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Best Adam Sandler movies

Writer: Casey Lee


Can Adam Sandler's "The Cobbler" fare better than his best comedy movies?

While Adam Sandler may not have been hitting the home runs with his recent outings "Blended", "That's My Boy" and "Jack and Jill", things may finally be taking a turn for the better for Sandler to be funnier as ever with upcoming movies like "Pixel". But before that, let's start with "The Cobbler", a potentially heart-warming dramedy about a cobbler who can literally live in the shoes of others.

This could be one of the more dramatic roles that we have seen Sandler taken on in a while. What's that? Adam Sandler had taken on dramatic roles before? Why of course! So in anticipation to see if Sandler can finally bounce back to win our laughs, hearts and maybe a few tears in "The Cobbler". Here's our list of Sandler's best movies that reminds us how great a performer that Sandler once was and can be again.

Billy Madison

Billy Madison is a free-loading heir to his father's Fortune 500 company, but in order to prove his worth to inherit the corporation, Billy must first complete his education. Fresh off from his stint at SNL, Adam Sandler made his name known in Hollywood with this rumbustious breakout that would be the brand of Sandler's comedies. Aside from the straight-faced jokes from the lines by Sandler and Tim Herlihy, the mild racial stereotypes, and most of all the vulgar slapstick that is steeped in parody (Thanks for hitting me, Veronica!), it was in "Billy Madison" that Sandler proved himself to be the next torchbearer of comedy after Jim Carrey himself. This and its follow-up "Happy Gilmore" would be the loving calling card for Sandler to form his own studio, Happy Madison.

The Wedding Singer

While Sandler had starred beside a fair share of attractive female leads from Leslie Mann, Bridgette Wilson, Patricia Arquette to Jennifer Aniston, none have come close to having that chemistry Sandler had with Drew Barrymore. So it is only fitting that their first collaboration together in "The Wedding Singer" should come into this list, with Sandler showing one of his sweetest side from a hopeless wedding singer to the hopeless romantic who wants to grow old with you. It is no accident that the Sandler and Barrymore combo would make two more outings together (most recently "Blended"), and we would be at a remiss if "50 First Dates" didn't come close to being on this list instead.

The Waterboy

As a sheltered boy with special needs, Bobby Boucher Jr. works as the waterboy for the local high school football team until he gets fired. When his inner rage is tapped to turn him into a fearsome tackler on the field, the once looked down upon kid is now the school hero. Looking at the later movies of Sandler from "Little Nicky", "The Longest Yard" and "Anger Management" that followed after it, it becomes quite apparent that the sum is much larger than its parts. That sum is "The Waterboy". Stealing from his own silly and slurring antics of "Billy Madison" and stretching on the political incorrectness with the righteous ignorance being the premise of Bobby's little world, Sandler still manages to create a lovable character that fits right into the tropes of an underdog sports movie that would let every waterboy have their day in the sun.

Big Daddy

When a five year old boy ends up on his doorstep, toll both operator and perpetual slacker Sonny Koufax thinks that by adopting the child, he is able to show the responsibility that his estranged girlfriend needs in order to win her back. As he juggles the duties of being a parent, Sonny finds his own issues with his own father and what he expects of him. Sandler's characters before this have always depended on us rooting for him, so that we can laugh with him through his misadventures. In "Big Daddy" though, Sandler is barely even trying to win our affections, if not appearing detestable altogether, for being the irresponsible father that he is. However, Sandler still manages to make Sonny work till we can't hate him, despite the overwhelming evidence that is thrown against him. "Big Daddy" may have cemented Sander's appeal, being his highest grossing movie that is worth over USD$163 million that would set his eternal partnership with Sony in stone.

Punch Drunk Love

Socially inept novelty toilet plunger salesman, Barry Egan, is trying to find a human connection. After an accidental meeting with a friend of one of his overbearing sisters, Barry breaks out of his shell to go after her, even with a gang of blackmailers are after him.

Although Sandler has shown more of his acting chops in heavier toned features with more serious directors like Judd Apatow ("Funny People"), Mike Binder ("Reign Over Me"), and James L. Brooks ("Spanglish"), it is the two names that no one could possibly imagine being said in the same sentence; Adam Sandler and Paul Thomas Anderson, that would turn out to be one of the weirdest but most game-changing collaboration ever for both parties. Sandler in "Punch Drunk Love" is arguably the best time we can really see Sandler as an actor. Under Anderson's direction, Sandler is transformed from crass comedian into a muted and nuanced character, and his whacky side is used to fuel a dangerous and violent energy that is the power of love.

Despite being one of the few outings that did not enjoy the obscene box office takings that Sandler and Happy Madison are accustomed to, it was the nearest that Sandler was within range of critical acclaim with his only Golden Globe nomination to date.

Cinema Online, 08 April 2015

Related Movies:
Pixels (13 Aug 2015)
The Cobbler (09 Apr 2015)


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