1992's live-action/animation hybrid Cool World is the most juvenile kind of edgy Nineties nonsense, the kind that takes something wholesome and something sordid and self-consciously mashes them together just for the same of having done it. In this case, it is a movie whose animating principle (as it were) is to ask the question, and ask it with an appropriately hostile sneer, "what if the cartoons fucked?" Except it wouldn't say "fucked", since one of the other most Nineties things about Cool World is that it was, by studio mandate and the peccadilloes of its most prominent star, neutered down to a PG-13 rating that robs it of its only real hope of being actually interesting.

On the other hand, I would not want to necessarily accuse Cool World of being insincerely edge just to seem hip. "What if the cartoons fucked?" was, after all, a question near and dear to Ralph Bakshi's heart, and this was a Ralph Bakshi feature, however diluted. Bakshi never even slightly hid how much he disliked the finished version of the film, which he felt had been betrayed by producer Frank Mancuso, Jr; hell, by the time the film was in production, it had already gone through some nasty arbitration where Bakshi and Larry Gross were denied screenwriting credit on a full rewrite of Michael Grais & Mark Victor's original concept, leading to bad blood even before Mancuso demanded a third iteration of the film to secure that doomed teen-friendly rating, for an audience that never came. Thus it was that that the idea which enticed Bakshi to make his return to feature film animation, nine years after the barbarian fantasy Fire and Ice, immediately sent him back into willing exile (he has not produced a theatrically-released feature since, only shorts and TV work, including some live-action).

Bakshi and I don't agree on too many things, but we agree on this: Cool World is a compromised piece of crap. It barely coheres as a story at all, starting out as a meanspirited film noir pastiche populated with a variety of cartoon styles from the '30s through the '60s, and ending as some sort of half-assed fantasy about opening a hellmouth over the Las Vegas Strip. Along the way it has two different protagonists who feel like they're in two different stories drawing from two different genres. The first of these protagonists we meet is Frank Harris (Brad Pitt, who is very lucky that he already had A River Runs Through It in the can when this movie bombed upon release; it's not hard to imagine this cutting off all that post-Thelma & Louise career momentum), who has just returned home from World War II to his beloved mother (Janni Brenn-Lowen) in Las Vegas. After winning a motorcycle in a poker game, he takes her on a ride; they cross paths with a drunk asshole and his floozy girlfriend, driving all over the road, and the bike ends up mangled and Mom ends up dead. Frank has a big "noooo" that he nooooos so hard that it somehow interferes with the experiment being run by Dr. Whiskers (voiced by Maurice LaMarche), a round-headed cartoon mad scientist trying to open a rift between the "Cool World" and the real human world. Frank finds himself zapped into the Cool World, and Dr. Whiskers has to start his experiments from scratch.

37 years ago, there's another Vegas homecoming: underground comics artist Jack Deebs (Gabriel Byrne), imprisoned for murdering his wife's lover, has just been released. On his last day, he amuses himself by sketching the sexy star of his comic Cool World, a busty blonde named Holli Would - and I cannot begin to over-emphasise how obvious it is that this godawful pun name was chosen just to facilitate the line  "Holli Would if she could", which everybody involved liked so much that not only is it in the film's dialogue, it was the tagline on its main poster. You know, in case you were trying to figure out what level of wit we're talking about here. Anyway, Holli comes to love and tries to grab at Jack; he flips out and assumes it was some kind of last-day-of-prison jitters, but before night is out, as he tastes freedom for the first time, he just sort of accidentally crosses into the Cool World. He doesn't even have to shout "nooooooo" to do it.

Jack will keep hopping back and forth, spending much of the movie in real Las Vegas trying to figure out what's going on. This a godsend to Byrne, who doesn't have to spend all that much time fighting a losing battle acting against the brutishly composited animated characters. Pitt, however, does: Frank has made a career for himself as a "Noid" detective in the Cool World, having not aged a day in 37 years; his current woe is that very same Holli Would (voiced by Kim Basinger), a "Doodle" who badly wants to escape into the real world. And you would too, if you lived in the Cool World; it's a grotesque nightmare of distorted urban imagery mixed with a vision of Hell that would have made Hieronymus Bosch proud. It makes absolutely no sense whatsoever, and for good reason: by the time it came to planning the animation, Bakshi was so done with Mancuso's vision for the project (and Basinger's; she wanted it to be her proverbial "one for the kids") that he decided to just let his very large, very talented team of hand-picked animators have fun with it. So it is that Cool World operates without any sort of logic to it at all - if a bit of business was playful and fun to animate, in it went. And it did so without any worry about what it was doing in the scene, or even in the frame. Frequently, throughout the movie, two characters will just be having a conversation - at least twice in rooms suggested to be private - and there will just be, like, slapsticky stuff going on in front of them, behind them, between them. On one occasion, some of this stuff disappears in the middle of the frame, in the middle of movement. "Sloppy" isn't remotely a big enough word for it.

At any rate, the way for Doodle to become human is to have sex with one, which is why Holli has been trying to pull Jack into the Cool World; Frank is well aware that if she succeeds, it might very well destroy the entire universe. And so that is how we get a movie in which a pin-up girl animated with all the surly fascination with and loathing of female sexuality that Ralph Bakshi could sum up writhes in PG-13 orgasmic ecstasy an unconscionably grainy shot of Gabriel Byrne, resembling something that you might call sex if you were very sad, and very desperate.

The movie after this is at least bonkers, and generally not set in the insanely hideous Cool World; Jack and live-action Holli warp back to Vegas, and as she keeps snapping back to being a Doodle (not her original character model, strangely; she appears as a slutty clown), she concocts a plan to open that hellmouth. Frank fights to stop her; Jack is too blinded by his cock. Eventually, we get a scene which briefly parodies the "Night on Bald Mountain" segment from Fantasia, which is the closest thing this has to a good joke.

It's hard to comprehend how this turned out so bad. Technically, I mean. Narratively, it was doomed from the moment that Paramount decided to green-light a Who Framed Roger Rabbit knock-off starring a femme fatale designed to look like an unimaginative pubescent boy's most vulgar fantasy about the female form and a plot hinging on Brad Pitt as some kind of weird ultracelibate detective platonically dating a different pin-up girl different from Holli only in that she has black hair. But this has a lot of talent behind it - so why is the animation such an ugly slurry of mismatched styles and compositing worse than you could find in live-action/animation hybrids made for pennies in the 1930s?

The obvious answer is that Bakshi just didn't care, and was adopting a shaggy "anything goes" approach. It's not like his films were ever all that aesthetically stable - the four different forms of animation in his ungainly 1978 The Lord of the Rings attest to that. And he always favored a kind of ultra-crude, frantically-scrawled aesthetic in his urban-set stories of sex and squalor, going all the way back to 1972's Fritz the Cat, where he invented "these cartoons fuck" in its modern form. So in principle, Cool World should just be more of the same. But it is so much worse than any of his other features, and I say that as no fan of Ralph Bakshi. I think part of it really is that PG-13 rating: in all of his R- and X-rated films, there's a certain angry hostility to the storytelling that fits the viciousness of the art. Cool World is both angry and hostile, but not in a transgressive way; it doesn't feel like a rule is being broken. It feels sullen and bratty, unable to make any interesting statements about the world or shocking social norms, and so it contents itself with relying on being merely unpleasant. Unpleasant and inept - an especially grueling combination. It's astonishing how much worse Bakshi's poisoned worldview is when even he doesn't seem to believe in it.