I'm sure you are are aware of the podcast "How Did This Get Made?" It's a podcast in which a group of very funny people discuss and dissect some of the worst films ever made, and attempts to answer that question. If I were to add a movie to this list, it would be Dan Akroyd's directoria debut "Nothing But Trouble", which pretty much defines that question.
Financier Chris Thorne (Chevy Chase) meets up with a lawyer (Demi Moore), and the two decide to go on a business meeting. On the way, they stop by a town in the middle of jack squat, and are "arrested." However, things aren't what they seem, as they soon find themselves under the thumb of the despicable and ugly as sin Judge Alvin Valkenheiser (Akroyd), whose courthouse and prison are filled with oddities such as Dennis (John Candy) and his sister Eldona (Candy again), a hideous man/baby (Akroyd again), and various deadly traps.
There isn't a single damn thing about "Nothing But Trouble" that works. Everyone here is awful. Chase is at his smarmy worst, Akroyd is obnoxious as hell, Moore is a blank slate and Candy is basically told to be a grotesque buffoon. None of it is scary or funny. It lives in a paradoxical world in which it labors under the delusion that it's hilarious and that it's audience will be stupid enough to think it's funny. It's mostly just disgusting, with the Judge having a decrepit nose that looks like a penis and the sight of giant, filth ridden babies showing up for...well, because Akroyd thought it would be funny for some reason.
If anything, this is a movie that wants to be a grotesque blend of horror and comedy, and ends up being just plain grotesque. It's got plenty of gross out moments, but none of them are amusing. They are just gross. The other moments (the Judge dancing to Hip-Hop music, Chase being an insufferable little twerp, Eldona having a crush on Chase) are plain insufferable. Everything about it is a painful experience from someone who should have known better, but didn't.
Thankfully, audiences were mostly smart enough to avoid it (it cost $40 million and only made about $8 million total), and it was the first (and probably biggest) nail in the coffin for Akroyd's career in film, as it never recovered from it. I'm not going to say he deserved it-most don't deserve to have their careers ruined by a horrible flop, even if they were responsible for it-but that fact that it represents Hollywood indulgence at it's worst (and many reasons more) make me glad it did bomb.