Check Out Adam Sandler’s Best Comedy Before It Leaves Netflix — and Ahead of ‘Jay Kelly’

Adam Sandler is receiving Oscar buzz for his performance in Noah Baumbach‘s showbiz drama Jay Kelly. This is a sentence that would cause critics from the 1990s and 2000s, who viciously railed against Sandler’s juvenile, lowbrow style of comedy in Happy Gilmore, Little Nicky, and Jack and Jill, to get in touch with reality. The tides have changed—evident by the relatively warm reception given to Happy Gilmore 2. However, Sandler deserves his flowers, as he has proven to be a gifted dramatic actor in prestige films by auteur filmmakers like Punch-Drunk Love, The Meyerowitz Stories, and Uncut Gems. Still, time has been Sandler’s greatest ally, as people look back on his once-derided star vehicles with fondness today, in an era where studio comedies seem permanently stagnant. Before starring opposite George Clooney in Jay Kelly, 30 years ago, he crystallized his unique screen persona in arguably his signature movie, Billy Madison, which is leaving Netflix at the end of the month. Sandler’s performance is grating, obnoxious, and completely ludicrous, but that’s why it’s brilliant.

‘Billy Madison’ Cemented Adam Sandler’s Star Persona

If an actor made an impact as a cast member on Saturday Night Live, chances were they would be gifted a studio comedy either directly based on a character on the NBC sketch show or a star vehicle that complements their comedic attributes. Although Adam Sandler was unceremoniously fired from SNL, his skill set was simply too bizarre and unmistakable to leave on the table. In 1995, the year of his firing, Sandler was given studio money to play the titular Billy Madison, a character with the tactless edge and manic rage of an SNL character who embarks on a hero’s journey. Audiences were immediately won over, and he became one of America’s top movie stars and cultural icons for the next three decades.

Directed by Tamra Davis and co-written by Sandler and his go-to collaborator, Tim Herlihy, Billy Madison follows the lazy and spoiled heir to a hotel magnate who enrolls in a fast-tracked K-12 school program to prove that he’s worthy of his inheritance, all while being undermined by the business’ determined successor, Eric Gordon (Bradley Whitford). Critically reviled upon release, the film has endured in the public eye, and the role cemented Sandler’s firebrand on-screen energy that you either love or hate. Even for the most cynical viewers, Billy Madison frequently offers resigned chuckles, and its self-awareness of its own stupidity makes it easier to laugh along with the character’s array of goofy voices and fits of rage.

In the 30 years since its release, Billy Madison acts as more of a relic of a bygone era, as Sandler, now 59, has comfortably transitioned to perfecting the chill dad archetype in Happy Madison productions. Prominently displayed in Happy Gilmore 2, Sandler is a passive figure in his movies, stepping aside and letting his friends bring the flavor to the screen. In Billy Madison, however, the film rests on Sandler’s shoulders, who is an unstoppable force of gonzo comedic bits that blur the line between childish slop and artistic brilliance. Speaking to his lack of egoism, Sandler fearlessly paints himself as an unlikable borderline sociopath, which only gravitates us to love him as an uncanny oddball.

The Uncanny Artistic Brilliance of ‘Billy Madison’

From what we know about him now, bits like the talking shampoo and conditioner bottles and rant over the “puppy who lost his way” story feel like less of a product of an immature man-child and more of a radical creative powerhouse breaking all the rules and expected sensibilities of a leading man. His gleeful approach to crafting something of such chaotic messiness and unbridled rage made him the Jerry Lewis of his era, another comedic star who was only appreciated in retrospect.

Billy Madison cemented all the Happy Madison hallmarks, everything from the product placement and the love interest in Veronica Vaughn (Bridgette Wilson-Sampras), who’s way out of his league. While Sandler is the star, he lets his friends, like SNL writer and recent One Battle After Another bit player Jim Downey, Steve Buscemi, Norm Macdonald, and Chris Farley (you can visibly see Sandler trying not to burst into laughter while talking to Farley as the depraved bus driver), who each deliver unforgettable lines in just a few scenes. The heavily improvised, if not formally sloppy, nature of Billy Madison feels like the work of a comedy revolution that paved the way for movements ushered out by Adam McKay and Judd Apatow.

If Adam Sandler kept playing obnoxiously broad archetypes like Billy Madison forever, his act would have worn thin, but he found ways to evolve and expand his comedic repertoire as a romantic lead in The Wedding Singer, action star in You Don’t Mess With the Zohan, and self-reflective meta character in Funny People. Sandler’s demonstration of hostility and vibrant rebellion surely attracted him to directors like Paul Thomas Anderson, Noah Baumbach, and Josh and Benny Safdie and motivated them to unlock his true genius as a dramatic actor.

Billy Madison is available to stream on Netflix in the U.S.