: How to make good anti-heroes? Dr.House, the God-Emperor of Mankind, Han Solo, and so on, and so forth. Something is appealing about anti-heroes, for instance: Superman is bland, perfect and ultimately

The BEST villains are HEROES in their own story.

From their perspective they are doing the right things!

Voldermort is a terribly flat villain. His goal is to be an immortal evil man... BORING!

Start wars Emperor ... oh look at me.. I want to be emperor of the galaxy. I want to kill the Jedis. I have a red light saber, I talk in a creepy voice, and I have an ominous theme music,.... BORING!

Heath Ledger Joker... a villain without the need to justify himself... just an agent of chaos .. quite interesting.

Tywin Lannister... why is it more evil to murder hundreds at a wedding, than killing tens of thousands on a field of battle? He is a great antagonist, because, he TOTALLY DOESN'T see himself as a villain at all. In his mind, he is defending the realm, promoting his house, and preserving his name.

The laziest villains are those who prance about saying look at how evil I am.. like Ramsey Bolton. Boring...

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Anti-hero is the one who does the right thing, despite being a not very good person. Someone with moral flaws, weaknesses, ambiguity, but eventually capable to do right.

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Some definitions: Since we're talking archetypes, I have no scruples basing the following discussion on the concept of the Hero's Journey. (See Chris Vogler's discussion for my favourite interpretation.) Definitions and etymologies are taken from the englisch wiktionary. I add this answer since I have the feeling that people use the term "anti-hero" in various ways. This post is meant to clarify what an anti-hero actually is.

The protagonist: from Greek, "first actor". The character that drives the story forward.
The hero: Several etymologies -- from Old French over Latin to Greek and an old prototypical Indo-European language, "protect, serve". In Greek drama, a hero is a character that serves others. S/he's altruistic and values the communal good higher than his or her own. S/he's willing to sacrifice him- or herself for others. In other, more narrow senses, a Greek hero is character that participated in the Trojan war, or a god or demi-god that was revered in his or her own shrine.
The antagonist: From Latin and Greek, "anti" (Greek, "against") and "actor". An antagonist preserves the Status Quo by keeping the protagonist from driving the story forward. Unlike the anti-hero, the antagonist has a well-defined goal, that, however, is opposite to or in other conflict with the hero's goal. The protagonist must deal with the antagonist, if the story is not to stagnate. Chris Vogler draw the following comparison: The hero and the antagonist are forces that want to drive the story into different directions. Think of them as horses that try to carry a cart into opposite directions.
The villain: From Old Latin, a serf or peasant, someone who is bound to the soil of a "villa", the antique equivalent of a plantation. Interestingly, the original meaning of this word has very little(*) to do with today's meaning. Returning to Chris Vogler's simile of antagonist and protagonist as characters that pull the story into different directions, the hero and villain represent the different possible solutions of the story. They are trains heading towards each other. The villain has the potential to destroy the hero. -- In terms of basic archetypes, the villain is the manifestation of the hero's shadow -- any character trait that can potentially destroy the hero and must be dealt with. The whole purpose of telling the hero's story usually is to show how the hero faces his shadow and integrates it into his or her personality. This psychological dimension of the struggle between the hero and the shadow can be more or less obvious in a story, but in the end, the hero "defeats" the shadow. The shadow is no longer able to destroy the hero. (I make a distinction between the shadow and the villain here, since the shadow does not always need to manifest as separate character.)
The anti-hero: "anti" plus "hero". The defining feature of a hero is that s/he acts to protect others. In the simplest possible definition, the anti-hero hence doesn't. This does not necessarily mean, that the anti-hero is selfish or that s/he actively strives to harm others; it simply implies that the anti-hero is not heroic. Maybe this is because s/he's not part of a community; maybe s/he doesn't have the means; maybe s/he's not aware that help is required. Any reason that keeps a character from acting in an heroic way turns him or her into an anti-hero.

An interpretation

In the framework of the Hero's Journey, the protagonist usually evolves into a hero. The protagonist sets out with a well-defined goal, undergoes a transformation, and returns in the role of the hero. His or her personality has changed, usually for the better.

The key feature of a hero, in my opinion, is that s/he recognizes the need for change and actively tries to establish this change.

The negation of this concept is a character that refuses to change or participate in it. This definition encompasses the narrower definition above, of an anti-hero as a characters that does not protect others: If s/he is not willing to face the challenge that s/he's presented with, s/he does not have the opportunity to evolve into a hero.

Characters differentiate into heroes and anti-heros when they decide whether they take on the challenge at the core of the story or not. In terms of the Hero's Journey, this challenge is presented in the form of the "Call for Adventure". While both the hero and the anti-hero may engage in a "Refusal of the Call" -- a clever hero will know that heeding the call is dangerous and will be reluctant to actually follow it --, only the hero will finally "Cross the Threshold" and accept the challenge. The anti-hero, on the other hand, walks away from the challenge.

This principle is variable, of course. Some heroes are passive throughout the first half of their story; to cross the threshold was not their explicit decision, but rather, they didn't have a choice. In the end of the story, however they have faced the challenge and mastered it. They have grown. At the same time, the anti-hero still idles away in his or her old position and hasn't changed a bit. In a sense, a piece of narration that tells of an anti-hero is an "anti-story" -- since, really, nothing happens. (Of course an interesting story could be about a character that refuses to change while his entire world turns upside-down. That would be a valid, and possibly very effective, story that however revolves around an anti-hero.)

Now, with this definition in mind, what can we conclude about the characters you list as examples of anti-heros? Unfortunately, I only know Tony Stark well enough to discuss him, but with Tony, it's really quite simple: Tony emerges as a hero. Yes, he is flawed and peculiar (this is what makes him interesting and relatable) -- but at the end of day, he has, undoubtedly, evolved into a hero. He has heeded the call to protect people he cares for and is willing to sacrifice himself. He's a storybook hero, really.

A discussion

An important thing to keep in mind when developing characters along the lines of an archetype is that characters can switch roles throughout the story. A passive hero might appear to be an anti-hero for a while. A trickster might turn out to be a villain. A shapeshifter is changing constantly, anyways, and a hero -- i.e. a character that already completed the Hero's Journey, which is usually not the protagonist -- might turn into a mentor or even into a villain at a later point of a story.

Overall, the goal of the Hero's Journey is to transform a character into a hero. That explicitly means that the protagonist, at the beginning of the story, is not a hero yet. By the end of the story, however, s/he will be.

Since stories are generally about change, investing too heavily into an anti-hero in the sense outlined above is usually not a smart move. Your audience generally is not interested in a story in which nothing changes. Anti-heros have their place in literature and popular culture, but I would argue that you should only engage with them if you have a very good reason to do so.

Conclusion: How to write a good anti-hero?

People do not generally root for an archetype and condemn another. We can cheer for the villain of one story and the antagonist of the next, and sometimes be horribly bored by the hero. (Think Pirates of the Caribbean. Will is the hero, but everybody loves Jack, who's not changing and who's certainly not promoting the greater good. Stil, his wit and charm appeal to the audience more than Will's blunt "goodness" of the first movie.) Whether we like a character or not does not depend on the archetype s/he refers to, but on whether or not the character resonates with us. In that sense, the question is not how to write a good anti-hero, but how to write a good character in general. (Although what "good" means in that sense is open to interpretation. For me, the qualities "interesting", "realistic", and "complex", are much more important than the generic "good" in the sense of "kind" or "heroic".)

And here's the quintessence: People are different. I don't believe there's a single good way to write a universally appealing anti-hero or character in general.

A good way to start is to analyze the qualities that appeal to you(**), personally, when developing a new character. What do you like? What can you root for? Chances are, if you condense these qualities and pour them into a well-rounded characters, other will root for this character as well.

(*) A wild association. The hero is the character that successfully changes in a story. The villain, always a potential hero in his or her own right, fails. In this sense, the villain is "bound" to his or her Status Quo. S/he's unable to accomplish the transformation that is mandatory for a hero. Not unlike a serf that is bound to a specific patch of soil, the villain is unable to journey as the hero does and fails to change his or her world. Interestingly, this always makes the villain an anti-hero, but not all anti-heros are villains.

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One writer's opinion:

Heroes:

Begin here: They engage in altruistic risk and sometimes sacrifice; and the audience sees that. Many Germans that hid Jews from the Nazis did not get caught, so they lost nothing, and in material terms sacrificed nothing. Well, peace of mind, personal terror, etc, perhaps food and fuel and space in the root cellar, but they lost nothing of major consequence.

Nevertheless they were heroes, they saved the lives of others. A man that dives off a 30 foot high bridge into a raging river to save a child he spotted (really happened, saved the kid) risks ending his own life for a child he never met. He didn't lose his life. He may have lost his iPhone and ruined a good pair of shoes, but those are minor material sacrifices that vanish in the light of how much altruistic risk was taken. One might nitpick that getting famous is a self-interest reward, but in this case there wasn't even a thought of fame; bystanders saw a man watching the flooding river, that suddenly vaulted the rail and dove in: Nobody else saw the kid; so had he failed, it would have just been an apparent suicide.)

There is a borderline case worthy of its own debate: Does doing something altruistically nice make somebody a hero? If Superman raises a hand to stop a [standard lead] bullet that would have struck a man in the head: Is he a hero for expending the energy, even though he personally risked absolutely nothing in the process?

I think most people reflexively think "Yes," but I tend to think "No." I like to be careful with words; and to me this is an act of kindness, not an act of heroism. The same goes for giving a homeless person five dollars: No personal risk is involved.

That said, such altruistic acts are important in the development of the hero, because they demonstrate altruism is an inherent part of their nature; an inclination toward expending time and effort to help others is obviously a prerequisite to adding personal risk and turning that altruism into heroism.

Thus in writing, for plausibility, it is best to establish first that the character will indeed expend time and effort to help other people, even if that is just steadying them after a slip or pointing out they dropped their wallet. So later, when risk is added, they do not seem out of character for doing something altruistic.

On to Anti-Hero:

In much early fiction, heroes are relentlessly altruistic to the point of boredom, or what becomes boring wish fulfillment fiction like (again, IMO) Superman.

Introducing flaws and actual criminal behavior into a character that will BE a hero makes them interesting and puzzling. A better Superman, for example, is Hancock (played by Will Smith); in the opening scene he looks like a crusty homeless man sleeping off a drunk on a city bench, being irritated by a kid. But one sees very quickly that Hancock is an irritated and disdainful superman that does fight crime and save people, with zero regard for property or infrastructure or the cost of repairing it, and with zero skill in personal relationships, politics, or public relations. He's an asshole; but he saves people's lives.

Then when risk to himself does develop, he keeps going; and this is no longer just kindness, it becomes heroism.

The key to the anti-hero is balancing their bad side with enough personal altruistic risk to compensate several times over. Otherwise, you just have a villain, or an incoherent character.

Or your anti-hero may be an anti-villain: Somebody clearly causing more harm than good in the world, but the audience can also sympathize and understand why. For example, a man using actual missiles to blow up crowded public areas, like restaurants or stores, to kill mobsters he knows are in there: regardless of the collateral damage in deaths of innocents. His argument is that the collateral damage is far less than what he knows the future damage would be, so society is ahead whether they know it or not, the mourning and losses of today would be tenfold as much if he hadn't punched the button.

But that is not a hero, despite the risk he takes (the mobsters are full tilt in trying to kill him), despite his truly altruistic motives, because it is not clear that this character is actually saving anybody (the writer makes it clear this is true in the character's mind; but it will never be clear to the audience unless it is a time-travel flick where the alternative future with the mobster alive is made certain).

Anti-Heroes must voluntarily take enough altruistic risk to be heroes. It will help in your writing to demonstrate to the audience that this risk is very real; they can be hurt, injured, and suffer losses for taking such risks, they could really be killed or destroyed.

Then just be aware that the more of an insufferable asshole you make them (always fun), the bigger their ultimate risk and sacrifices must be to outweigh that.

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What makes anti-heroes interesting characters to read about?

To find that out, let's compare the morally flawed anti-hero with the cliché of the perfectly virtuous hero.

They do things the audience wouldn't dare to do. Be mean to people who annoy you. Disrespect authority figures. Indulge in guilty pleasures like casual sex and recreational drugs. Give bad people the punishment they deserve. Ignore the traffic rules. These are things many people in your audience would like to do, but can't because they are nice and civilized people and society tells them it's wrong to do these things. Living out these fantasies through a sympathetic viewpoint character can be an enjoyable experience.
They are in danger of moral failure. Offer Hero an immoral temptation, and he will laugh at you. It would be a gross violation of his moral code, so he won't be tempted for a second. The audience knows it, so this situation isn't exciting at all. Offer Anti-Hero a temptation, and she might seriously consider taking it. She will have an actual internal conflict and the audience can't be sure how she will resolve it.
They have to live with the immoral decisions they make. The hero doesn't take moral missteps, so she can sleep at night. The only thing she can possibly be held accountable for is not being competent enough. But such critique can be easily dismissed as unreasonable, because after all she was doing as best as she could, and you really can't demand more of her. But because Anti-Hero is allowed to make morally wrong decisions, he also has to experience the consequences. He has to face the people he wronged. His critics can not be dismissed that easily, because they have a point. And even worse, the anti-hero has to face his own conscience.
They have more room for character development. The hero is already a perfectly virtuous person. There is nothing he could learn or experience which would make him even better. Not so the anti-hero. Over the course of the story, she can overcome her vices and learn to be a better person.

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The underlying quality of a good anti-hero is that he (or she) genuinely believes himself to be doing his best in the circumstances he lives in -- despite an outsider (the reader) being able to see his flaws. In each case, as well, the anti-hero is in fact very, very good within his range of expertise.

Han Solo is incapable of strong attachment (to other humans -- doesn't have a problem with Chewie and the Millennium Falcon) and a deeply rooted cynic, but is a galaxy-class pilot with a very capable ship. Gregory House, M.D. is a drug addicted misanthropist, borderline narcissist, and general asshole, but one of the most brilliant diagnosticians alive (I'm much less familiar with the God Emperor). Tony Stark (at least in the movies) is obsessed with the harm that was done in his name before he found out how his inventions were actually being marketed, and he can invent things no one else can (see the exchange between Stane and the lab head about the miniature arc reactor) -- and seems to have complete disregard for his own safety, once "activated".

In each of these cases, the character, internally, believes himself to be doing what he has to do, to have little or no choice in the "bad" things. House justifies much of his misanthropy with the "Everybody lies" tenet; Solo thinks that because he's always in debt and people are trying to collect from him, he has to do the things he does. Stark freely admits to the "laundry list of character defects".

On example of an "evil" anti-hero might be Punisher. He's obsessed with revenge, but has no desire to hurt anyone other than his targets -- and with his skills, is likely to avoid collateral damage. Further, his targets are bad guys, which makes him an anti-hero, doing a form of good for society even as he does things we'd normally consider evil.

Write a character like that, and do it well, and you'll have a "good" anti-hero.

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