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Adam Sandler - Punch-Drunk Love

With Uncut Gems, Adam Sandler is once again on top. It'd be an understatement to suggest the comedic actor hasn't always received critical or even commercial admiration, but his acclaimed turn in the newest A24 film is considered one of the Saturday Night Live veteran's best to date. There's even a chance that The Sandman might earn his first Oscar nomination for his latest performance. If that's the case, then surely it'll be a major turning point for Sandler's always winding career. For all the hit movies he's had throughout his 20-plus years in the moviemaking business, there have been a fair amount of flops along the way, to put it lightly

Either critically, commercially or both, Adam Sandler has had his highs and his many lows. For every stunning dramatic turn that he pulls, like the one he provides in Uncut Gems, there are several misfires that almost make you forget how good or funny he was in his greatest triumphs. So we're now taking this opportunity to look back on Sandler's vast and varied career and explore the great, the good and the very not-so-good movies found therein.

Adam Sandler's Best Movies

Whether it's comedies or dramas, Adam Sandler has often excelled on the silver screen. While his misfires might make people forget how good he can be, these films in particular make an easy case for why he's both one of the biggest comedy stars in the world and a potential Oscar nominee this fall.

Adam Sandler - Punch-Drunk Love

Punch-Drunk Love (2002)

Though not without its detractors, Punch-Drunk Love was a major turning point in Adam Sandler's career. Having defined himself as a goofy, boyish comedian through his quirky cast of characters on Saturday Night Live, and his run of commercially successful studio comedies throughout the '90s, Paul Thomas Anderson's masterpiece is a stunning revelation for Sandler. It showed the stunning complexity and undervalued conviction of his character work with Barry Egan, a socially awkward, psychologically troubled, emotionally-stunted businessman who finds himself in a hornet's nest of trouble over the course of the film's intense 95-minute runtime.

The depths of the underlying sorrow, burning rage and frustration, and internal, festering self-loathing provide the fuel for his fires that burn his soul when he finally finds his soulmate in Emily Watson's Lena Leonard. It's a deeply unconventional love story, one that confused and dismayed Adam Sandler's core fanbase when it was released. Nevertheless, this is his finest work to date.

Adam Sandler - Billy Madison

Billy Madison (1995)

After establishing himself as a fan favorite on Saturday Night Live, Billy Madison was the movie that proved that the TV actor had what it took to be a major movie star. Though savagely torn apart by critics at the time, the studio comedy was nevertheless an immensely profitable commercial favorite, providing one of the goofiest and most inspired film premises of Adam Sandler's career when the title main child must repeat grades 1-12 in order to inherent his father's fortune.

The immensely silly and wacky comedy was the one that helped mold the public's image of the actor, especially one that was gleefully lazy, willfully immature and prone to fits of shouting. While those factors were detrimental to Sandler's likability in his weaker movie efforts, it worked hilariously in Billy Madison. Filled with energy, insanity, and spunk, this mid-'90s charmer is still one of Sandler's funniest, most quotable films.

Seth Rogen, Adam Sandler - Funny People

Funny People (2009)

After establishing himself as a dramatic/dark comedy heavyweight with his phenomenal performance in Punch-Drunk Love, Adam Sandler opted not to pursue more intensive characters and artistically challenging endeavors, veering closer towards the studio comedies that made him a matinee superstar. Minus the rare Spanglish or Reign Over Me, Sandler's acting choices were comfortably conventional, opting not to push too deep into anything too soulful or artistically diverting. But Sandler surprised everyone by providing yet another compelling, layered performance, and in a studio dramedy no less!

Judd Apatow's Funny People is an extensive, sometimes belabored industry tale that focuses on a struggling comic who is faced with a life-threatening diagnosis and finds himself reflecting on his past mistakes, including several cinematic flops. Whether it's intentionally soul-searching or only appearing that way, Adam Sandler gives another stunning performance in this tender, contemplative, and yes, very funny film.

Adam Sandler - Happy Gilmore

Happy Gilmore (1996)

If Billy Madison showcased Adam Sandler's potential as a film star, Happy Gilmore cemented the performer as one of the biggest names in comedy in the mid-to-late '90s. The kooky story of a rage-friendly rejected hockey player who finds an unlikely calling in competitive professional golf, Sandler's signature flair for screaming, shouting and over-the-top displays of fragile male frustration came to possibly peak form in this film.

It showed the comedic actor losing his mind on the golf course and even participating in a brawl with the one-and-only Bob Barker. Arguably even more absurd than Billy Madison, these two films complimented each other well. They both provided the comedy foundation through which Adam Sandler propelled his career.

Adam Sandler - The Meyerowitz Stories (New and Collected)

The Meyerowitz Stories (New And Collected)

With Uncut Gems, Adam Sandler is in the awards conversation for his visceral, unnerving performance. But only a couple years earlier, the movie star delivered another tour-de-force performance that would've gotten Sandler into the awards consideration had the movie gotten its proper due. That film was The Meyorowitz Stories (New and Collected) from writer/director Noah Baumbach, who is also looking to enter awards consideration this year for his newest film, the similarly excellent Marriage Story.

Featuring a starry ensemble that includes Ben Stiller and Dustin Hoffman, Adam Sandler's dynamic and emotional, yet often understated performance proved a captivating new look at the actor, one who was willing to provide a performance that was both richly funny but heartbreakingly human. Showcasing even more vulnerability and humility than even his other great performances, it's clear that this performance in particular allowed Sandler to expand his dramatic horizons, which likely paved the way for his extraordinary new turn in Uncut Gems.

Adam Sandler's Worst Movies

Alas, for all the good work he's done throughout the years, Adam Sandler has often depleted his goodwill through an unfortunate stream of mediocre or outright terrible movies. It hasn't always been pretty. When Sandler makes a stinker, it can result in some of the worst comedies in recent memory.

David Spade, Adam Sandler, Chris Rock, Kevin James - Grown Ups 2

Grown Ups 2 (2013)

In every one of Adam Sandler's best movies, you can see the clear skill and effort that are on-display. Oftentimes when he's pushed to give a strong, soulful performance, Sandler will deliver, even when the movie itself doesn't always give the goods. (I'm looking at you, The Cobbler and Men, Women & Children.) Nevertheless, when Sandler is absolutely slumming it, it's even more apparent — and it's certainly much more disappointing.

As a result, a weak sauce comedy like Grown Ups 2 is utterly devoid of wit, heart or winning humor. The jokes are tired, derogatory and lame — and that's when the ensemble comedy even decides to have jokes. Most of the time, this hangout movie with Adam Sandler, Chris Rock, David Spade, Kevin James and several other underutilized actors is the worst type of Happy Madison effort. It is offensively dumb, soullessly shallow and wholly half-hearted.

Adam Sandler - Jack and Jill

Jack And Jill (2011)

If you ever wanted to know what it is like to have nearly $80 million dollars and throw it all into a dumpster fire, look no further than Jack and Jill. The foul, soulless 2011 studio flick is like a bad Saturday Night Live parody-turned-real-life Sony disaster,;the type of movie that anyone involved should be embarrassed to be associated with. The creatively-dead comedy finds Adam Sandler playing a pair of twins, the straight-laced Jack and the deranged Jill, as these two dysfunctional twins find themselves reconnecting over a series of wacky encounters.

It is a witless, draining effort, one that seemed beneath even the low standards of Adam Sandler at this time. You know it's bad when even a strangely dedicated Al Pacino cannot save your bankrupt project. It's no wonder Jack and Jill became the first (and only) film in Razzie history to win every single award in one year. That is an astonishing feat, but it's well-earned here.

Adam Sandler - That's My Boy

That's My Boy (2012)

An aggressive, mean-spirited attempt to transition Adam Sandler's comedy into the R-rated comedy territory that dominated the studio genre at the time, That's My Boy is an entirely unpleasant ordeal. Filled with unlikable characters, unbecoming jokes and just an all-around nastiness in terms of its focus and tone, this ill-conceived project finds Sandler playing Donny, a single parent who fathered a child with his teacher when he was a teenager. It is very apparent to see why this comedy doesn't work. In fact, it's crazy it was made in the first place.

Nevertheless, this uncomfortable, unfulfilling movie is a filthy, off-putting effort all-around, never allowing itself to earn its eventual left-heel attempts at poorly-rationalized emotional resonance. The actor has pushed himself to make more R-rated movies recently, and while there are many better than That's My Boy, it's hard to think of many worse.

Adam Sandler - The Do-Over

The Do-Over (2016)

Outside of his incredible dramatic turns in the past few years, Adam Sandler hasn't necessarily been producing his best work. For every Meyorwitz Stories or Uncut Gems, there are several dead-in-the-water Netflix movies that aren't even bothered with making themselves look presentable.

While there are many bad movies from this streaming service deal to pick from, including the horrendously panned The Ridiculous Six and the intolerable Sandy Wexler, The Do-Over might be the worst of the bunch — which is saying something. Starring alongside David Spade, The Do-Over is another foul-mouthed, gross-out friendly adventure story that doesn't have the humor or heart to be entertaining. If only we could have gotten a do-over here...

These are only a handful of the classics (and not-so-classic) movies made by Adam Sandler. Surely, there are several others to pick from with this line-up. In particular, the worst section could easily pack at least a few other titles to add to their growing collection, like perhaps Little Nicky. Please pick your favorite Adam Sandler movie in the comments, and let us know your favorite and least favorite films from the famous funnyman below. Also, be sure to check out Uncut Gems whenever it hits theaters starting December 13.

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