In SNL IN REVIEW, we look back at some of the notable cinematic efforts from Saturday Night Live alum, and place them in context of the actor-comedian’s career.

During his 2014 media blitz for Inherent Vice, director Paul Thomas Anderson spoke affectionately on “The Denise Show,” an early ’90s SNL skit featuring Adam Sandler. The sketch is classic Sandler– featuring the performer as a damaged TV host, recovering from the pain of a recent breakup.

One minute, Sandler is harmless, charming even… the next he’s “screaming, and his eyes go black,” in the words of Anderson.

The last “Denise Show” aired in March ’94, weeks before shooting began on what was Sandler’s first starring role. The film was Billy Madison, a raw, silly, punk rock thesis statement which drew on Sandler’s quasi sociopathic persona. He’d honed his anti-comedy with oddball skits like “The Denise Show,” and undoubtedly co-wrote Billy Madison in a bid to translate that sensibility to film.

Billy Madison, which turns 20 this week, became the basis for a long, profitable career for Sandler, who remains one of Hollywood’s box office draws (more or less). Arguably, he perfected the Sandler role best in 1996’s Happy Gilmore. But it’s in Billy Madison that you see him assembling all the pieces for his onscreen empire.

Today, films produced by Sandler have grossed over $2.5 billion at the box office. But how could an inconsequential film like Billy Madison, about a spoiled man-child going back to grade school, result in one of Hollywood’s few non-Marvel Comic franchises? The answer is in the way Sandler evokes the weird, cartoon logic of comics, building on the tropes first begun in Billy Madison.

As a character, Billy is Proto Sandler: laidback but prone to sudden fits of anger. In later films, the character would be presented as a guy’s guy – the kind of buddy you’d grab a beer with and listen to Styx. As Billy Madison kicks off, however, he needs a bit of toughening up; he’s the son of privilege, whose father is no less than Mike Hammer himself, Darrin McGavin. (Also known as the old man from A Christmas Story.)

It’s as if Billy Madison is codifying the unpolished Sandler – previously seen on SNL –turning him into the durable movie staple in later (safer) comedies like Big Daddy and The Waterboy. On a meta level, Billy Madison sees its protagonist graduate… while letting its star succeed on a level rivaled by few comedians, ever.

Billy Madison is at its best when the comedy feels loose and anarchic. And, unlike Happy Madison’s recent output, the film feels strangely deliberate in its stupidity –a devil-may-care attitude toying with what’s conventionally funny. The ’90s were a place for high concept comedies – Eddie Murphy and Mike Myers in fat suits, Jim Carrey possessed with magic powers. And then there’s Sandler, smirking weird lines like “That’s assault, brotha” and “Stop looking at me, swan.”

With his goofy delivery, and deep-seeded anger, Sandler was tapping into the angst of disaffected suburban teenage males – think Jackass or early Eminem, less Robin Williams.

One of the comedy’s best moments involves the menacing O’Doyle clan, cartoonish tormentors to Billy who punctuate their abuse with the celebratory “O’Doyle Rules!” In Sandler and co-writer Tim Herlihy’s surreal movie universe, the attacks are arbitrary… as is the family’s eventual comeuppance. In a movie like Billy Madison, justice is doled out eventually, in characteristically strange fashion.

Sandler anchors all this with youthful abandon, in contrast to the hazy indifference seen today, years after his brand became an industry.

Like now, Sandler surrounds himself with an assortment of silly co-stars, most of whom had been colleagues on SNL. Chris Farley has a brief but memorable role as the school bus driver (“Good, great, GRAND, WONDERFUL!”). Former Weekend Update anchor, the deadpan Norm Macdonald plays one of Billy’s slacker pals. And Norm’s Update co-writer Jim Downey is responsible for Billy Madison’s most memorable moment:

It’s also worth noting Billy Madison initiated two key trademarks of the Sandler universe. First, the love interest whose names starts in V. Here it’s Veronica Vaughn, to be succeeded by Virginia Venit (Happy Gilmore), Vicki Vallencourt (The Waterboy), Vanessa (Big Daddy) and Valerie (Little Nicky). The second is the Steve Buscemi cameo. Co-stars in 1994’s Airheads, Buscemi has since popped up in later Sandler comedies: The Wedding Singer, Big Daddy, Mr. Deeds, I Now Pronounce You Chuck and Larry, Grown Ups, Hotel Transylvania and Grown Ups 2.

Such are the quirky hallmarks of an Adam Sandler film: Steve Buscemi and girls with the name V. You can see why this quixotic universe –positing Sandler as a misunderstood underdog—would eventually grow stale, sending the actor into more dramatic fare. Ironically, the most successful role Sandler ever mastered was in PT Anderson’s Punch-Drunk Love, a serio-comic adaptation of the Sandler character. (At the time, the project was rumored to actually be an adaptation of “The Denise Show,” fittingly.)

This Sunday is #SNL40, the 40th anniversary special for Saturday Night Live. Sandler remains an outlier in the show’s history, particularly among the list of attending former cast members. Never an impressionist, he wasn’t right for political or pop culture roles better suited for Dana Carvey or Phil Hartman. He lacked Mike Myers’ knack for characters, or even David Spade’s biting sass.

Still, as PT Anderson rightly observed, there was something dangerous and compelling about Sandler in his prime. It was this oddness that makes Billy Madison a success, and defined the comedian’s best work.