After perfecting his comic persona in Billy Madison, and relaxing it slightly in Happy Gilmore, Adam Sandler experimented with dissociating its two component parts in his next two films. Where he regressed even further into toddler tantrums with The Waterboy, he explored his sentimental side in The Wedding Singer, which remains his only really viable attempt at a romantic comedy to date. In both films, he built further on the everyman persona that made Happy Gilmore so successful and, in doing so, moved further away from the anarchic antisociality of Billy Madison. While he tried to do the same thing at various times in his middle career, these two films were where it ultimately worked the best, and together with Happy Gilmore and Billy Madison, comprised his golden age – an incredible mid-late 90s run.

The Wedding Singer was also one of the first 80s nostalgia pieces, clad in bright pastel colours, flamboyant fashion choices and over-the-top hairdos. Sandler plays Robbie Hart, a wedding singer whose fiancée leaves him at the altar just as he meets Julia Sullivan, a waitress played by Drew Barrymore, who is also having issues with her fiancée Glenn, played by Matthew Glave. In some ways, Christine Taylor steals the show as Holly, Julia’s cousin, especially since her comic persona is big enough to withstand all the slut-shaming thrown her way (and there’s a lot of it). Still, Sandler and Barrymore really shine too, especially since Sandler would never again be able to acknowledge a female co-star in quite the same way as Barrymore, so there’s something fascinating about seeing the beginning of their working relationship here.

This 80s backdrop really works to Sandler’s advantage – especially with his chronic inability to generate comedy from dialogue, repartee or anything resembling conventional wit. He spends most of the first act behind the microphone – first singing, and then, when his fiancée leaves him, in a more bitter mode that foreshadows his later brand of variety-show stand-up. That’s not to say that his singing completely substitutes for the dialogue, but it does take some of the pressure off, especially since the 80s soundtrack does a lot of the heavy lifting too. At times it’s like watching a movie with an 80s radio station on in the background, as Sandler pumps it wall-to-wall with Top 40 standards, filling in his soundtrack as clinically and mechanically as he includes product placement. In other words, The Wedding Singer is Sandler’s effort to both rehabilitate and draw on Going Overboard, his only 80s film, about an uninspired stand-up comedian, to create a kind of belated 80s teen classic for the late 90s. 

As a result, The Wedding Singer is Sandler’s one and only true bid at being a teen heart throb, and it works surprisingly well, at least in the first and third acts, since this is very much a three act film – a systematic exploration of what it might take for Sandler to sufficiently socialise to plausibly fill the role of romantic lead. For the first act, he works surprisingly well in this sweet, mild, ingenuous mode, partly because he’s a man-child at heart, meaning that innocence comes naturally to him. The Wedding Singer doesn’t just draw on the ingenuous side of Sandler’s earlier films, however, but adds a distinct new ingredient – a hokey, old-timey quality that seems to extend back much further than the 80s, to the golden age of Hollywood. Watching these early scenes, it’s not hard to see why Sandler adapted Mr. Deeds Goes to Town in the early 2000s, since the hallmarks of that Gary Cooper persona are present here.

For a while, this gentle flow works quite well, but it quickly develops a maudlin edge when we segue into the second act, which starts with Robbie losing his fiancée and striking up a friendship with Julia. This act feels like the start of Sandler’s subsequent victimology, since it’s easily the most self-pitying moment in his work so far. In Sandler’s earlier films, side characters had a tendency to over-disclose to him, and (supposedly) shove their desires in his face, but it’s taken up a notch now. In The Wedding Singer, Sandler feels oppressed, bullied and victimised by the sheer existence of bodies and desires outside of his own immediate urges. For all the film’s niceness (or because of it), there’s more body-shaming than in Sandler’s other films combined, and a particularly manic obsession with fat-shaming women.

This marks the start, then, of a particularly toxic Sandler brew – punching down while presenting himself as a victimised mouthpiece for saccharine decency. During this second act, Sandler pairs his most sadistic comedy with his most self-pitying protagonist, making for the least likeable character in his work to date, if only because he makes such a maudlin effort to be likeable. In Sandler’s hands, the key trait of the everyman is arrogating victimhood as his right and privilege, especially when it comes to women. Beyond a certain point, Robbie feels victimised by women having an appetite for anything other than him, as evinced in a scene that takes place in a cake shop, where the main characters all pass a piece of cake to each other, only for Robbie to be faced with his most primal fear – an unknown woman’s mouth, yawning open in front of him. In his earlier films, this meant that Sandler could only deal with women as fantasies or as mothers (or ideally grandmothers) but here even the grandmother is presented as a total freak, just because she dares to mention intercourse frankly to Robbie.

At heart, and for all his gross-out comedy, Sandler is a real prude, and that really comes through in this second act. He’s a Republican in spirit outside of his own bodily desires (that’s usually what being a Republican entails), presenting female desire as inherently monstrous whenever it doesn’t explicitly light on him. This misogyny creeps up on you gradually, though, since virtually every woman in the film is attracted to him in some way, and even then usually shamed for their desire. Old women, trans women, the fiancée who dared to imagine something better – everyone is fair game, as Sandler becomes the voice of histrionic macho monogamy, policing everyone else’s desires whenever they don’t satisfy his own perversions.

At the same time, this second act, which is the talkiest part of the film, reiterates that Sandler can only do dialogue by dialling back his energy to the point where he’s effectively sulking the whole time. This is his version of naturalism – a single sustained pout – and it’s not all that different from Paul Thomas Anderson’s reinvention of him in Punch-Drunk Love, which in many ways feels like a continuation of The Wedding Singer. No surprise, then, that his romance with Julia is pretty basic – they bond by talking about weddings, while all they really have in common is that they want to marry someone other than their fiancée. While there’s no doubt that Sandler and Barrymore have great chemistry, I never really believed the rapport here, which is perhaps why Fifty First Dates had to do it over and over again to get it all right.

Amazingly, though, the sheer intensity of this second act burns off Sandler’s antisociality, allowing the film to get sweet again in the third act, when it genuinely approaches the soulfulness of a great 80s romcom. No doubt, the sheer weight of the incessant 80s music plays a part, but this is still a remarkably breathless and romantic conclusion on its own terms. In Happy Gilmore, Sandler discovered that he could only really make his third acts resonate when he pulled back from dialogue as much as possible. Here, too, his romance with Julia blossoms precisely because they have very few scenes together in this last part of the film, communing from afar as they’re on the very cusp of going their separate ways. No doubt, too, the body-shaming is still somewhat there, but it’s absorbed back into the absurdity of 80s fashion, most memorably when Robbie bonds with an airport worker over A Flock of Seagulls.

It’s quite artful, then, that the film ends poised between Robbie and Julia’s two possible futures – in an airplane, en route to Julia’s wedding to Drew, in Las Vegas. The lovers remain distant until the very last moment, and Sandler delays dialogue until the very last moment, removing even the dialogic element of his singing by giving a surprise performance from behind the first-class curtain, and only revealing himself to Julia in the closing seconds. It’s a beautiful ending to Sandler’s effort to self-socialise – and while it’s not always pretty, and while it’s not always true to the anarchic antisociality of Billy Madison, it’s surprisingly touching in these final moments, which feel like a great lost 80s film that only Sandler saw.