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1. Dolores Umbridge (The Harry Potter series, J.K. Rowling). She dresses in pink; she collects plates with pictures of kittens on them; she never speaks but in a soft, girlish, over-polite voice; and she made Harry carve the words "I must not tell lies" into his own flesh—because he refused to deny the truth. While she didn't kill as many people as Voldemort, she was much more maddening. With Voldemort, at least you knew what you were getting. (AK'd.) Umbridge was a cold-blooded, legalistic, cheaply feminine sadist.
Right, so she's going to be hard to top. Here are a few others, though.
2. Tom Sawyer (The Adventures of Huckleberry Finn, Mark Twain.) I don't remember much of Tom from the book bearing his own name, but he made me want to throw things at the end of Huck Finn's. The Duke and the Dauphin also deserve mention here, but they were passive irritations who bored me to the point of angst. Tom and his calculating mischief were active sources of distress.
3. Lucinda (Ella Enchanted, Gail Carson Levine). Prone to giving magical gifts that sound nice but carry serious consequences, Lucinda spends most of the tale blissfully blind to the down side of her largesse. Her eventual shame almost made me leave her off the list, but it doesn't change what she did to those giants.
4. John and Fanny Dashwood, Lucy Steele, and Mrs. Ferrars (Sense and Sensibility, Jane Austen). I couldn't pick. Fanny is mean-spirited and John is an idiot. Lucy is manipulative. Mrs. Ferrars is an unfortunate combination of arrogant, small-minded, and heartless. Lucy plays the most direct role, but they all compete to be the most unfeeling.
I would put Pride & Prejudice's Mr. Collins on here, too, if he weren't so comparatively powerless and stupid as to be more comical than anything.
5. Mrs. Norris (Mansfield Park, Jane Austen). Proof positive that favoritism is a bad idea.
6. Vronsky (Anna Karenina, Lev Tolstoy). For all that her husband wasn't appealing either, Anna's adultery might have been a touch more emotionally comprehensible if this guy had had even one redeeming quality. I hope he was handsome, because he struck me as neither good-natured nor good-hearted nor intelligent nor even really manly. Maybe riding steeplechasers made him look manly, but for him, even that was a form of indolence.
7. Matrim Cauthon and Fortuona Athaem Kore Paendrag, whenever they're apart (The Wheel of Time series, Robert Jordan and Brandon Sanderson). Without Tuon, Mat's a selfish skirt-chaser. Without Mat, Tuon is a dispassionate ruler with no shame about her penchant for making collared pets out of Aes Sedai. Also worth mentioning are all the Whitecloaks, the Sea Folk at any bargaining table, and Berelain for her attempts to break up Perrin and Faile.
8. Denethor (The Lord of the Rings, J.R.R. Tolkien). The middle of a world war is a really lousy time to go crazy and nearly kill your own rather important son. Grima/Wormtongue also deserves the demerit here.
9. The Thénardiers and Javert (Les Misérables, Victor Hugo). In the musical, the Thénardiers are sometimes comic and Javert is sometimes sympathetic. Not quite so much in the book—at least, not to my memory. The former are so cruel in their selfishness, and the latter so relentless in his legalism, that I didn't like being around them at all.
10. Erlend Nikulaussøn (Kristin Lavransdatter, Sigrid Undset). I have never detested a protagonist's love interest like I detested Erlend. The man was selfish and thoughtless and had no self-control. I lost much of my sympathy for Kristin when she fell in love with him, which meant that I spent half the book frustrated with her, too.
Not the most cheerful topic, but perhaps a rather cathartic one. I'm sort of shocked at how many judgmental statements I just made, truthfulness notwithstanding. :)
Which characters do you find most frustrating?