Adam Sandler’s Netflix movie Hubie Halloween sees the actor return to broad comedy and receiving middling reviews as a result, but when did the once-beloved actor’s films become so bad? Hubie Halloween may not be the worst received film of Adam Sandler’s career, but a milquetoast “it’s not terrible” is the best compliment that many critics are willing to give the horror-comedy.

The Netflix hit hasn’t earned a lot of critical love despite Hubie Halloween being different from Sandler’s other films, and that’s not a surprise for fans of the actor as, after the last decade and a half of duds, Sandler is almost known for making bad comedies now. However, a great many fans truly loved his earlier work, such as Happy Gilmore, Billy Madison, and The Waterboy, goofy comedy classics that even won the heart of some usually self-serious critics. So when exactly did Sandler’s shift from comedy icon to flop producer occur, and why?

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It’s a source of endless impassioned debate among fans of the actor whether his films were actually better back then or the films and their sense of humor remained the same as the world (and audience tastes) changed over time. Some claim that the target audience of his early “good” films simply grew out of his uniquely juvenile style of humor, but this explanation doesn’t account for how comedians like the late Robin Williams, Eddie Murphy, and Steve Martin altered their style along with their aging audiences (a few stray flops aside, particularly on the part of Murphy). But there’s a more concrete cause for Sandler’s gradual comedic decline. As Sandler’s singular focus on comedy waned so did his apparent interest in originality and innovation, leading the star to stop playing bizarre oddballs and start playing boring everyman protagonists and relying on the wacky premises of his later films to provide laughs (that never materialized).

Lucy and Henry in 50 First Dates

It may seem odd to call the likes of Happy Gilmore and The Waterboy “innovative” given how goofy the movies are, but casting Kathy Bates in the latter and the inspired ending of the former proves that Sandler was an interesting comic voice willing to take risks. Billy Madison is as anarchic and surreal as earlier comedy classics such as Ghostbusters and The Jerk but, much like their stars Bill Murray and Steve Martin, Sandler gradually moved toward more dramatic and mature roles. The problem was Sandler didn’t stop making immature comedies when he stopped finding them inspiring, and instead started relying on silly premises instead of interesting characters with his films becoming stale and predictable as a result. As Sandler's work has away from unadulterated silliness and incorporated more rom-com, action, and sci-fi elements, and these genre fusions haven't gelled well with his comedy. This results in duds like Just Go With It, Murder Mystery, and Pixels which are too goofy to work as genre films but whose protagonists aren't zany enough to be classic Sandlerverse heroes.

50 First Dates, for example, was one of Sandler’s first major critical misfires, and it’s one of the earliest films where the actor relies on a premise ("What if you had to win over your love interest anew every day?") instead of relying on a classic Sandler character. Despite this potentially interesting idea, the film is a thin and un-engaging rom-com that has none of the inventive charms of Sandler's earlier Barrymore collaboration The Wedding Singer. But where The Wedding Singer wasn't afraid to have Sandler play a weirdo with a heart of gold, his 50 First Dates character is a supposedly relatable straight man who mostly just feels forgettable. Since that first critical wobble, the actor has gotten lazier and more reliant on throwing in gross-out jokes for cheap laughs, a formula which hit its inevitable nadir in the genuinely offensive and tragically unfunny That’s My Boy. Sandler's return to playing an absurd figure in Hubie Halloween saw his reviews improve a little, but a decade and a half of relying on premises instead of his comedic characters for laughs blunted his once sharp comic instincts.

More: Theory: Adam Sandler Made Hubie Halloween To Punish Us For Uncut Gems