When Adam Sandler first broke out as a Saturday Night Live cast member, he probably wasn’t at the top of anyone’s list of future awards season contenders. But that’s life for you — full of surprises, like how the same guy who got into an on-screen fistfight with Bob Barker could prove to be a sharp, nuanced, and vulnerable dramatic actor.
Sandler has always kept his feet firmly planted in both worlds, as evidenced by his recently announced 2022 stand-up tour, and not all of his dramatic work has flourished — much like his comedy projects, which have sometimes been great and sometimes suffered from lazy execution or premises that were a little too far out there. (On the advice of counsel, at this time we will not be mentioning the existence of Jack & Jill or The Cobbler.)
But one consistency is this: When the Sandman really commits to a project, one that clearly has deep personal significance for him, the results can be truly extraordinary. That, and his occasional fearlessness when it comes to taking creative risks, has ensured his place as one of his generation’s greatest comedians — who might yet win an Oscar someday.
— Liz Shannon Miller
10. Sonny Koufax, Big Daddy
Following a breakup with his girlfriend, who thinks he’s too immature, Adam Sandler’s Sonny Koufax attempts to become a responsible adult by adopting and raising a five-year-old boy. Sonny Koufax is considered to be a major step in Adam Sandler’s acting career, deviating from Sandler’s usual crude humor to showcase him in a more heartfelt role. While Sandler could have chosen a completely serious role, Sonny Koufax had the perfect mix of innocent immaturity and heart that eased the audience into Sandler’s acting range. — Caitlyn Taylor
09. Stanley Sugerman, Hustle
A basketball savant in real life, Hustle feels like a passion piece for Sandler, as his immersion into the NBA realm is seamless. As prospect scout Stanley Sugerman, we see a determined Sandler attempting to not only make his dreams come true, but do the same for an unknown talent with immense potential.
Sandler plays well off of the unexpected performance from NBA forward Juan Hernangomez, as the two grow together both physically and as characters through their training sessions. Hustle serves as a reverse version of Rocky, where the emphasis is placed on this story’s Mickey Goldmill, and the lengths a trainer will go to prepare their protege for their end goal. – Joe Eckstein