Best movies/books/shows for moral ambiguity?

I’m a new mood, dopers. I’m looking for some movies/shows/books that thrive on moral ambiguity. I really want something I can sink my teeth into - just a whole mess of a situation and no one is particularly a good guy. I want to try to figure their motives and try to draw conclusions on who was right and wrong (without the author telling me).

This is what I really loved about the Wire and, in a less grand sense, what I liked about Breaking Bad, west wing, and True Detective. House of cards has it going on too, but I think frank is more obviously sinister but it’s so delicious that we eat it right up.

As far as movies go, the best ones that I recently remember are Blue Valentine and The One I Love. Both just weaved in and out so much that it was hard to remember if this person or this person was the “good person” or even if what they were doing

I got a nice weekend coming up and would kinda prefer movies since they, you know, don’t have such as huge of an investment, but I’m down for any suggestions as far as TV/Movie/Book.

Btw - a protagonist with a drinking problem or remorse about all those Russian mobsters he just killed doesn’t count. That just a conflicted person and is in literally every movie and tv show now.

I’d recommend The Shield. It’s about a corrupt cop (Vic Mackey played by Michael Chiklis). The show never denies that he’s corrupt but it attempts to show how he justifies his corruption to himself.

Great username/OP combo. :wink:

This article onmoral ambiguity in print and on screen might be helpful, though it’s more about specific characters than entire works.

I’m going to be hated for mentioning this, but Nabokov’s book Lolita is intentionally morally ambiguous from the narrator’s point of view within the story, until the end, when the narrator realizes how wrongly he had behaved.

If you are at all interested in fantasy, try anything by Joe Abercrombie - start with the First Law trilogy. Moral ambiguity abounds. All of the characters are morally ambiguous.

One of the point of view characters is a professional torturer … and he’s relatively sympathetic!

Huxley’s Brave New World.

Maybe?

The recent BBC series Utopia might not be the first thing to spring to my mind, but for my money, it has one of the most interesting moralities out there, at least in series 1. Without giving away too much, when you finally get the reveal of what the evil conspiracy is up to, you can’t help but feel that they just might have a point. In the second series, sadly, they back off of this and end up with a much more straightforward good guy/bad guy situation.

First thing that came to mind is Clint Eastwood’s (awesome) “Unforgiven”

Have you read The Goldfinch? It’s a pretty big commitment, but full of moral ambiguity. I just finished it yesterday and found it very satisfying.

Boardwalk Empire: is Nucky, good? bad?

Inception

Michael Moorcock if you’re into fantasy.

I thought of another Eastwood film, “Million Dollar Baby”.

Also, most Tarantino films are filled with bad protagonists doing bad things - Kill Bill, Pulp Fiction, Reservoir Dogs.

In a similar vein to what the OP is looking for are films that I call “movies where everybody ends up worse than where they were when the film started.” In that vein I offer:

Mystic River
The English Patient

But, really, if you want to see a film where everybody ends up worse and with a morally ambiguous ending, you can’t do worse in modern mainstream American film than Million Dollar Baby. You think it’s heading to a typical “underdog triumphs over all” resolution and then… awwww, fuck. And it won the Oscar for B. Picture, so it’s got that going for it, and, more bizarrely, it earned over $100 million domestic. Go figure.

Ira Levin’s works are full of moral ambiguity, especially his little known This Perfect Day.

You also might want to try Errol Morris’s documentary The Fog of War which could make you think “Hey, Robert McNamara isn’t such a bad person after all. Wait, did I just say that about the head of the Dept. of Defense during the Vietnam War and the World Bank when it saddled third-world countries with hundreds of billions of unsustainable debt obligations?”.

Getting on board the Jamie Train in Game of Thrones will really have you questioning your fetish for redemption arcs.

I’ll see those, and raise you “High Plains Drifter”.

Also, the OP may want to check out the HBO series “Game of Thrones”.

That’s a good one. The Game of Thrones books are notorious for twisting things around. Martin spends a couple of books making Jaime out to be one of the most horrible, monstrous people in the world, and then pops you into his head and makes you relate to and even like him somewhat. There are very few real “good” or “bad” guys in that series.

S.M. Stirling’s Domination of the Draka series. The reader spends enough time inside the heads of Draka characters to at least get where they’re coming from.

Try Woody Allen’s Crimes and Misdemeanors.

Nabokov Lolita. Wrote the book on moral ambiguity, and one of the greatest and most entertaining books ever written in English.

I recommend both the book and movie versions of A Simple Plan. The moral questions raised by the characters’ actions are haunting. I kept asking myself whether or not I would proceed down the same paths if given the same circumstances.