Fun
Frisky
Nostalgic
Intense
Adventurous
Choked Up
Curious
Romantic
Weird
There’s an entire generation of teens who only know Adam Sandler from recent films like The Do-Over and The Ridiculous 6, which is, in a word, bananas.
From the early ’90s to the mid aughts, Adam Sandler was one of the most influential names in comedy. He portrayed iconic characters like Canteen Boy and Opera Man on Saturday Night Live; penned classic tunes like “The Thanksgiving Song,” “Lunch Lady Land,” and “The Chanukah Song;” and produced a number of well-received comedy albums.
After five years on SNL, Sandler made the lucrative transition to film, starring in cult favorites like Billy Madison and Happy Gilmore before moving on to more emotional comedies like The Wedding Singer and Big Daddy. I cannot stress how popular Adam Sandler was during this stretch of time. Before people were dropping “Milk was a bad choice” and “I’m kind of a big deal” in everyday conversations, they were saying things like “Chlorophyll? More like BOREophyll,” and “The price is wrong, bitch.” The Sandman was the talk of the lunch table.
Over the last ten years, Sandler has transitioned into a different phase of his career. Some may like his new stuff, but I’m a fan of Sandler-classic. If your Sandman scale also skews more towards The Waterboy than Grown Ups, you’ll enjoy this list of the five best Adam Sandler movies available to stream.
'The Wedding Singer '
The Wedding Singer is the first of many on-screen romances between Sandler and Drew Barrymore, and the pair’s adorable chemistry is on full display in this highly-rewatchable 1998 gem.
While better known for silly antics and broad comedy, Sandler proves he possesses the requisite theatrical chops to portray a convincing leading man as he plays Robbie Hart, a wedding singer attempting to get over a recent breakup. Sandler toggles between hilariously deranged (like when he’s singing “Love Stinks”) to surprisingly swoon-worthy in this enduring ’90s classic.
'Big Daddy'
In a seven-year span, Sandler released Billy Madison, Happy Gilmore, The Wedding Singer, The Waterboy, and Big Daddy. That’s an impressive array of comedies.
While this 1999 film— in which Sandler becomes an unlikely father after adopting a child to impress a girl — isn’t the laugh out loud funniest of the group, it’s the most emotional as Sandler unleashes a surprising amount of depth as he portrays a man-child thrust into adulthood.
“We wasted the good surprise on you!”
'Punch-Drunk Love'
Paul Thomas Anderson’s Punch-Drunk Love is a wholly unique delight.
Sandler gives a revelatory performance as Barry Egan, a troubled novelty supplier who’s attempting to conceal an inferno of emotion. As someone who grew up idolizing Sandler’s comedy, watching this visually and emotionally mesmerizing film can be frustrating because you see the type of performance the actor is capable of delivering (when he’s provided with the opportunity) as a leading man.
'Mr. Deeds'
Looking to rebound from the debacle known as Little Nicky, Sandler ‘s next film was Mr. Deeds, a comedy about an affable small-town guy who inherits a massive fortune.
Honestly, I didn’t love Mr. Deeds when it first premiered, but countless years of catching bits and pieces of this fish out of water comedy on TV have led me to appreciate the film’s quirky charms. There’s “good Adam Sandler” and “bad Adam Sandler,” and I contend that Mr. Deeds falls into the lower tier of the former rather than the latter.
'Spanglish'
Written and directed by the legendary James L. Brooks, Sandler leads an all-star cast in the 2004 dramedy Spanglish.
Sandler once again proves he’s more than capable of adapting to a role that requires some theatrical nuance, but it’s a team effort in Spanglish as Tea Leoni and Paz Vega also deliver wonderful performances in this heartfelt comedy.
