Ship It by Britta Lundin has Tess, who would be considered a Loony Fan in most other books. She's a fan who's allowed to travel with the crew from her favorite TV show, Demon Heart, and decides to make her favorite ship canon. She reveals her girlfriend's fandom interests to her class without her consent and she hijacks the creator's twitter account. When one of the actors in the show reveals that his father beat him, she writes a slash fanfic that mentions that. While she does apologize, it doesn't justify her behavior.
George and Harold from Captain Underpants can come off as that in the earlier books. They are said to be good kids who simply don't like their school. However, a lot of their pranks can come off as needlessly disruptive and cruel. For example, in the first book, they deliberately sabotage a football game. In the second, they destroy the other students' inventions after being banned from a science fair (which is entirely their fault, since they had glued the teachers and students to their seats last year). In the third, their fake recipe for cupcakes causes a massive mess in the school, and makes the cafeteria ladies quit their jobs. And in the fourth, their mockery of Professor Poopypants causes him to snap and turn evil.
Edward and the Cullens are... well, they don't eat humans. They let their vampire buddies eat humans, routinely show up the Muggles, use their awesome powers for pure personal gain most of the time, hunt endangered animals for fun, and screw up the lives of many a werewolf to get their way, but at least they don't eat humans. The first chapter of Eclipse explicitly describes the Cullens as protectors of human life, even.
Bella gives minimal thought to the innocent people being killed by vampires, unless it's someone she knows. In New Moon, she seriously considers withholding what she knows about vampires from the werewolves because telling them anything would feel like betrayal to the Cullens (even though she knows full well that the Cullens are in no danger from the wolves at all and that helping the wolves learn about the vampires will help them stop Victoria more quickly and thus keep more people from dying).
It's a lot harder to sympathize with Bree Tanner when she shows no remorse at all for committing multiple murders and seems under the impression that she is above laws as long as there is no one to hold her to them. There's also the matter of her and Diego suffering from a severe case of Too Dumb to Live.
Edward Cullen is an abusive boyfriend. He physically stops Bella from driving herself home so he can take her there; forces her to eat dinner with him; resorts to drastic measures to stop her seeing Jacob, such as having his sister kidnap her and sabotaging her truck; and when she gets pregnant with a half-vampire baby, he tries to get it aborted, and offers to let Jacob impregnate her instead, all without telling Bella anything. And in the unfinished manuscript for Midnight Sun (2020), he's definitely genocidal, casually mentioning wanting to slaughter the Quilute tribe due to Jacob daring to speak to Bella because as far as he knew they were defenseless. He also comes across as a school killer, plotting the murders of his entire class so he could get to Bella without witnesses, and later plots getting her at her home in a way that comes across as though he's planning a rape.
In Eclipse, Jacob becomes just as emotionally manipulative of Bella as Edward is, threatening to go into battle and die at one point, unless she proves her love to him. When she kisses him to convince him not to kill himself, he orders her to "do better than that" or else he won't count it. At the end of the book, he's rude to Leah when she tries to talk to him about his feelings for Bella (granted she wasn't exactly gentle, but given that she too had been dumped by someone she loved, his taunting of her was pretty callous) and then abandons his father to go hide as a wolf for a while. In Breaking Dawn, he throws a fit when he learns that Bella intends to sleep with Edward while she's still human. In the second part of the book, when he hears that Bella's sick, he immediately believes that Edward changed her and goes over to kill the Cullens over it (rather creepily dismantling the phone and ensuring that his wheelchair-bound father couldn't follow after and stop him). He seriously considers Edward's offer to talk her into an abortion in exchange for him knocking her up instead. He later tries to invoke an imprint by going to a park and creepily staring at random girls to force it to happen. When Bella gives birth to Renesmee and he thinks she's dead, he goes to kill the baby to avenge her (ignoring the fact that Bella made it clear she was willing to give her life for her child) and was only stopped by imprinting on her. In case you didn't know, "imprinting" is Stephanie Meyer's word for realizing that the person you are looking at is the only person you will ever feel sexually attracted to. This happened when he looked at a new-born baby. From then on, his imprint makes him do countless horrible things in the name of protecting Renesmee, including saying nothing while vampire allies stay in Forks and eat people outside of the town and ordering all of his pack (including newly-transformed young children) to stay behind as cannon fodder while he and Renesmee abandon them all to escape the Volturi.
Zedd is something of a subversion, because while he's a big part of the epic world-saving quests and Richard certainly treats him as a heroic forebear and wise mentor, there are regular asides to remind the reader that he's NOT someone to be emulated or looked up to. Zedd is regularly characterized by all non-Richard characters as being far WORSE than the big bad of the first book (the war between the two being what broke the world prior to the series' birth), and among the characters expressing this opinion is Zed himself. In the Zed-focused short story Debt of Bones, it is heavily implied that his decision to retire to the non-magic portion of the continent had little to do with staying with his family and a lot to do with looking at the path he was on and predicting that it was a matter of a few years at best before he could talk himself into wiping out all life on the planet completely. For bonus points, this is one of the few story elements where Richard is actually presented as being unambiguously wrong about something, making Richard's hero-worship an in-setting example of the trope as well.
Most Bronze Age heroes lack traits that modern audiences would find heroic due to Values Dissonance.
Achilles is a well-known example, since most modern audiences side with the Trojans defending their home and have little sympathy for the pouting, slave-taking Achilles. Another interpretation is that the Iliad isn't attempting to portray Achilles as a hero (in the modern sense of the word), but is rather showing the tragedy that results from a man's unwillingness to compromise in the face of a perceived offense. Not only to modern readers: in the Middle Ages, Hector was generally a much more popular character than Achilles, largely because he was seen as someone who was defending his home and his people. One popular legend said that Durandal, the sword of Roland, a popular medieval folk hero (based on the very real Roland who was one of Charlemagne's dukes), had been the sword of Hector. In the King Arthur tales, Arthur's adoptive father was named Sir Ector, an alternate spelling of Hector (technically, Hector is an alternate spelling of Ector, but whatever). British statesman Lord Chesterfield wrote in Letters to His Son about Achilles: "I dare assert too, in defiance of the favorers of the ancients, that Homer's hero, Achilles, was both a brute and a scoundrel, and consequently an improper character for the hero of an epic poem; he had so little regard for his country, that he would not act in defense of it, because he had quarreled with Agamemnon about a w⸺e; and then afterward, animated by private resentment only, he went about killing people basely, I will call it, because he knew himself invulnerable; and yet, invulnerable as he was, he wore the strongest armor in the world; which I humbly apprehend to be a blunder; for a horse-shoe clapped to his vulnerable heel would have been sufficient." (letter 64)
Jason is another example, whose greatest accomplishments are actually performed by his mistress Medea, whom he promptly dumps when he's done with her. Jason becomes a Fallen Hero for his treachery at the end of his story. Even before he met Medea, Jason didn't really do anything badass. Prior to seducing her, most of the work was done by his much more Badass Crew, which consisted of some of the greatest heroes of Greek Mythology. The only really decent thing he does in the story is to help an old lady across a river. This wasn't necessarily a Values Dissonance thing. Euripides produced Medea in 430 BCE — that makes it clear this was how most of the Greeks felt about the character even a bare few centuries after the origin of the (presumed Homeric) legend. Whether the bronze-age heroes were meant to be unironically heroic or whether modern audiences just missing the sarcasm of ancient Greek poetry is still sort of in question.
Similarly, when Oedipus kills a crazy old man that he meets on the road to Thebes because the guy insulted him, modern readers are likely to consider this Disproportionate Retribution. As a result, the sense that Oedipus is the (mostly) innocent pawn of fate gets somewhat lost in translation when it later turns out that that crazy old man was his biological father, Laius. Though it depends according to the version of the myth as to whether or not Oedipus was being threatened, whether the King had the right of way, whether someone stepped on his foot, or if Oedipus really did just murder a bunch of guys on the road.
Perseus. Yay, he killed Medusa the horrible monster ... that had been a rape victim (in some versions) and was hiding in a cave in the middle of nowhere so she wouldn't hurt anyone and was asleep at the time. Mainly because the host of a party he went to dared him to. Then he goes around petrifying everyone who annoys him. Slightly mitigated in the versions that include the king threatening to forcibly marry Perseus' mother, but Perseus doesn't ask Athene or Hermes to assist with that matter.
Gilgamesh is a tyrant who makes unreasonable demands of his subjects and sexually abuses young women in his kingdom. His behavior becomes so outrageous that the gods craft Enkidu to deal with him. Gilgamesh and Enkidu later become friends and kill the giant Humbaba for no other reason than glory. After Enkidu's death and Gilgamesh's failed search for immortality, he returns to his kingly duties with no further complaints from gods or mortals.
The Canaanite gods Baal and Anat are not nice people by modern standards. Baal conquers multiple cities without batting an eyelash. Anat revels in bloodshed, threatens her father El when he is reluctant to give in to her demands, and generally behaves like a vicious spoiled brat.
Joshua, from the book named after him in The Bible, slaughters the entire populations of thirty-one cities (an explicitly given number) down to the smallest child, essentially just for being in the way. He's little better to his own people, having entire families executed for crimes committed by one member. Much like with Oedipus, the narrative excuses his actions because he is acting in accordance with fate, as God had designated the land those cities were on to belong to the Israelites, which would've made sense to someone of the time, but to modern readers he comes across as a bloodthirsty invader no better, if not worse, than the people he's fighting against.
Theseus, from the Greek myth of the Minotaur, abandons his lover Ariadne on an island, despite the fact that he would never have killed the Minotaur without her. His reasoning? His father and her father, both kings, are sworn enemies and thus their relationship becoming public would be extremely politically embarrassing. She's rescued by the gods in a rare Pet the Dog moment from them, but Theseus doesn't know that. This is arguably not even the worst thing he does, latter he abducts Helen of Troy when she is still a child even by Ancient Greek standards, (ten in some versions, seven in others) with the intention of marrying her when she gets older. He does this almost purely because he feels entitled to have a divine wife as a child of the Olympians. This sparks a war between Sparta and Athens. He's never punished for this, although he is trapped in the underworld for a time as a result of the different but not unrelated crime of attempting to abduct Persephone.
Cameron "Buck" Williams is referred to as an amazing investigative reporter who has won awards. He almost never files reports or writes anything, and when confronted with an international conspiracy that's already killed two people he knows, he... agrees to bury all the evidence if they'll spare his life. Way to go, hero.
Rayford Steele fits this, too. First there's his stringing-along of Hattie Durham, but what really pushes him into Designated Hero territory is the fact that upon seeing a tarmac covered in crashed airplanes, rescue crews, and injured bodies, it never even occurs to him to help.
And the time when he, as the pilot of the Antichrist, knows that the Antichrist is going to nuke millions of people—including the entire population of the city where he currently is—as soon as the plane takes off and gets clear. A hero would face a dilemma in how to stop this: Try to crash the plane during takeoff, which might kill the Antichrist but might fail thanks to Antichrist powers, or secretly try to remain in range of the nukes, which definitely will kill the Antichrist but could be detected, and will result in millions dead but might be worth it. Or assassinate him, or broadcast what he's doing, or something. Rayford, on the other hand, delays the plane so his wife can leave the city before he takes off. Then he takes off so the Antichrist can proceed. This is not after some long internal conflict, or for the sake of staying undercover, or because he thinks stopping the nukes will fail. It's just because flying the airplane is his job. Our hero, ladies and gentlemen: An accessory to murdering millions of people.
Both Buck and Rayford, by working very closely with the Antichrist, helping him constantly, refusing to inform anyone of who he really is, and not doing a thing to stop him, are well past "Designated Hero" and into "Designated Not-The Dragon," which they would be in almost any story.
Then there's Bruce Barnes, who supposedly becomes a model Christian after being skipped by the Rapture, yet when the time comes to make an apocalypse survival plan, it consists of building an underground bunker for himself and three other people, then hiding in it. The notion of helping, or even interacting with, any of his congregation beside the two Author Avatars and Chloe Steele, except on Sunday morning, does not seem to occur to him.
The two authors of Left Behind didn't learn from their mistake when they wrote other novels, as these examples show:
In Edge of Apocalypse, co-written by Tim LaHaye, we get Josh Jordan. A rich businessman who developed an anti-missile system for the U.S. government which doesn't destroy nuclear cruise missiles, but just redirects them and has them detonate there... and refuses to give control of it to the government because he (correctly) guesses that the Democratic politicians will give it to enemies of America. So he demands to have a weapon that can redirect America's own nukes if he decides to, and no one is supposed to notice that makes him look like a Bond villain.
Liu Bei from Romance of the Three Kingdoms... who manages to get away with abandoning his wives and children multiple times, dashing his infant son into the ground since a brave warrior risked his life to rescue the boy, eating a hunter's wife, turning on or abandoning certain "allies" at rather opportune moments, and in the end having a Heroic BSoD, all because he's for upholding the "rightful" dynasty. Some of Liu Bei's actions are so over the top that one has to wonder if the authors (who were writing about events taking place several centuries before their own time) were at least on some occasions subversively critiquing those same cultural values by exaggerating them to the point of the ridiculous. Liu Bei does in the end fail rather ignominiously; even taking into account that Liu Bei had to fail because that was what happened in history, the novel does on several occasions seem to subtly emphasize his failure. For example, Zhuge Liang and Pang Tong are hyped up with a prophecy that any leader who obtains the services of either one of them is sure to win ultimate victory: Liu Bei gets both of them, and he still fails. While the death of Pang Tong before he could do much was arguably bad luck, someone should have told Liu Bei that he had to actually follow Zhuge Liang's advice for the prophecy to work. (Ironically, when Zhuge Liang was newly appointed as military advisor, Liu Bei was the only member of their force to believe in him!)
Several of Rafael Sabatini's protagonists fit this pretty well, tending to be rather Chaotic Neutral characters. For example, the main character of Scaramouche seeks revenge for the death of his friend by an evil aristocrat and ends up as a high ranking member of The French Revolution government and uses this position to cut a swath through France's aristocracy despite the fact he couldn't give a damn about the ideals of the Revolution.
The Discworld discusses this trope in pointing out that professional "heroes", the people who go around slaying the monsters and stuff, are typically just violent and rather dim. Hrun the Barbarian from The Colour of Magic is too dense to be properly afraid in the Temple of the Sender of Eight or on the Wyrmberg -properly used fear being useful to survival techniques such as following useful advice.
Michael Crichton's Timeline ends with the protagonists drugging the Corrupt Corporate Executive, and sending him to past to die of the Black Plague. While he was a fairly unpleasant individual and was more concerned about using Time Travel to make money than actually giving a chance to learn about the past, he does actively work to prevent the tissue-damage caused to the people who do too many trips through the time-machine/teleporter by forbidding one person from doing too many trips, and all the problems result from those who disobeyed him. But since he's a douchebag, it's all right to murder him horribly. Notably, when The Film of the Book came out, his death and circumstances around it were substantially changed.
Abdel Adrian from the Baldur's Gate novelisations by Philip Athans. The writer wants him to be everything positive, but he really can't pull it off. Adrian is treated as the hero even though without being specifically kicked to it he hasn't even the motivation to do anything but booze, womanise, kill random people and possibly kick puppies.
The Sheik, from the novel of the same name. He's an abusive rapist who is initially portrayed as negatively as he deserves, but once the protagonist falls in love with him the book suddenly expects us to think of him much more sympathetically.
Arthur Dimmesdale in The Scarlet Letter seduced and impregnated Hester (she was a married woman, but her husband was disappeared), left her to assume all the blame and humiliation, participated among the people who shamed her and left her with the responsibility of her child. However, he has the sympathy of Hester, the people of Boston and Nathaniel Hawthorne. He does redeem himself, but in the end.
Anita Blake: Anita is a killer, rapist, and ephebophile, and performs the same actions she reviles in others but it's okay when she does them. And apparently the reason all the evil comes to town is that it's attracted to her. In the early books the villains are usually interested in more generic "acts of evil" like eating children and her acts of extreme savagery come off more as the only choice but then she gets more powerful, and subsequently becomes a worse person. Better written it'd be power corrupting but here it earns her designated hero status.
The Orlando of Evangelical literature is the young curate, looked at from the point of view of the middle class, where cambric bands are understood to have as thrilling an effect on the hearts of young ladies as epaulettes have in the classes above and below it. In the ordinary type of these novels, the hero is almost sure to be a young curate, frowned upon, perhaps, by worldly mammas, but carrying captive the hearts of their daughters, who can "never forget that sermon;" ... The young curate always has a background of well-dressed and wealthy, if not fashionable society;for Evangelical silliness is as snobbish as any other kind of silliness; ... but in one particular the novels of the White Neck-cloth School are meritoriously realistic,their favourite hero, the Evangelical young curate is always rather an insipid personage.
The heroes of The Turner Diaries are a group of Western Terrorist neo-Nazis. Even when compared to their Strawman enemies, they are horrible people, as they kill far more innocent civillians. The "hero" Earl Turner might just be one of the most unpleasant fictional characters of all time.
Patch from Hush, Hush is supposed to be a good guy, or at least an anti-hero we can cheer on. This is the same fellow who apparently uses the Abuser's Handbook as a guide for dating Nora and at one point pins her to the bed and threatens to murder her.
The Sisterhood or the Vigilantes have fallen into this territory at least once. The first seven books were all about the Vigilantes getting Revenge on the people who wronged them, and breaking the law in doing so. That's not supposed to be heroic. Despite this, once it got out what they were doing, they were considered heroes and household items. Reviewers at Amazon.com were quite happy to point out how the Vigilantes' behaviour went into this in the book Under the Radar. In that book, the heroes go to a cult of pedophile polygamists. The heroes acted rather abusively toward the adult women in the cult. In fact, the book spelled out quite clearly that the adult women didn't care about the treatment their own children suffered in the cult and deserved absolutely no sympathy. Reviewers, however, pointed out that the adult women were raised in this cult and brainwashed into believing in the cult all their lives, and that they are actually victims who you should feel sympathy for. With that said, the heroes have the adult women lined up and shave off the hair on their heads. They did this, because the cult leader likes long hair, and they wanted him to look at bald women to spite him. Reviewers pointed out what the Vigilantes did seems to be uncomfortably close to what the Nazis did in those concentration camps!
The book Sweet Revenge has this little gem from the thoughts of a stand-up male character named Bobby Harcourt. For such a supposedly stand-up guy, Bobby sounds like he hates people who aren't Americans like him, he sounds mean-spirited towards people from the Appalachians, and he apparently judges people based on their appearance and their given name before things like morals or personality.
He stopped at the receptionist's desk for his messages, hating how sleazy the young woman looked. He'd spoken to Rosemary about the receptionist's appearance and all she'd done was cluck her tongue and ask him if he wanted a lawsuit on his hands. It wasn't just the way the young woman looked, it was her stupid name as well. Sasha. No one named their kid Sasha except maybe a Russian mother. This Sasha was from Mud Creek, Mississippi. White trash, all ninety pounds of her. He rather suspected that Rosemary kept her on because Sasha made her look beautiful, which she was, but she was also a cold, relentless, heartless bitch of a woman. He'd found that out as soon as the honeymoon was over, much to his regret.
Gareth in The Rebel Prince. He is told he has to rape the protagonist in order to gain control of her psychic powers, needed to overthrow the evil leaders of the planet. He gets drunk to overcome his reluctance and does so, and feels bad about it afterwards. This is supposed to lead to him finding redemption. Instead, after claiming he is sorry, he continues to insist she is his wife (because they were married against her will) and uses mind control and threats of violence to control her. As well as using mind control to force her to learn pleasurable sex (it's still rape even if she enjoys it). The worst part is she winds up staying with him at the end because he "loves her".
Elizabeth Wakefield of the Sweet Valley High series is constantly presented as the "good" twin - smart, level-headed, kind, etc. But she frequently proves herself to be a hypocrite. She blasts her sister Jessica for being promiscuous while she herself repeatedly cheats on her boyfriends, she goes on and on about how people deserve a second chance, but apparently thinks this only applies to her friends, not Jessica's, and she instantly makes judgments about people without getting to know them, while again criticizing Jessica and her clique for doing the same thing.
Bertie of Théâtre Illuminata Trilogy. The reader is treated to her causing a bunch trouble around the theatre with no provocation whatsoever yet it's viewed as a matter of liberation and freedom. All of the noble and decent characters respect and admire her, or are at least willing to give her a second chance, while the ones who rightfully object to this behaviour, namely the stage manager, are just misguided bores for being upset that their livelihood is under fire by some bratty teenager. She's responsible for half of the bad things that occur in the book, yet she gets away with blaming everyone else. In fact, her immediate response to the stage manager calling her out on all the trouble she's caused? Attack him with a sword (injuring him and drawing blood, no less) and threatening to cut off his ear. She's rude and inconsiderate toward everyone yet somehow she's always in the right and remains the Golden Girl of the theatre.
Patrick Hennessy/Patricio Carrera in Carrera's Legions. An ex-military officer who uses his wife and children's murder as an excuse to gun down unarmed Muslim civilians (while they were celebrating a pseudo 9/11 attack, admittedly) and apparently take orgasmic pleasure in doing so, then establish a PMC that carries out extreme torture and ultimately nukes a city solely to kill the family of the terrorist ringleader who orchestrated the attack that killed his family. He also establishes a training regimen that gets hundreds of his recruits killed through things like faulty grenade training, use of poor-quality mortar ammunition, and extreme high-risk live-fire training that requires recruits to wear heavy vehicle-door-gunner armor, and responds to all of these deaths with sociopathic apathy. And since he's Tom Kratman's Author Avatar, Henessey/Carrera is repeatedly and at length described as the most incredible strategist and tactician in history, and every callous, sociopathic act of violence, negligence, and murder he engages is in is portrayed as saintly and righteous.
The prologue of the book opens up with a man going by the nickname of "the Blue Djinn" who takes pleasure in being considered outright evil, is portrayed with a savage, demonic light, orders the mass execution of hundreds of his enemies via crucifixion, and sells the wives and teenage daughters of said prisoners into sexual slavery. It isn't until you read further into the book that you realize that the Blue Djinn is Hennessy/Carrera.
In Fate of the Jedi, the New Jedi Order's complete and utter failure to use clearly available legal options to deal with Chief of State Natasi Daala is presented as a good thing. Instead of using the mounting public pressure on the legislature to remove her from power legally, something that had already worked to break the siege of the Jedi Temple and get the Court of Jedi Affairs dissolved, they mount a violent coup d'etat. This is the exact sort of thing Daala was trying to prevent, albeit misguidedly, with her increasingly draconian anti-Jedi policies, although it could be argued that the Jedi felt they needed to remove her from power as quickly as possible before she did even more damage, as public pressure wasn't having much of an effect on Daala at this point.
The Clave from The Mortal Instruments is an entire group of designated heroes. With their Fantastic Racism, inventive cruelty, and massive arrogance, it's a wonder how we're supposed to root for them in the final battle. In later books, the author runs with this, using them primarily as antagonists and focusing on their bigotry, controlling rules, schisms between different factions, and numerous other flaws that impact the protagonists.
Christian Grey of Fifty Shades of Grey is someone that we're supposed to sympathize with, despite him effectively raping the heroine on more than one occasion. After he meets Ana for the first time, he immediately orders a background check on her and receives her address, employment history, banking details, and social security number. He then proceeds to stalk her by showing up at her work, and later admits to tracking her cell phone. In chapter 21 of Fifty Shades Darker, Ana asks Christian about photos of Christian's previous subs, and he admits that he has them for the purpose of blackmailing his ex-subs into silence in case they should want to tell anyone that he likes BDSM. ("Exposure", in Grey's mind, always, always involves the news media and publicity.)
"This is going to sound cold, butthey're an insurance policy," he whispers steeling himself for my response.
The ONI characters of Halo's Kilo-Fivetrilogy. They're supposed to be painted as morally superior, especially compared to Dr. Halsey, who's portrayed as Mrs. Mengele for what she did in creating the Spartan-IIs. But their plan is to instigate a civil war among the Elites as a means to tip the scales in the UNSC's favor, essentially going behind humanity's only ally and weakening them. And in the long run all of their actions only cause more harm, as the rebel Elites will eventually become willing supporters of the Didact's mission to eliminate humanity.
Thankfully this is averted in all subsequent media, where it's made clear that ONI was simply foisting their own substantial share of the blame for the SPARTAN-II Program onto Halsey, especially considering that she began the program on their orders.
Leon from Pagan Lover frequently makes unwelcome advances on the heroine, kidnaps her on the day of her wedding (to someone she would have been Happily Married to no less), repeatedly threatens to rape her, and later forces her to marry him. Yet for some reason, he's the romantic lead, and women are supposed to consider him a better lover than the other guy.
The heroes of the Worlds of the Crystal Moon series, well, aren't. The male lead, for instance, is clearly intended to be a Genius BruiserScience Hero, but he acts more like an arrogant, selfish, sexist thug who bullies and belittles everyone he comes across, regardless of whether the situation actually calls for it, and doesn't think to share his advanced medical knowledge centuries ahead of the setting's time for the purposes of saving people's lives. Shalee, the female lead, gets off easier in the beginning by virtue of not really doing anything of her own accord, but loses the readers' sympathy once she starts using her time-stopping magic for the purposes of molesting people for absolutely no reason. George gets off more easily, since you're clearly supposed to think he's a scumbag.
Roald Dahl's Esio Trot from 1990 really suffers from this. Mr. Hoppy is treated as a sympathetic figure because he is a shy Stalker with a Crush, however he blatantly lies to Mrs. Silver about having the secret of getting her tortoise Alfie bigger. He then proceeds to kidnap Alfie and gradually replace him with bigger tortoises. Due to this Mrs. Silver ends up marrying him, never discovering that he lied to her. The 2015 BBC adaptation gives Mr. Hoppy Adaptational Heroism, and while he still marries Mrs. Silver in the end, he is also caught and called out for his actions.
Marcus Yallow from Little Brother. The book opens with him using his hacking skills to play hooky, including filling a Jerk Jock's phone with spam out of fear that he would tattle on him. He scapegoated his friend for stealing booze from his father to avoid getting in trouble. When his friends don't agree with his crusade, he disregards them. He often causes his own problems. He would have gotten out of his interrogation sooner if he complied with the Big Bad's orders to hand her his phone, despite knowing there was nothing on it that would have gotten him sent to prison. He then causes the DHS to up security after causing a security glitch just to make a point to his father.
In the Tortall Universe, Nawat from the short story bearing his name. After his wife Aly gives birth to human-looking triplets, he acts like they're 100% crows and must be treated accordingly, ignoring the team of highly experienced midwives in lieu of his second-hand experience of crow chicks. This leads him to pitch a fit when Aly tries to stick to human methods. When she gets mad at him for holding their babies out of a second-story window rather than use a diaper (something which almost causes a diplomatic incident when the Copper Isles really needs international help) she is painted to be the one in the wrong for not suggesting a compromise that he was clearly unwilling to listen to. This is all before he has to decide whether or not to follow crow law, which would involve him committing infanticide on his dwarf daughter—no, he doesn't consult Aly on this, even though Ochobu is her kid too. Oh, and he complains that Aly's Sight makes it hard to lie to her. Kind of hard to sympathize.
The protagonist from A Call To Arms in Alan Dean Foster's The Damned Trilogy. He's not a jerkass, and has humanity's best interests at heart. The problem? His idea of "humanity's best interests" involves sabotaging the Weave's efforts to get humankind to join them in the war against the Amplitur, a race who psychically, genetically and surgically Mind Rape every race they come across into enslavement to them, and who will at some point reach Earth. He wants humanity to become a peaceful race like all the other aliens, which is admirable. But his actions almost get humanity enslaved, results in millions of Human deaths when the Amplitur finally send a force to attack Earth preemptively, and ensures the war is prolonged for thousands of years. He is presented as a hero, when his actions make him the most evil person in the history of the galaxy.
Rhine is extremely rude and unsympathetic to Cecily, and generally seems pretty okay with the whole kidnapping and raping thing.
Gabriel is just generally bland, but we should not be feeling sympathy for Linden even a little bit. He honestly believed a row of dirty, crying, scared looking girls had chosen to be brides? And what did he think those gun shots were?
In The Game, Neil Strauss attempts to portray himself as the Only Sane Man who gets caught up in the world of pickup artistry and submits to it completely, before he eventually realizes that his pursuits are hollow and he ends up settling down with the right woman. However, his explanations come off as Jerkass-ish as best and completely reprehensible at worst. He steals women from their boyfriends in the middle of clubs, openly carries on relationships with multiple women at once, uses his job (as a journalist) to seduce celebrities who put their trust in him and generally acts passively when people call him out on his self-destructive behavior (to the point that Katja, the so-called Spanner in the Works, is more heroic and justified in her actions than he is). Even the ending of the book (Neil finally settling down with Lisa) is rendered hollow, as real-life accounts published after the fact indicated that he cheated on her and caused a breakup.
John Rumford from Victoria. First, we meet him when he is discharged from the US Marine Corps after interrupting a ceremony remembering their war dead, because he didn't feel it appropriate for a woman Marine to participate. After failing as a farmer he becomes, in effect, a professional rabble-rouser, with his group, the Christian Marines, paying him to plan strategies for preserving conservative Christian culture. Towards this end, he blackmails and kidnaps officials, and leads a militia against federal troops, holding their prisoners as hostages against further government intervention. After states begin seceding from the Union, he employs the same hostage tactics on a grand scale, lynchings, torture, forced relocations, biowarfare, and nukes Atlanta when black rioters seize the city. Blacks are welcome in his state, but only if they refrain from raising families in a city and accept a swift trial and hanging for any substantial offense, non-Christians are outright banished, and heretics burned at the stake. Among the various Straw Liberal successor states, the only one treated as a credible threat and worthy opponent are the actual Nazis, to whom he objects primarily because they are efficiency-crazed modernists. Oh yes, and Rumford becomes fond of 'Retroculture' and sets out to restrict any technology more advanced than was commonly used in the 1930s. In essence, it's a modern rewrite of The Turner Diaries as viewed by a Right-Wing Militia Fanatic.
D'Artagnon in The Three Musketeers is portrayed as a callow yet valorous young man out to prove his worth to the world and getting caught up in schemes of politics and love well over his head. And while some of his actions are certainly heroic, he tends to do some incredibly questionable and even villainous things. One of his first acts in the story is to attempt to murder a man who commented on his strange-looking horse. When he fails, d'Artagnon swears a vow to find him and slay him no matter how long it takes... over an innocuous comment about a horse. When his landlord (to whom d'Artagnon is in great debt) comes to him for help, d'Artagnon participates in getting him arrested for a crime he didn't commit so that he can live rent free and hit on the landlord's wife. d'Artgagnon declares his undying love for the landlord's wife, then pursues and eventually rapes Milady de Winter (by fraud rather than force, but still), then moves on and denounces her as a villain when she discovers his deceit and becomes furious. d'Artagnon's companions (the titular three musketeers) are little better, and the four of them only obey the laws convenient to them, lie to and intimidate whoever they please to squeeze money out of them, abuse their lackeys, and turn their noses up at anyone they deem lesser than them. Their two greatest accomplishments in the story are protecting the reputation of the lying and cheating Queen of France and tracking down and beheading a lying and cheating lowborn woman. (She was a complete sociopath, but the execution was not at all legal.) Despite this, they are portrayed as goodhearted men struggling to make ends meet and maintain their honor in a difficult world.
After spending so long in The Divine Comedy being extolled for her love, Beatrice spends her long-awaited introduction in Purgatorio coldly insulting Dante for missing his old mentor and openly admits that she wants to make him cry in sorrow for his mistakes after her death. The dissonance between expectation and reality is so strong that it is almost certainly an Intended Audience Reaction meant to show how unpleasant repentance can be. With more context from Paradiso, most readers come around to Beatrice.
Books of Kings: The Bible has plenty of supposedly heroic figures do questionable things, which sound terrible today due to Values Dissonance. But even so, King Jehu is among the most egregious cases. He starts out with killing the kings Joram of Israel (whose throne he then takes) and Achasia of Judah. Then he orders the courtiers to kill the elderly Queen Jezebel (Joram's mother), only to remain notably nonchalant about her gruesome death. Then he orders the death of all of Joram's younger brothers (out of whom some must have only been children), everybody with any connection to the former royal house, some relatives of Achasia, who had not done anything except for saying that they came to see the now extinct former royal family, and all the remaining Baal prophets, who had even been tricked by Jehu into coming to a party where they were killed off. Jehu is never seen doing anything but having people (out of whom most are never seen doing anything wrong) killed, and his body count seems to end up being much larger than that of Queen Jezebel. But he was able to defeat the supposed bad guys and was supposedly chosen by God, and God appears to approve of his actions. So he must be a hero, right? And to really make us see that worshipping an idol is worse than killing hundreds of supposedly "evil" people (most of whom clearly were defenseless aginst his attacks), the narrator seems to only have one criticism about King Jehu: He stayed on as king of Israel for twenty-eight years. But he still never got around to removing the golden calves, which were a part of a local idol cult. Because a few statues were obviously more abominable than all that needless bloodshed, that Jehu did during his violent coup d'etat...
This gets discussed in Glory Road after E.C. "Oscar" Gordan agrees to meet with a boy who wants to touch the hero's sword. Oscar gives him a quarter and tells him how the face on the one side is the father of his country and the bird on the other side is a majestic creature that represents freedom and courage, and even gives the boy a new middle name to bear with honor when the kid grows up to become a hero himself. After the boy leaves Oscar's companion Star absolutely gushes with adoration. "Noblesse Oblige can only be felt by those who are in fact noble. I have known many heroes who would have been fed in the kitchen, if their deeds did not merit them a place of honor at the main table. But you..."
Adam by Ariel Schrag has the titular character. He is a cis heterosexual male who is mistaken for a transman because he's a minor that managed to sneak into gay clubs. When he meets a lesbian named Gillian, he decides to use this misunderstanding to his advantage so that he could sleep with her, and he succeeds, which falls under Rape by Deception. Adding to the creepiness is that he's 17 while Gillian is over 18, so he also tricked an adult into committing statutory rape. Not only does he get away with it, he and Gillian get together even after he was exposed.
Discussed in-universe in Meagan Spooner's Hunted. Yeva tells the tale of "Tsarevitch Ivan, the Fire Bird and the Gray Wolf" to the Beast and says that while the tale is supposed to have a happy ending, she doesn't see it as one because Ivan was extremely greedy and careless (constantly disobeying the wiser wolf's warnings to not take more than he came for) and was never punished for it. The Beast, who initially refused Yeva's suggestion that she call him Ivan because he's not a hero, changes his mind after hearing her opinion on Ivan and says that she can call him Ivan because Ivan wasn't really a hero. Not only that, but it turns out that the Beast actually was Prince Ivan centuries ago — or at least the prince that inspired the tale — and most definitely did not get off scot-free for his greediness and carelessness.
The Canterbury Tales has a lot of this, sometimes due to Values Dissonance and sometimes due to Stylistic Suck—where one begins and the other ends is one of the biggest topics of debate, as the story's framing device provides a lot of ambiguity. As a good case example, the Knight's Tale has Palamon and Arcite, who nearly beat each other to death in the woods in the name of fighting over a woman neither of them have met in person and who doesn't actually like either of them when they do meet.
In Shades of Magic, stealing is the least of Delilah Bard's crimes. Over the course of the first two books, she steals anything she can get her hands on despite having been offered honest work, holds a dangerous artifact hostage to force Kell to take her out of her own dimension because she wants an adventure, cheats her way into a tournament by first seriously injuring and then wrongfully imprisoning someone with whom she had no personal quarrel and who'd actually gotten in on merit, murders several people in cold blood for having caught her cheating, and repeatedly abuses magic she barely understands without any regard for the potential consequences to herself or others. She never suffers any consequences beyond an occasional light scolding for actions that are severely punished when committed by any other character, and is consistently treated as a hero throughout.
The protagonist of the fairy tale The Tinder Box murders the witch when she refuses to tell him the tinder box's special properties, secretly courts (and in some versions of the story abducts) the princess repeatedly, and — after getting arrested and sentenced to death for this — kills the kingdom's ruling members, including the princess' parents, before taking over and marrying her. His hero status is questionable at best. This was likely deliberate; the author, Hans Christian Anderson, often wrote stories that deconstructed tropes, one of the most blatant being "The Snowdrop."
A deliberate in-universe example is Pon the gardener-boy in The Scarecrow of Oz. He's the "romantic hero" of the story who somehow won the heart of Princess Gloria, but the other characters comment on what a useless drip he actually is, including Gloria herself, and he does nothing to contribute to the eventual defeat of the villains.
Linden Rathan of Joanne Bertin's The Last Dragonlord and Dragon And Phoenix is repeatedly stated to be easygoing and "not an ass", but this is only evident when everything's going his way, and he's fussy and whiny in response to even minor problems. As soon as he's actually balked It's All About Me goes into full effect and he evinces a towering, poorly-managed temper which he takes out on servants. A near-immortal, he's gone six hundred years waiting for his soultwin but this has not taught him patience; when he finally finds her, one of his fellow Dragonlords says he needs to take it slow for her safety and he tries to strangle the man. Only said soultwin and children are not targets for his rage, but he's deeply possessive of this woman and controlling, and screams at his friends and breaks things when they suggest she has to do plot things without him. Characters who know him frequently remark that this isn't like him, but he's so often portrayed as a throbbing nerve it's hard to believe them.
Zoey, the main protagonist of The House of Night, comes across as an awful person, constantly belittling other people in her narration, slut-shaming other women, and being extremely hypocritical (e.g. she derides other girls for 'acting like sluts' while cheating on her own boyfriend with at least two other men)). She has a habit of judging people as good or bad based more on how she personally feels about them as opposed to their actual actions; for example, she views her former best friend as an asshole simply for dating her ex-boyfriend (when Zoey already had a new beau), while she is happy to overlook Kalona being a Serial Rapist and thinks he's a good person deep down simply because he loved her in a past life and she still finds him attractive. She also tends to be a rather passive heroine, who achieves her goals or gains new skills thanks to divine intervention from Nyx more so than her own efforts.