5. Funny People (2009)
Funny People lied to us.
Judd Apatow’s film was promoted as if a light-hearted romp about comedians learning to write funny sketches and stand-up routines together, the cast of Apatow regulars like Seth Rogen and Leslie Mann supporting Adam Sandler in an almost self-referential role of a comedian looking to get back to his best.
What Funny People ended up being was a comically touched drama about overcoming serious grief in the midst of bitterness, with Sandler offering a performance radiating underlying anger and resentment that at times made him scary.
Sure, this film has some solid funny moments, but Sandler’s performance is one of an entirely miserable man who has lost the only things that mean anything to him, yet has done so without ever stopping to realise.
If there was a point in this list where you might want to down your anti-Adam tools and embrace Sandler as a capable dramatic force, that’ll be now.
4. Reign Over Me (2007)
2007 movie Reign Over Me saw Adam Sandler undergo a transformation of sorts.
Sandler, who had already starred in a number of dramas, removed all of his comedic sensibilities in an attempt to tackle this role head on, and tackle it he did.
The performance The Sandman put together for this piece about two old friends reconnecting in the aftermath of 9/11 was one of sheer grief and instability, his performance of the movie’s anchoring monologue being nothing short of spectacular.
The movie itself had its issues but remains one of the actor’s very best, his performance here playing with the idea of Sandler as a performer of adult naivety and subverting it by attaching deeply tragic history to him, something Sandler carried with a maturity and deftness that remains memorable to this day.
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3. Punch-Drunk Love (2002)
Adam Sandler blew his comedy history out of the water in his 2002 universally praised performance in Paul Thomas Anderson’s Punch-Drunk Love.
Having achieved almost unparalleled heights as a comedic talent in the 90s, Sandler subtly worked his way into the dramatic sphere with brief moments in the likes of Big Daddy before diving head first into this anchoring role; the first real glimpse of something deeper and more meaningful from the powerhouse talent.
It was a performance so shocking in its sophistication and so utterly fantastic in its own right that many still consider this to be the performance of 2002, and one that should have been nominated for an Oscar.
P.T. Anderson tapped into Sandler’s innocent portrayals to offer something deeper and potentially more sinister as a side note to Sandler’s usual performances, while Sandler himself was willing to go the extra mile to truly embrace the testing role at the centre of the director’s borderline art-house piece. It was a match made in heaven.