Though he technically made his starring debut in the ill-fated, little-seen 1989 comedy Going Overboard, Adam Sandler’s film career really began with 1995’s Billy Madison, his first solo vehicle after rocketing to stardom as a lovable, giggle-prone, guitar-strumming man-child on Saturday Night Live.

In keeping with the persona he developed on SNL and in his stand-up, Billy Madison—which Sandler co-wrote—cast him as an insanely wealthy, belligerent child of privilege who would rather drink and goof around than make a meaningful contribution to society. Billy lives only for his own pleasure until his father, a self-made man, tells his 27-year-old son that he must go through all of grade school and high school again in order to take over his dad’s company.

Billy Madison must be close to Sandler’s heart, because he named his production company Happy Madison after his breakthrough hit and Happy Gilmore, its follow-up. From the perspective of 2015, it almost feels like Happy Madison’s name was a defiant statement by Sandler that he would refuse to evolve beyond the comedy he made at the very beginning of his film career.


To be fair to Sandler, he has intermittently shown an interest in venturing outside his comfort zone, most notably in his riveting dramatic performances in Paul Thomas Anderson’s Punch-Drunk Love and Judd Apatow’s Funny People, but Sandler cannot make a step forward as an actor without following it up by five steps back into his comfy world of adolescent juvenilia.

Twenty years later, Billy Madison now looks like an unfortunate metaphor for Sandler’s film career. Though Billy grows up a little by the end, for much of Billy Madison he is a man of ridiculous privilege who must only do the bare minimum expected of adults in our society—essentially prove himself capable of the intellectual challenges of elementary and high school—in order to maintain his carefree life of wealth and idle pleasure.


That is not an inapt description of Sandler’s film career. As a movie star, writer, producer, and production company head, Sandler is ferociously committed to doing only the bare minimum. This was never more apparent than in the Grown Ups movies, which seem less like films than experiments to determine just how much naked contempt for audiences Sandler could convey before audiences rebelled.

The Grown Ups movies have grossed over half a billion dollars collectively worldwide, but a backlash ensued all the same as audiences that generally flocked to Sandler’s films, no matter how dire, turned on him with a vengeance. In that respect, when a number of Native American extras walked off the set of The Ridiculous Six, his most recent film, and the first film in his four-picture deal with Netflix, claiming the film disrespected and insulted Native American culture and women, there was a sense that they were also speaking for the viewing public.


I have not seen a script for The Ridiculous Six, but I am inclined to believe that it does indeed insult Native American culture. Sandler’s films as of late, with very few exceptions, don’t just offend specific minority groups: They’re pretty much an insult to everyone unfortunate enough to buy a ticket. Sandler may or may not have insulted Native American culture with The Ridiculous Six, but he’s done a bang-up job of insulting American culture with many of the the movies he made before it.

Sandler’s dreadful recent films are so awful that you don’t even need to see them to be offended by them. The mere fact that a movie like Jack And Jill exists, and prominently features Sandler, in drag, talking about how Al Pacino (playing himself!) only wants to play “twister with your sister” is enough to inspire something approaching despair and concern for humanity’s future.


Though Sandler enjoys a reputation as one of Hollywood’s nicest stars and a consummate mensch, his comedy often has a mean-spirited, bullying quality to it. That’s My Boy, for example, turns on the notion that female-on-male statutory rape is both innately hilarious and awesome, assuming that the women doing the molesting are sufficiently hot. That’s a depressingly common sentiment in our society. Underage women taken advantage of by sexually adults are generally viewed, rightly, as victims of unconscionable predators while boys taken advantage of sexually by adult women are viewed as lucky devils whose early sexual experiences merit enthusiastic high fives instead of counseling. But that does not make That’s My Boy any less offensive or cruel.

Despite the odes to working-class life that litter his films—the supporting performances from sports heroes, the product placement for Hooters and Dunkin’ Donuts and his weakness for cheesy arena rock, often of the 1980s variety—Sandler is all about punching down. The butt of the jokes in his comedies are not the wealthy or powerful but the poor, powerless, fat, unsuccessful, and weird-looking. In his films, Sandler is often a 1 percenter at the top of the socio-economic ladder making fun of everybody at the bottom.


Sandler’s long, free ride with the public and Hollywood seems to have come to a dramatic end, however. A man who previously pumped out hits effortlessly has found himself in a prolonged and seemingly permanent downward spiral. As of late, nothing has worked for Sandler. He left behind the sticky sentimentality of his family movies for the hard-R vulgarity of That’s My Boy and it bombed. Sandler reunited with Drew Barrymore, the Julia Roberts to his Richard Gere (in the sense that they starred in multiple romantic comedies that were both incredibly successful and also terrible) for Blended, and it bombed.

In an even more depressing and bewildering development, Sandler seemed to have listened to his critics and last year starred in a pair of small films by arthouse auteurs with impeccable credentials: Jason Reitman of Juno, Young Adult, and Thank You For Smoking, and Thomas McCarthy.


Before he encountered Sandler’s reverse Midas touch—everything Sandler touches these days seems to turn to shit—actor-turned-director McCarthy had an unblemished, if small filmography as a filmmaker. Pre-Sandler, McCarthy established himself as a master of the brilliantly acted small-scale character study with his first three films, The Station Agent, The Visitor, and Win Win.

McCarthy’s otherwise sound instincts make his collaboration with Sandler, the astonishingly awful, surreally misconceived comedy-drama The Cobbler, all the more bewildering. The Cobbler has a premise that would seemingly suit one of Sandler’s high-concept fantasy comedies: The film follows a humble New York cobbler (Sandler) who assumes the identity of the people whose shoes he makes.


If that premise suggests big-budget tomfoolery, the film’s tone is unrelentingly and inexplicably dour, better suited to a harrowing drama than a goofy comedy. And though he has delivered compelling dramatic performances in Punch-Drunk Love, Funny People, and James L. Brooks’ otherwise misfiring Spanglish, Sandler’s performances in The Cobbler and Jason Reitman’s dreadful, hysterical anti-internet drama Men, Women & Children consist primarily of making a sad face.

In light of all of his high-profile recent failures, it’s hard to see Sandler’s deal with Netflix as anything other than a sign of desperation. Netflix reportedly embraced the falling star because his films were particularly popular on its streaming and movies-by-mail services, but even that speaks to the public’s desire to see Sandler movies, if they must see them at all, in a way that does not obligate them to pay inflated ticket prices, or even leave home for the privilege.


But before The Ridiculous Six hits Netflix amidst a frenzy of bad press and low expectations, Sandler will star in Pixels, his most promising vehicle in years. That’s because the film’s premise—aliens mistake a time capsule launched into space in 1982 and featuring video game icons from the era for an act of aggression, and send in an invasion force modeled on characters like Pac-Man and Donkey Kong—both taps into The Wedding Singer star’s love of lowbrow 1980s kitsch (and hits his target demographic right in the generational sweet spot), and, despite being a Happy Madison production, could probably work without Sandler, assuming it does indeed work at all. That is not true of something like Grown Ups, whose premise is essentially “Adam Sandler hangs out with his buddies, and maybe there’s a movie in that?” It’ll take more than the words “starring Adam Sandler” for a movie to succeed in 2015, which is quite a change from years past.

Is Sandler’s downward slide reversible or have the continual insults to the viewing public that represent his filmography destroyed the public’s seemingly bottomless goodwill towards him? If Sandler wants to win back a public that has given him so much, it might behoove him to try to reconnect with the goofy, adorable man-child they fell in love with on Saturday Night Live by touring as a comedian and releasing an album, something he hasn’t done since 2004’s Shh…Don’t Tell. Of course this would entail writing material, but it would also reconnect a powerbroker who often seems terminally out of touch with his fans and life among the non-privileged with the people who made him rich and famous in the first place.


Alternately, it would be refreshing to see Sandler follow in the footsteps of his Grown Ups co-star Chris Rock and make the leap from writing or co-writing disappointing, lowbrow, enormously un-ambitious vehicles for himself to writing and directing an unmistakably personal, intimate movie like last year’s Top Five.

It’s unclear what, if anything, can turn Sandler’s career around, but it’s evident that if he’s going to halt his steep professional decline, he’s going to have to work. The star of Grown Ups is going to have to grow up, and despite what his performances in The Cobbler and Men, Women & Children suggest, that will entail a whole lot more than making a frowny face and abstaining from silly voices.