Adam Sandler had one real shot at playing an adult in Big Daddy and it must have exhausted him, since he doubled down with the most infantile film of his entire career with Little Nicky, which was also his first box office flop. From Billy Madison to Big Daddy, he had a golden run, effectively reimagining the basic co-ordinates of Billy Madison for each new release, but he didn’t get the balance right here – and getting the balance right was critical to his earlier films, since the actual building blocks of his comedy are so repulsive in isolation. And Little Nicky is one of the most repulsive films of the 2000s – grating, revolting and disgusting to an almost aggressive degree, and abysmally worse than any of Sandler’s other comedies before or since.

Strangely, Little Nicky was also Sandler’s first real attempt at a high-concept, plot-driven film, although the details of this plot are pretty telling. Sandler plays Nicky, the youngest son of Satan, played by Harvey Keitel, in one of numerous bizarre cameos throughout the film. It feels like this was the film when the broader acting community finally realised they might hitch their wagon to Sandler’s star, only to arrive at the very moment his star began to fall. Nicky is the “nice” son, so it’s hard for him to compete with his more devious brothers Adrian (Rhys Ifans) and Cassius (Tommy Lister Jr.) when Satan decides its time to bequeath Hell to one of them. After Adrian and Cassius try to freeze out Satan by moving up to Earth, and closing the portal behind them, Nicky follows suit, in an effort to save both Hell and his father.

It’s telling that Sandler can only come off as a nice guy in Hell, compared to other demonic spawn – and Little Nicky is desperate to present Sandler as a nice guy. For the first time, he doesn’t have any real bullying tendencies, relying on moments of demonic intensity in place of his normal temper tantrums, although that also makes this the single most abject instance of Sandler’s victimology as well. In effect, Sandler presents Nicky as developmentally disabled, but not in a sympathetic way, instead evoking disability as degree zero for bullies, and so using disability to once again present his everyman character as the heir all victimhood. Weirdly, Sandler seems to be aiming for cute for long stretches of the film too, even as he stretches for a grandiosity that sees him quoting James Whale’s Frankenstein in one of the key scenes.

Compared to Little Nicky’s education, Billy Madison had an Ivy League experience, since Nicky has to learn the most basic bodily functions and social norms when he arrives on Earth. These go hand in hand with his consumerist education, turning Little Nicky into the most abject vehicle for product placement in Sandler’s early career. Whether because Nicky himself often resembles Popeye, or because Sandler had simply exhausted every fast food chain in his earlier films, barely a scene goes by without Nicky eating, describing or promoting Popeye’s in some way. At times, this product placement is so shameless that it feels like contempt for Sandler’s audience. At other times, you sense a more venal, immediate imperative – as if Sandler were making a case for himself to be the next celebrity spokesperson for the chain.

As that might suggest, Little Nicky is the first film where Sandler’s self-hatred starts to really seethe, along with his hatred of his audience for not expecting anything better from him – or being content with (and even expecting) his bare minimum. Watching Little Nicky is like being punished for ever expecting anything better from Sandler, and it’s rare to see a film that is so actively antagonistic towards its audience. While Sandler’s films always depended on punching down and bullying anyone in sight, that process now extends to the audience, who are expected to ratify his victimhood even as the film itself bullies us into taking its blandness.

As a result, Nicky feels less like a character than an Ali G persona, or a precursor to Punk’d – part and parcel of the pranking craze that took the early 2000s by storm. Sandler is both more and less in character here than ever before, especially in the scenes when Nicky approaches strangers in the street who don’t appear to be in on the joke. These scenes look like they were done impromptu, as Sandler grates on the public in the same way as Billy on the Street fifteen years later. And, to be fair, Nicky is the perfect character to punk unsuspecting passers-by, since he’s too stupid for an actual film, but just right for these kind of fleeting street scenes.

This movement towards pranking signals Sandler’s final concession that he can’t do comic repartee, dialogue or conversation. In his earlier films, he found various ways to work around this lack, and his subsequent stand-up has compensated for it in interesting ways too, but here he simply stops trying. There’s only four types of exchange in Big Daddy, none of which require Sandler to engage in any real comic dialogue, or acknowledge the existence of comic voices other than his own. First, there are telepathic exchanges with Satan and his brothers, although these feel more like internal monologues, especially since Nicky seems to be dubbed so that he can be heard clearly despite his speech impediment. Second, Nicky has conversations with his bulldog Mr. Beefy, voiced by Robert Smigel, although these also tend to devolve into comic commentary from Mr. Beefy, rather than a regular dialogic exchange.

In addition, Nicky has relationships with two humans in the film. The first is with Valerie Veran, played by Patricia Arquette, who puts in a heroic performance, but can’t save her character from becoming the degree zero of the Sandler girl – a female foil who finds everything he does endearing, no matter what. In a different way, then, this romance becomes another monologue, in which Valerie simply reflects Nicky’s words back to him, leaving Nicky’s relationship with his flatmate Todd, played by Allen Covert, as the last hope for connection.

This is actually the strongest part of Little Nicky, since it’s the only place where Nicky’s incongruity, as a demon released back to New York City, really resonates. As best friends, Sandler and Covert already have a strong screen rapport, but this is the first time they’ve been put in this sustained one-on-one situation, and it really works. At times, it almost feels like a brilliant sitcom premise – a great riff on the age-old sitcom situation of an odd couple forced to shack up together as roommates. When he’s staying with Todd, Nicky’s broader demonic characteristics go out the window, and he simply presents as a stranger-than-normal new roommate, not unlike the alien domesticity of Mork and Mindy or Third Rock from the Sun.

Unfortunately, though, Little Nicky won’t allow this part of the film to flourish, since the finely-tuned incongruity of this roommate situation vanishes as soon as Nicky suspects that Todd is gay. In Big Daddy, Sandler’s best friends were a gay couple, played by Peter Dante and Jonathan Loughran, but after rewatching Little Nicky I wondered whether that liberalism had been foisted on Sandler by the studio, rather than coming out of his own comic arsenal. For those same actors now play a hair metal duo who insert themselves into Nicky’s rapport with Todd at every turn, slinging one gay insult at Todd after another, until no trace remains of their roommate rapport, and the mutual curiosity and incongruity of those opening scenes.

This reflects a broader trend, in Little Nicky, towards punching down on gay characters, who are presented frankly as freaks, much as gayness itself is associated with anything that falls outside the film’s crushing nu-metal soundtrack. Along with Todd, we’re presented with a drag queen who recurs in the story for cheap laughs, but in some ways he’s less freakish for being a drag queen than for listening to synthpopo (Stacey Q, to be precise), which remains totally incomprehensible within the film’s aesthetic universe. At times, you wonder whether Sandler is actually afraid of gay men, so desperate is he to present Nicky as normal by comparison, although the fact that Nicky is demonic spawn makes that a pretty weird project.

Many of these repulsive ingredients were there in Sandler’s earlier films, but at least you could be distracted by the soundtrack, which rotated through hits as economically as Sandler placed products. Here, however, it’s all nu-metal from start to finish, while the film as a whole is like the front cover of a nu-metal album– grating, grotesque and plain gross all at the same time. Sandler himself always leaned towards a certain abject self-presentation, but here there are more lurid set pieces and disgusting images than ever before. It’s so relentless that I actually felt quite nauseous watching it – it put me off my dinner – and had a headache after.

In other words, Little Nicky is Sandler embracing his inherent ugliness as a comedian – the point where he gives up trying to be funny and just aims for disgusting. Whether it’s the endless CGI of people being pulled out of other people’s orifices, or the weird prosthetic set pieces in Hell (including Rodney Dangerfield fondling breasts transplanted to a demon’s head), this is the Citizen Kane of sheer repulsion. The grossness even extends to the product placement, in one of the final scenes, when Nicky attempts to make amends with Satan by bringing him an enormous bucket of Popeye’s that waddles along on outsized chicken legs.

Sandler tends to counter these repulsive tendencies with cloying sentimentality, and Little Nicky is no exception. The revolting aesthetic of the first two acts paves the way for the most saccharine conclusion of his entire career, as we discover that Nicky’s mother was an angel, played in a heavenly interlude by Reese Witherspoon. Upon recognising his angelic lineage, Nicky sets out to do good, sending out rainbow beams from his eyes that undo the work of his father and brother, but also tacitly redirect the rainbow flag away from gay people, who remain too revolting even for the film’s aesthetic of repulsion. In the end, gay people are condensed to Hitler, a recurring character during the Hell scenes, while Nicky’s brothers are finally punished by being inserted into Hitler’s rectum, in the concluding set piece of the movie.

The final note of Little Nicky, then, is exhaustion – total and utter exhaustion. I was waiting for the film to end ten minutes in, so by the time the end credits roll I was barely conscious. At only eighty minutes, it’s the shortest Sandler film so far, but it feels like the longest, and sinks even lower than Going Overboard, which was unwatchable for long stretches, but never as aggressive and antagonistic towards its audience as Little Nicky. While the heavenly scenes look just as you’d expect from Sandler – that is, like a beer commercial – his version of heaven also has a more unusual bent. In Heaven, the angels watch Felicity, Chubbs makes a cameo after passing away in Happy Gilmore, and Reese Witherspoon seems to be in dress rehearsal for Legally Blonde, which was released the following year. Heaven is other films – any other films – while Hell is the Happy Madison house style, which hates itself into the ground here.