Mark Zuckerberg - at least how he was portrayed in The Social Network.
Mattie from True Grit. She was annoying, bossy, and screwed over a small business owner in the first scene. Didn’t care for her at all.
He was my first thought. I loved the books when I read them in high school. 20 years later, I decided to re-read them, and I couldn’t even get through the first book, almost entirely because I couldn’t stand Covenant.
I tried, very hard, to watch Mad Men (it’s about the industry in which I work, after all). I just couldn’t get past the fact that I hated every single character.
That’s not true, though. In the very first Flashman book:
He unrepentantly rapes one woman (though he adds that he doesn’t much enjoy rape - too much trouble), and beats another for denying him sex
No sympathy whatever for Benjamin Braddock (“The Graduate”); all of my sympathies are with Mrs. Robinson, ultimately the real victim in the story.
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I enjoyed it too but weirdly I found myself really loving all the characters. I’d see them do all these terrible things and then sort of mentally justify it to myself. Well, maybe not Ralphie…
Walt from Breaking Bad. I could understand his motivations early on, and the internal conflict he experiences is always interesting, but he’s very often a terrible, terrible person.
I just finished reading a YA novel called The Marbury Lens, and I think you’re supposed to like the main character, a teenage boy. He was abandoned by his biological mom, and raised by her parents, who obviously care about him and spare no expense to give him a nice life. He says at one point in the book that he has no more feelings for them than if they were pieces of furniture. Well, fuck you too, Jack.
I think Barry Lyndon fits the bill - a philandering, hot-headed asshole who fancies himself far too much. He’s also the textbook unreliable narrator.
I’ve got to disagree with Silent Kal about Vic Mackey. While he is undeniably an evil man, his motivations are good.
There is a flashback episode that shows his original team succumbing for the first time to the temptation to break the rules, vowing they will only do it “just this once.” I find him very sympathetic as a man who wanted to serve justice, care for his family, and make the streets safe for innocents, and ended up paving his own way straight to hell.
Flashman is much worse in the first book than in subsequent ones. I think Fraser began to like the character and toned him down later on. As you indicate, his behavior in the first book is quite abominable. In the later ones he’s mainly just exploitative and cowardly, rather than gratuitously sadistic (though there are some exceptions).
Same thing happened with Al Swearengen in Deadwood. He had virtually no redeeming characteristics in the first season; later he became more a Machiavellian politician than a monster.
Everybody onscreen on Seinfeld.
I realize the concept of the show requires annoying people to say and do annoying yet funny things, but for me the annoying overwhelms the funny.
Heh, in the second book:
[spoiler]He tortures an opponent, then swears to “let him go” if he tells him the info he needs - and he does - over a cliff! 
Mind you he had it comming. [/spoiler]
Though in general, I’d agree - he’s not as horrible in later books. Excluding that incident in Redskins already mentioned …
My own example is The First Law trilogy, and to an even greater extent, Best Served Cold, both by Joe Abercrombie.
In the latter book, literally every major character is horrible, to the point of being unredeemable monsters.
What I love about this criticism is that the characters on Seinfeld are almost always in the right. Yet, they’re labeled as monsters in almost everything they do.
I would not call them monsters. Just annoying.
Though he didn’t start out that way Richard Rahl of the **Sword of Truth **had me totally disgusted by who he was by the end of the series. He was a murdering totalitarian psychopath who would have been the villain of any other series. It was only the fact that the actual villain of the series was a cartoonishly evil monster that Richard was in way shape or form the hero.
Nothing like reading 4 pages of Richard talking about how everyone has to come to their own conclusions and think for themselves but if you come to any other conclusion then his you’ll have to be murdered on the spot because you’re clearly an irrational person that hates life, love and hope.
The weirdest thing was is that in the hands of a skilled writer Richard could have been an interesting morality tale about how if you fight evil you can become as monstrous as what you fight, but no all of this crap is played totally straight.
Edit: oh and his wife is actually worse than him. Just to give you an idea she threatens her half sister with gang rape because she wanted to withdraw from the alliance she never agreed to and become neutral. She also approved of the straight up murder of her half brother who had come as a peaceful envoy to pass along this news.
I tried to edit this in but missed the window. I repeat again in case you don’t believe me that this is played straight. This isn’t Tomas Covenant who we’re supposed to hate or is supposed to be a jerk like Flashman. These are the heroes that the author clearly thinks are wonderful people we should look up to and believe in. It’s absolutely surreal to read pages of Richard cutting down unarmed peace protesters and feeling GOOD about himself for removing a ‘threat’ to the world.
I think this is more true in Curb Your Enthusiasm.
And let’s add Six Feet Under. I stopped watching it after the first season because the characters were pretty much all assholes, but I decided to give it another shot this year because one of my current favorite actors played Gabe in the first two seasons, and I’d all but forgotten he was on the show. In viewing attempt #2 I made it as far as when Gabe disappears because the rest of them are still a bunch of assholes, and I didn’t care what happened to them.