The Golden Age of Adam Sandler

Seven Adam Sandler movies which are actually worth watching.

Adam Sandler has become, for many, a name associated with atrocious film making. From his lackluster Grown Ups films to the wretched Jack and Jill, Sandler’s films have consistently fallen short. However, believe it or not, there was a time when Sandler was considered to be one of the funniest men in Hollywood. And if you look way (waaaaaay) back, there are a plethora of rather enjoyable films which have aged quite well.

1. Airheads (1994)

“We’re down, man, Hendrix was God.”


While this can’t really be considered an “Adam Sandler movie,” Sandler certainly shines as the bumbling, ignorant sidekick, Pip, alongside leading man Brendan Fraser and the always spectacular Steve Buscemi. Airheads tells the story of three aspiring musicians who hold a radio station hostage with squirt guns. This is a wildly entertaining movie and a hilarious window into ’90’s pop culture.

2. Billy Madison (1995)

“Chlorophyll? More like BOREophyll!”


While I have my quarrels with this film, and I believe it to be the weakest on this list, there is no denying the iconography Billy Madison has had on Sandler’s career. It tells the story of a rich high school dropout who attempts to return to grade school in order to prove to his father that he has what it takes to run the family company. This was, without a doubt, the film that launched Sandler’s career. It is full of great one-liners and classic Sandler stupid comedy. However, glimmers of his demise are definitely evident in this movie.

3. Happy Gilmore (1996)

“You eat pieces of shit for breakfast?”


Perhaps the most beloved film on this list is Sandler’s golfing extravaganza, Happy Gilmore. A failed hockey player tries his hand at golf and finds great success, despite his unprofessional demeanor and the unconventional crowds he draws as he rises to fame. This is Sandler’s funniest movie. To this day I still find myself quoting it with my friends. Sandler’s brewing rage is a stroke of comedic genius opposite a fantastic supporting cast which includes Carl Weathers, Julie Bowen, and the fantastic Christopher McDonald as Shooter McGavin. A must see.

4. The Wedding Singer (1998)

“Sir, one more outburst, I will strangle you with my microphone wire.”


Sandler’s first attempt at a Romantic Comedy opposite Drew Barrymore is a hilariously refreshing entry into a sorry and unoriginal genre. A Wedding Singer falls in love with a beautiful bride-to-be. As he helps her plan her wedding to her typically douchebag fiancé, she discovers she might be marrying the wrong man. Despite all of its clichés, Sandler brings a charming comedic performance to this romantic ’80’s homage. 

5. Big Daddy (1999)

“I had a mother lined up for him but she’s banging the Pepperidge farm guy and the kid won’t stop peeing or throwing up. He’s like a cocker spaniel.”


A personal favorite of mine is Sandler’s Big Daddy. While his roommate is away on business, a small child is delivered to Sonny’s apartment. It is, in fact, his roommate’s illegitimate son. In an effort to prove his responsibility to his girlfriend, and perhaps find some self worth, Sonny decides to keep the kid, but will soon discover that raising a child is no easy task. I seriously love this movie. It’s as heartfelt as it is funny, and Sandler’s performance is tender and adequately realized. 

6. Punch-Drunk Love (2002)

“I have to get more pudding for this trip to Hawaii. As I just said that out loud I realized it sounded a little strange, but it’s not.”


Punch-Drunk Love tells the story of a psychologically ill man who falls in love with a quiet and humble woman played by the ever-talented Emily Watson. He attempts to explore this romance while he battles off a phone sex line extortionist, buys large quantities of pudding to gain free airline miles, and deals with his irreverent and judgmental family. I believe this film is unquestionably the best on this list. While that is mostly due to director, Paul Thomas Anderson, Sandler is still utilized to his greatest capacity. This is his most sincere performance to date, and it is a humble and powerful entry to his resumé.

7. Mr. Deeds (2002)

“I promise to love you for fifty years more, even when your bosoms sag down to the floor.”


The final film in the Golden Years of Sandler and co., Mr. Deeds tells the story of a humble man named Longfellow Deeds from a small town, whose billionaire Uncle passes away and leaves Deeds his entire fortune. As Deeds travels to New York, he discovers what life in the big apple is really like as he falls in love with an undercover reporter played by the wonderful Winona Ryder. This film definitely walks the line between quality Sandler and the Sandler we’ve come to know today. It’s redemption is in its quotability and in its rich cast of unconventional characters. It is a very funny film which I believe you will, at the very least, giggle profusely throughout.

What do you think? Are there any other Adam Sandler films worth watching? Or are all of his films giant piles of dog crap? Let me know what you think in the comments section below! 

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