingly fun. Sandler and Aniston are great together, and the movie’s fast pace and globe-trotting energy helped make it one of Netflix’s most-watched titles. Not prestige, but definitely a hit.
13. “Uncut Gems” (2019)
Sandler’s most intense performance yet. As Howard Ratner, a compulsive gambler and jewelry dealer in over his head, Sandler is mesmerizing — manic, desperate, and impossible to look away from. Directed by the Safdie Brothers, “Uncut Gems” is a high-stakes thriller that moves at breakneck speed and never lets up. Critics and fans were blown away, and while the Oscar snub still stings, the film redefined Sandler’s potential as a dramatic actor. A modern classic — and easily one of his best.
14. “Hustle” (2022)
In “Hustle”, Sandler plays Stanley Sugerman, a down-on-his-luck NBA scout who discovers a talented player overseas and risks everything to get him to the league. It’s a heartfelt underdog story wrapped in the glitz of pro basketball, with real-life NBA stars and a gritty Philly backdrop. Sandler dials it back here, offering a grounded, moving performance that reminds you how much heart he brings to the screen when he’s not playing for laughs. A slam dunk for Sandler’s more serious fans.
15. “You Are So Not Invited to My Bat Mitzvah” (2023)
Starring his real-life daughters Sadie and Sunny Sandler, this Netflix hit is a Gen Z coming-of-age comedy with surprising depth and authenticity. Sandler plays the supportive (and occasionally clueless) dad as his daughter navigates friendship fallouts, crushes, and the chaos of middle school in the lead-up to her bat mitzvah. While Sandler takes a backseat here, the film was praised for its genuine heart and relatability. A fresh chapter in his family-focused filmography — and a win for the next generation.
Adam Sandler’s career spans decades, genres, and an impressive number of Hawaiian vacations. From his earliest man-child roles to his powerful dramatic turns, he’s constantly reinvented himself while staying true to what fans love: humor, heart, and unpredictability. With “Happy Gilmore 2” reminding us just how far he’s come — and how much fun he still is to watch — it’s clear that Sandler’s legacy is still going strong. Whether you prefer your Sandler loud and chaotic or quiet and soulful, there’s no denying: the guy’s got range. “Happy Gilmore 2” is streaming on Netflix.
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