Adam Sandler at 60: The Essential Films

On 9 September 2026, Adam Sandler reaches sixty. For most of that span, since his Saturday Night Live years in the early 1990s, he has been one of Hollywood's most durable and profitable entertainers, the kind of figure who can open a film on the strength of his name alone and who has built a career largely on his own terms. That durability matters. In an industry that chews through talent at speed, Sandler has remained consistently employed, consistently visible, and consistently willing to take chances, even when those chances landed him spectacularly on his face. By any measure of commercial success, he has succeeded wildly: his films have earned billions, his Netflix deal was transformative for him and for the company, and his comedic persona has proven remarkably elastic, stretching from dopey man-child to bereaved middle-aged father to desperate, furious gem thief.

What defines Sandler's work is precisely that elasticity. He is a comedian first, trained in stand-up and sketch, with an instinctive grasp of rhythm and the absurd, but he has never been content to stay in comedy. Where his early films lean on his gift for the ridiculous, his trajectory over three decades reveals a hunger to be taken seriously as a dramatic actor, and a willingness to collaborate with filmmakers (Paul Thomas Anderson, the Safdie brothers, Noah Baumbach) who see in him something worth exploring beneath the gags. His comedies tend to work as vehicles for his personality and his band of recurring collaborators: Rob Schneider, David Spade, Kevin James. His dramas tend to be about loneliness, regret, and the damage people do to themselves and those closest to them. The split between these modes is real, but Sandler moves between them with ease, suggesting they are not opposites but variations on the same thing: a talent for getting inside the skin of ordinary people, whether he is making them laugh or breaking your heart.

Macca has reviewed three Sandler films, and they offer a useful cross-section of his range. "Big Daddy" (1999) earns three stars, a fair assessment of a broad comedy that relies on Sandler's ability to play the well-meaning screwup, all noise and impulse, suddenly forced into the shape of a father. It is the kind of film that works because Sandler's naturalistic warmth survives the contrivance of the plot. "Mr. Deeds" (2002), which gets two and a half stars, is a gentler affair, built more on good humour than genuine laughs, with Sandler as the rube let loose in the city, a premise that lets him coast on charm and decency. Neither demands much of him. "Uncut Gems" (2019), however, receives four stars, and it is the film that changes the conversation entirely. Working with the Safdie brothers, Sandler is unshackled from likability, playing Adam Salstein, a jeweller in Flushing, Queens, consumed by gambling, infidelity, and a desperate hunger for the next score. He is frantic, duplicitous, hateful, and utterly alive, and the film demands everything of him: vulnerability, rage, intelligence, and a refusal to signal to the audience that he is a good man underneath. It is a performance that stands alongside anything he has done, and it suggests what Sandler is capable of when he gives himself over entirely to another vision of himself.

The films I've reviewed:

• Uncut Gems (2019) ★★★★
• Big Daddy (1999) ★★★
• Mr. Deeds (2002) ★★½

Sandler at sixty is still working, still finding roles and projects that interest him, still willing to make comedies for money and dramas for something else. That balance, that refusal to choose entirely, keeps him engaged in a way that suggests he will not calcify into legend or retreat into nostalgia. He remains fundamentally a working actor, which may be the most underrated form of success in cinema: the ability to keep working, to keep surprising, and to let other filmmakers see what you might become if you step out of your own light.

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