Altman & Kubrick are two great filmmakers known for their departure from conventional Hollywood morality. In Altman & Kubrick's universes, the good guy doesn't always get the girl, the bad guy doesn't always get punished, and the crooks don't always go to jail.

But the funny thing is you can't accuse either of them of being amoral storytellers. Sure the characters and action don't give us any satisfying karmaic closure, but I'd say even more powerful is the unsettling feeling we're left with through their storytelling. This forces us to interpret our own moral conclusions, and that's more effective than being preached at. In Clockwork Orange, the rapist/murderer happily being spoon fed in a comfy bed is designed to make us feel like something's wrong with the picture. And I think this is the most powerful form of morality tale.

So who was better at it, Kubrick or Altman?

I haven't seen all their respective works, but I'm leaning toward Altman. This is because I feel like Kubrick goes so deep into the nightmare that we lose our personal connection. Back to Clockwork Orange, that story is so bizarrely nightmarish that it's almost like a horror story that doesn't apply to our lives. But a film like Short Cuts is instantly relevant on a personal level, mainly because the characters and situations are so ordinary. Each audience member will associate with at least 1 character or situation. And that's what makes it more effective when we see bad things happen that go unpunished and open-ended.

(Spoilers below)

I think the most effective ironic-morality-tale is the story about Lily Tomlin hitting the kid with her car. A classic morality tale would punish her character while giving some sort of victory to the injured family. But here the opposite happens. Lily's character is one of the only ones who gets a happy ending. She never even has a moment of reckoning because she never finds out what happened to the kid after. So this entire story is like an open wound that sits with us after the credits roll.

At the same time, Altman gives us a few doses of classic morality melodrama to contrast against the open wound. The cop abandons the dog, and his life is miserable until he finds the dog and brings him home. Almost a comic book morality tale right there. But I think Altman did this on purpose so that we feel the contrast between the Hollywood ending vs other stories where things don't tie up as neatly. The contrast is so effective that we start to question if the cop even has real closure, or is it silly to think him fixing his 1 error would result in a happy family. The cop's "perfect" morality tale itself becomes ironic.

So yeah, my vote goes to Altman for best ironic moralist, although Kubrick is a close second. I think Terry Gilliam is in the running too, but Gilliam goes so far into fantasy/nightmare that we completely lose the connection to our personal lives. Altman keeps it real.