First thing I thought of after reading the OP.
Karl Ove Knausgaard’s “My Struggle”
Have you seen the BBC’s adaption of Sherlock Holmes, Sherlock? Although there’s a couple of sympathetic characters in there (first and foremost Watson) the title character is a highly functioning (or . . . not so highly functioning) sociopath.
And you probably read it in 9th grade, but the first thing that came to my mind upon reading the thread title was Lord of the Flies.
That is more like a villain changing over time. I mean I’m not going to give the Joker a pass because I find out he really did have an abusive childhood.
I find true morally grey fiction is HARD, where you have actual flawed but well meaning characters who make understandable bad choices. Far easier to make everyone an asshole or nasty and then your hero is just a few shades lighter than the baby eater.
I disagree. You go from “Ew, he’s having sex with his sister! What a disgusting perv!” to “Huh. He’s struggling with the fact that he’s genuinely in love with his sister and finds it unfair that it’s frowned upon when the ruling family used to do it regularly.” That’s not him as a character changing; it’s the author giving the reader a new perspective on the situation.
How about HBO’s Rome? It was a look at Roman history from Caesar up to Octavian taking power, from the perspective of two relatively low-ranking soldiers. Full of moral ambiguity and protagonists doing morally questionable things. It didn’t do so well in season 2 (compressed a lot into a single season), but overall I think it still holds up.
Excellent pick. The movie, anyway- I never read the book.
My contribution to the thread is The Secret In Their Eyes (movie).
Having just re-watched Glengarry Glen Ross, I think it fits the bill.
The fact that he had sex with his sister didn’t bother me. The fact that he threw a kid out of a tower window did. And no amount of new perspective made me forget that he threw a kid out of a tower window. And in fact he does change after some unhappy experiences and turn into a good guy. Which still doesn’t distract me from the fact that he threw a kid out of a window.
And in fact there are good guys and bad guys aplenty in Game of Thrones (Ok, mostly bad guys). The twist is rather than the good guys generally don’t get to win and the bad guys don’t get their comuppance. But it’s not that morally ambiguous. When character A fights character B, almost every time you know who you want to win (and he generally dies).
The Sopranos. Finest television series of all time.
Both the Dennis Lehane novel Gone Baby Gone and the Ben Affleck movie version are great examples.
The protagonist does the legally and morally correct thing, and loses the most important person in his life as a result… and discovers that everyone would probably have been better off if he’d done the wrong thing.
David Mamet’s play Glengarry Glen Ross actually gets us to like and root for some sleazy real estate salesmen. There’s one we feel so sorry for that we hope he’ll make a big sale, even though we know that to do so, he’d have to rip off some innocent, gullible people.
I recommend the book Vanity Fair by William Thackeray.
I’m not sure that the characters are morally ambiguous though, they are all horrible human beings doing horrible things for selfish reasons.
The ambiguity comes from us caring about what happens to them.
Great series though.
I don’t know if it qualifies as moral ambiguity, but you will finish watching the great movie Doubt still wondering what the truth is. And it has Meryl Streep, Phillip Seymour Hoffman and Amy Adams, too.
Good call- what made the central question more interesting to me is that author John Patrick Shanley is unquestionably a liberal, and that he’s more inclined to like and sympathize with the young, liberal, hip priest played by Philip Seymour Hoffman than with the stern, old-school nun played by Meryl Streep. Shanley also expects his audience to share his sympathies.
That makes it all the more interesting when it becomes more evident that the old nun is right.
Well, I had never watched an episode of The Shield before, but thanks to you guys, I watched the pilot today. Holy shit that was awesome!
…I had no idea Vic was THAT crooked.
I think The Talented Mr. Ripley might qualify for this.
I second Brave New World as the epitomal dystopian utopia.
If you’re looking for books, virtually anything by Stephen R Donaldson. Two of his series (Chronicles of Thomas Covenant and the Gap) feature rapists as main characters, and they’re not all sorry about it. His Mordant’s need books are the only ones with anything like a hero, which is probably why so many people like them best.
And then there’s Peter Watts. Start with Starfish which is free on the web under the Creative Commons license (along with three other early novels and many short stories). If anyone doesn’t appear ambiguous enough at the end of Starfish. Watts also deserves honorable mention for citing scientific papers in his end notes.
Star Wars The Clone Wars TV show:
Fully explores the fact that the Republic and the holy Jedi are essentially using slaves as cannon fodder and also explores moral issues of war. If you hate scifi or Star Wars stay away.
Blade Runner movie:
Our protagonist hunts down runaway slaves, nuff said!
Dirty Dozen movie:
I highly recommend this movie if you’ve never seen it, I don’t want to spoil anything but the set up is your run of the mill action/war movie with a lovable gang of misfits.
And even though the movie tells you from the start what they are going to do, once you see it happen…it is sickening and you want to save the “villains”.
Dollhouse TV show:
I can’t think of a single character in this I’d describe as either a villain or hero, scifi premise about being able to download and upload minds and consciousness into people. The plot if WAY deeper than it appears in early episodes.