My vote goes to All Dogs Go To Heaven by Don Bluth. Supposedly a fun children’s animated feature about talking animals. In actuality, a surreal and terrifying maelstrom of fear, confusion and brutality, and existential questions of life and death, set in an utterly seedy dockside-slum environment straight out of Samuel Delany’s Hogg.
The plot in summary: two dogs escape from a high-security prison by tunneling through the ground, destroying a water main in the process and presumably causing disastrous damage to the facility. Once out, they re-unite with their old boss Carface, who is a homicidal gangster and extortionist who runs an illegal gambling parlor. (“Rat races,” a funny take-off on real-life dog or horse racing.) The whole thing is set in some kind of underground dockside slum with an incredibly low-rent, sleazy atmosphere.
The main character, Charlie, betrays his boss, and in return, is shot to death in a drive-by machine-gunning. He finds himself in heaven. A seductive female dog, some kind of angel, greets him and welcomes him to heaven, but Charlie insists on leaving. He has to go back to earth to take revenge on Carface. He somehow ESCAPES from heaven, makes it back to earth and gets back together with his old crime partner Itchy. Charlie murders Carface, and then Carface himself goes to heaven. Charlie, however, dies AGAIN in the process, but this time instead of going to heaven, he goes to hell! He has a nightmarish experience, thrown around by burning lava and giant promontories of flame, tormented by demons and devils. Somehow he manages to get back to earth yet again, where he is severely traumatized and shaken.
Oh yeah, and there’s a whole subplot about this girl who has the magic ability to talk to horses, who is kidnapped and held prisoner by Carface, who plans on keeping her as a slave and using her talent to predict which horses will win at the races, so he can make money off of them.
I may be messing up the narrative here, because I don’t really remember it all that well after this point. But there’s a Mardi Gras celebration, and then Charlie and his friend Itchy are captured and then serenaded by a gigantic and utterly flamboyant drag-queen alligator (voiced by Ken Page, who also did Oogie Boogie from Nightmare Before Christmas.) I can’t remember what happens after this. It’s all a blur of frightening and bizarre cartoon imagery.
It is also filled to the brim with dialog that is WAAAAAAAY over the heads of any children who might be watching it. Horse-racing jargon, old-time mobster slang, and a musical number which includes the line “jilted by a skirt.” There is not a single child in America, anywhere, who knows what “jilted by a skirt” means.
In short, this is an absolutely badass, awesome movie, but it is in no way, shape or form suited to its target audience. I absolutely loved it as a kid - watching it many times - but I didn’t fucking understand any of it because the atmosphere, the dialog, the moral messages about trying to cheat death or whatever, simply did not compute in my 8-year-old head.
Any other candidates?