Top 10: Best Adam Sandler Performances (Yes, Really)

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Adam Sandler isn’t the actor who normally receives acting retrospectives. As the illustrious recipient of nine Razzie wins, it’s fair to say his quality meter can be quite off. Yet, as a preteen of the 2000s, Sandler holds a place in my heart (which has thankfully grown up, along with some of my tastes). His frat-boy humor can (and often does) throw tact and good taste out of the window. However, his best work shows the sadness of a life as shallow as the one his movies tend to glorify.

Sandler isn’t enjoying the same automatic box office success that greeted him for over a decade from “The Waterboy” through “Just Go With It.” However, he’s still in movies, despite being Netflix’s go-to schlock guy. Sandler headlines the animated film “Hotel Transylvania 3: Summer Vacation,” opening Friday. As the voice of Dracula, Sandler has reached his first ever trilogy. At least until we’re subjected to “Grown Ups 3” on Netflix.

As we enter the phase of children’s movie voiceovers for Sandler, let’s take a look back at his best performances over the past two decades. Yes, there are enough to fill out this list.

  1. “Bedtime Stories” (2008)

What if the bedtime stories you tell kids come to life? Sandler anchors Disney’s family comedy with a lightness of touch that he’s rarely known for.  Yes, the film is incredibly simple. However, Sandler makes the most of the high concept family outing. Now that he’s making his living on the “Hotel Transylvania” franchise, it’s interesting to see how strong and likable he was on his previous family outing.

  1. “Billy Madison” (1995)

The obnoxious man-child begins and takes literal form with Sandler’s first leading role. “Billy Madison” finds Sandler as a rich adult who’s never finished school. In order to win back his inheritance, he must go from Kindergarten through high school and prove he’s capable of learning. Very little of this premise is endearing on paper, especially in today’s climate. However, there’s enough heart behind Sandler’s boisterous character to elicit guilty laughter. Sure he screams at children. However, he also pretends to wet his pants in order to make a bullied classmate feel less lonely. There may not be a lot of depth to Billy. Yet, there’s still quite a bit of heart.

  1. “Big Daddy” (1999)

“Big Daddy” resembles Adam Sandler’s book report version of “Kramer vs Kramer.” An oafish man winds up saddled with a kid (Cole & Dylan Sprouse) he never knew existed. The two bond, with Sandler’s Sonny giving the kid free reign to do whatever he wants. Yes, this includes changing his name to Spiderman. Eventually, fate (and child services) intervene and Sonny may no longer be the guardian of Spiderman. It’s a tale as simple and old as time. Yet, Sandler and the Sprouse kids have a genuinely fun chemistry that’s hard to resist.

  1. “Click” (2006)

No, Academy Award nominee “Click” is not a great film. It struggles to even be good at points. Still, there is something weirdly ambitious about this entry. Sandler plays Michael, a man who shops in the Way Beyond section of Bed Bath and Beyond to obtain a remote control for life. This allows him to fast forward through the parts of life he doesn’t like. Seems fun enough, right? Wrong. Many were thrown by the film’s tonal shifts. As Michael moves forward through time, he realizes how much of his life he misses. The mundane moments he wants to miss become the moments he wishes he could’ve lived. The film barrels towards a dark conclusion before letting up in typical light comic fashion. Still, credit should be given for a Sandler vehicle pulling the rug out from under its audience expecting just fart jokes.

  1. “Spanglish” (2004)

James L. Brooks’ 2004 flop possesses some strange, tangible insights into the cultural and economic divide between a Beverly Hills family and their housekeeper. Flor (Paz Vega) flees Mexico, with her daughter in tow, to Los Angeles. She soon becomes the housekeeper for the Clasky family. Tea Leoni gives a brilliantly over-the-top performance as Debra, the exhausting housewife that is less of a caricature than you would want to believe. Adam Sandler turns in his most humble and romantic performance as her husband John, a chef struggling with success and what that means for him. He conveys an affable “good guy” vibe that weirdly contradicts his SNL style characters beforehand. Yet, he sells it well, while showing there’s a screwed up guy beneath it. It’s a movie that aspires to a lot of things. Perhaps that’s why Sandler keeping it simple works beautifully.

  1. “The Wedding Singer” (1998)

No one brings out the best in Adam Sandler quite like Drew Barrymore. In their three collaborations together, Barrymore proves to be a wonderfully light tonic to Sandler’s more boorish antics. In their first film, Sandler plays Robbie Hart, a wedding singer engaged to the wrong girl. He meets Julia (Barrymore), a waitress who similarly has found herself on the road to marrying the wrong guy. Meet cute ensues as the pair walk earnestly through every romcom trope. Still, one can’t deny that sparks fly when Sandler and Barrymore are on screen together.

  1. “Happy Gilmore” (1996)

Sandler’s “Happy Gilmore” represents one of the few times where going over the top works. His follow up to “Billy Madison,” Sandler ends up going louder with his next comic incarnation. Happy Gilmore is a hockey player with anger problems who finds partial success in the golf world thanks to his incredible drives. The film works because the logline premise is inherently funnier. Pairing Sandler’s larger than life comedy with the stuffy golf pro tour proves to be a winning fish-out-of-water idea. This is best articulated when Happy is paired with “Price is Right” Bob Barker in a celebrity tournament. Like Happy, Sandler swings for the fences. Luckily, the movie is doing so right alongside him.

  1. “The Meyerowitz Stories (New and Selected)” (2017)

In a Noah Baumbach directed cast featuring Dustin Hoffman, Ben Stiller and Emma Thompson, Adam Sandler shockingly emerges best in show. His Danny begins the movie trying in vain to park the car in front of his daughter. From there, we learn more about how Danny is perceived around his family. He’s the one who stuck around, partially because everyone assumed he had nothing better to do. He never had the artistic skill and ambitions of his other siblings. It turns out his familial devotion may be his downfall. The people he cares for show him very little of the same affection. Sandler understands lovable losers and makes Danny the most rootable soul of the film.

  1. “50 First Dates” (2004)

The masterpiece of Adam Sandler’s frat-boy filmography remains “50 First Dates.” Yes, it’s not without some trademark cringeworthy lines for the teens. However, the film sidesteps its potentially creepy premise much better than one would expect. Adam Sandler’s Henry falls for Lucy (Drew Barrymore), a woman with a condition that causes her to lose memory each day. The film shows an aging lothario confronting a kind of commitment he’s been running from all his life. Every day, he chooses to win over the love of his life because he profoundly loves her. This involves going through the days where she’ll fall for him, the days she’ll hate him and the days she just copes with her trauma. Sandler sells his chemistry with Barrymore, the best co-star of his career. He knows the emotional stakes of the romance and plays to it accordingly.

  1. “Punch Drunk Love” (2002)

Paul Thomas Anderson knows how to grab dynamic performances from the most unlikely of places. Opening the same year as “Mr. Deeds” and “Eight Crazy Nights,” few expected a dramatic turn out of Adam Sandler. Of all people, the fart king is working with the “Boogie Nights” and “Magnolia” director.

At first pass, Sandler’s performance is a strange and quixotic thing that appears as rough and grotesque as some of his bawdier manchildren. Barry Egan wraps himself in his own neuroses. He finds more time to scam a bulk yogurt deal than spend any time with his many sisters, whoring with a Greek chorus of antagonizing digs. However, he develops a relationship with Emily Watson’s Lena that seems too good to be true. This is mainly because Barry shows little skill or resources to handle a relationship with anyone other than himself. Add on a threatening phone-sex line handler, played by Philip Seymour Hoffman, to further complicate the situation. Sandler works hand in hand with Anderson to put us in the headspace of Barry’s anxiety. It’s an exhausting and grueling experience and one that comes together thanks to Sandler’s dedication.

What’s your favorite Adam Sandler performance? Share your guilty pleasures in the comments below.