Written by Adam Sandler along with frequent screenwriting collaborator and fellow SNL alum Tim Herlihy, the Tamra Davis directed Billy Madison is turning twenty years old this year. The film still feels just as youthfully irreverent and gleefully chaotic as it did initially, even if Sandler’s manic appeal has waned of late, his innate ability to empathetically inhabit the affectations of a child having developed into an adult maturity stunted by the arrested development of his formative years on screen. While you’d be hard pressed to find any child of the 1990s for whom this particular comedy doesn’t hold at least some personal resonance, it’s impossible to watch what is one of Sandler’s greatest comic achievements and not come away feeling a little slighted by the weight of time and the weathering effects of age and maturity. Bottom line, Madison is a little dopier, sappier, and conceptually duller than remembered.

Whether it’s a case of viewers having simply outgrown the Peter Pan tights, or perhaps, more profoundly unsettling, we’ve realized that the Madison costume never fit Sandler’s decidedly burly frame as well as we had once imagined, Davis’ film is a dud from start to finish. However enlivened the picture may be by the charismatic appeal of Sandler in his prime, his continuing dramatic defiance towards larger creative growth has trapped him in the guise of this his greatest character. Forever pining after beautiful women with whom he holds nothing in common, content to suckle at their ample cleavage and remain the preeminent man-child.

Nevertheless, Sandler’s appeal does not appear to be going anywhere anytime soon. His continuing box office successes astound under the corporatized umbrella that is Happy Madison Productions, allowing Sandler to weather even the harshest storms of critical derision while remaining free of self-conscious appraisal. The emotional stagnancy of some of his more recent creative excretions have had no effect on his vitality as a bankable Hollywood star. And yet, despite all of his immature excess, Sandler is still an undoubtedly viable dramatic performer. On multiple occasions, independent talents have written roles for him backed by challenging scripts and nuanced adult themes, wherein he has shown an amazing aptitude to adapt, despite being more personally drawn to the familiarity of playing the intellectually vapid.

In films such as Paul Thomas Anderson’s Punch-Drunk Love, Sandler is able to play off of his more characteristically comic inability to engage emotionally with the object of his affection. Under the focused gaze and conceptual impetus of Anderson’s direction and writing, Sandler’s lack of intimacy ends in chaos and acts of unfocused violence, exposing his comic persona to the fragility of a world unclouded by the immaturity of nostalgic longing. Similarly, in Judd Apatow’s Funny People, Sandler is forced to grapple with the ephemeral nature of the studio comedy, resulting in a cosmic collapse of the self, an existentialist take on the creative desolation of the star of Big Daddy. Even in dramatic roles that don’t quite work thematically, (see James L. Brooks’ Spanglish or Mike Binder’s Reign Over Me), Sandler’s sense of disorientation in an adult world is sympathetically achieved. His sense of dissatisfaction with maturity echoes our own, even if we don’t want to admit it, let alone confront such a fundamentally regressive trait in our own personal character.

But, if last year’s Blended serves as any indication, Sandler is still not ready for prime time. His own creative inclinations are persistently sophomoric at best (see Grown Ups), and comically stagnant at worst (see Jack and Jill). Instead of outgrowing the Billy Madison costume, Sandler has refused to take it off. Occasionally, he’ll try on more formal wear when called upon to take a role in someone else’s more ambitious project (see last year’s Men, Women & Children or The Cobbler), only to don those old blue jeans and baseball cap once more to lesser and lesser fanfare, albeit to a comparatively consistent flow of monetary returns.

Looking back on it now, Billy Madison may only be a slightingly provocative farce, but its humor is empathetically felt. In his first box office success in the lead role, Sandler is unwilling to make fun of a character that might be more broadly ridiculed in the hands of such successors as Will Ferrell and Adam McKay, which is its greatest triumph, however often to a fault. Perhaps the most telling moment of Billy Madison comes when Billy returns to a grade school classroom filled with literal toddlers, his true intellectual peers, with whom he holds more in common than his classmates in high school, his actual personal rivals. At the end of this scene, Sandler is left literally shaking the baby fattened cheeks of his own fading innocence, pleading the case to never grow up with an earnestness that has proven to be not entirely disingenuous, funny only in how tragically prescient such a skit has become in hindsight, twenty years down the road.