No More Mr. Nice Guys: How to Write Flawed Characters & Antiheroes

Flawed characters and antiheroes make for fascinating protagonists—but their behavior can risk alienating readers. Follow this blueprint for flawed-yet-relatable heroes who can still provoke empathy.

Not so long ago it seemed every writer agreed: Protagonists must be “likable.”

Then something curious happened. Everyone began to realize that “likable” is merely a few degrees from “nice,” which in turn nudges perilously close to “boring.” People may not like spending 200–500 pages with a wanton wretch, but they don’t like wasting time with a Boy Scout’s shadow, either.

In truth, protagonists need to be compelling—better yet, fascinating—not necessarily agreeable. And what makes characters compelling or fascinating is their capacity to surprise. A character who is predictably anything quickly becomes a one-trick pony, incapable of maintaining reader interest for long.

The challenge is especially daunting for characters who may disaffect readers with some particularly repellant trait—a vicious temper, a drinking problem, arrogant self-confidence, outright immorality or even criminality. And yet some flawed characters are among the most fascinating—and profoundly loved—protagonists of all time. To name just four:

• Holden Caulfield, The Catcher in the Rye (an aimless, jaded, venomous cynic)

• John Yossarian, Catch-22 (a World War II bombardier who will do anything to avoidflying combat missions)

• Dexter Morgan, the Dexter novels (the serial-killer son of a serial killer)

• Rachel Watson, The Girl on the Train (a mysteriously obsessed drunk)

How, then, does one create such a potentially reprehensible character who nonetheless fascinates?

The Allure of Transgression

We may tell ourselves that we respect the law and those who uphold it, but there’s a little larceny in every heart. The character with a wily knack for seizing a dubious opportunity (or avoiding an odious chore) seldom fails to appeal—as long as no one gets hurt. This points to:

Two Important Truths

1. There’s an implicit understanding that we had no part in making the rules, and that many of them are meant not to protect us but to keep us in line. Our intrinsic desire for freedom and autonomy rankles at this sort of benign coercion, and we instinctively recognize that the goal of “the law” is often not just order but conformity, even oppression. The suspicion that there is “rot at the top” and that corruption is the rule, not the exception, never lurks far beneath the surface. And so, with that in mind, we admire those who refuse to fall into line.

2. There is a natural limit to the appeal of transgression: the degree of harm to others. We don’t mind seeing a greedy plutocrat bilked or a bully brought down a peg, but empathy wanes in direct proportion to the innocence of the victim. Push this too far, and you’ll need to provide a countering virtue that shows us the character isn’t simply a monster.

The Power of Contradiction

That last point can be generalized: We can accept a great deal of unpleasantness in a character as long as we see it balanced against something that inspires empathy or intrigues us.

Charles Portis in True Grit employs such contradictions masterfully. Despite Mattie’s youth she is indomitable and savvy in business. LaBoeuf is courageous despite a foppish concern for appearance. Cogburn, the one-eyed drunken fat man, is relentless, cunning and, in the end, valiant.

These kinds of incongruities automatically intrigue—and offer the prospect of surprise. We can’t help but wonder at what sort of psychological glue holds these supposedly opposite traits together.

This is especially true of transgressive characters. Absent some redemptive quality, they risk alienating readers. To create compelling contradictions, explore the following:

1. Contradictions based on contrasting influences. It’s a basic fact of life that we must be “many things to many people.” Our behavior at the office risks serious consequences if it veers too close to our behavior at home—or the local bar. Explore what incompatible environments your character must navigate and the behavior they exhibit in each. Alternatively, look to the persons who demand or inspire opposing inclinations. Let them be the devil on one shoulder and the angel on the other at every decision point in the story.

2. Contradictions based on competing morals or goals. Don’t neglect to explore your character’s moral code. In doing so, however, avoid trying to make it too neat and tidy. Explore ways in which he holds opposing views of the same thing—e.g., they may consider innocence in one character nothing but stupidity or naiveté, yet see it as a kind of gentle nobility in another. Or he may believe in both righteous vengeance and forgiveness, and struggle to know when to apply one or the other.

3. Contradictions that result from a secret or deceit. Secrets automatically add depth to a character by creating an inner and outer life, what is revealed versus what is hidden. By making the character act in a way that conceals his secret, you create tension. One great example: Maxim de Winter in Daphne du Maurier’s Rebecca. His secret, that he did not love his late wife but hated her to the point of murder, creates the mysterious fits of temper and distance that Rebecca (and the reader) find not just off-putting but repellant. Yet he’s the heroine’s courtly love interest—how can that be?

Contradiction also alerts the reader that there is more than one side to the character, and thus implicitly suggests that he can change. Readers will extend considerable patience to an otherwise dreadful character if he also possesses the wherewithal to reflect, learn from failure or otherwise turn in a new, more agreeable direction.

The Contradictory Exemplar: The Antihero

The character type referred to as the “antihero” justifies an entire article on its own—I know, because I’ve written one. But for our purposes, the key trait to recognize is what distinguishes an antihero from a protagonist who merely suffers from distinct moral flaws.

The flawed hero is potentially capable, through insight, of recognizing his moral limitation, seeing the damage it does to himself and others, and rectifying his behavior. In fact, this sort of transformational arc lies at the heart of many stories featuring such a character.

In contrast, the antihero stands at the center of an irresolvable moral conflict. Think of him as having a devil on one shoulder, an angel on the other, and neither ever convincingly gains the upper hand.

Homer’s Odysseus is just such a character—while capable of heroism and daring, he also exhibits treachery, deceit and cowardice. It’s precisely that dual nature that keys our fascination.

In the 16th century, the picaresque novel emerged in Habsburg, Spain, epitomized by The Life of Lazarillo de Tormes and His Fortunes and Adversities. Instead of the steadfast knights of the chivalric romance, these novels featured lovable, wandering rogues and thieves, known as picaros, and the stories recounted their morally questionable but never explicitly wicked exploits. The appeal of the picaresque novel spread across Europe and took solid root in England, where its popularity survived into the 19th century in novels featuring rakish heroes such as Tom Jones, Moll Flanders, Barry Lyndon and Martin Chuzzlewit.

Lord Byron provided another variation on the type, encapsulated in these lines concerning the pirate hero of his verse tale The Corsair:

He knew himself a villain—but he deem’dThe rest no better than the thing he seem’d;And scorn’d the best as hypocrites

This returns us to the theme of justifiable transgression. When a society’s cherished ideals are exposed as serving only the corrupt few, the antihero typically emerges as an antidote to the prevailing hypocrisy. In being neither evil nor virtuous, but revealing instead an uneasy marriage of both tendencies, he seems more genuine and convincing than the more pious and predictable characters the powers-that-be prefer.

Indeed, the recent resurgence in popularity of antiheroes in long-format TV—embodied in such characters as Tony Soprano, Jimmy McNulty, Patty Hewes, Don Draper, Nancy Botwin, Ray Donovan and Walter “Heisenberg” White—reveals not just a need for characters of sufficient moral and psychological complexity to drive a multiseason series, but a newfound awareness that many old American verities (e.g., equal opportunity, fairness, decency) have worn thin, revealing the naked aggression, vanity and greed underneath.

Creating Empathy Through Desire, Struggle and Vulnerability

Through some odd magic of the human heart we almost always feel for those struggling in pursuit of a meaningful goal—even if it’s a bank heist.

In Catch-22, John Yossarian’s determined efforts to escape combat create in the reader a rooting interest, if only because he so doggedly pursues his desire “to live forever or die trying.”

In The Girl on The Train, readers initially put off by Rachel Watson’s drunken ruminations as she rides the train are soon reeled back in by what is clearly a profound desire to recapture, however futilely, the life and love she lost.

To desire something that requires struggle automatically makes us vulnerable due to the risk that we may fail. That risk may take one or more of several forms:

1. Existential (risk of physical harm)

2. Emotional (loss of hope, joy, meaning, etc.)

3. Relational (risk of loss/disconnection with someone)

4. Moral (risk of judgment)

When using struggle and desire to create empathy for an otherwise offensive character, don’t neglect to explore just what risks the character faces. The more those risks are emotional, relational or moral, the better your chances of deepening the empathetic bond.

Finally, another tried-and-true way to create empathy for even a loathsome character is to give him “a kid ora dog”—i.e., give him someone to care about other than himself. We care about those who care about others.

You can also turn this around. We typically empathize with a character if another, more personable character does so too.

Three Essential Traits

Above and beyond the empathy factor, three key traits can help mitigate the portrayal of an otherwise harsh, off-putting or outright despicable character.

1. Humor: It’s amazing how much obnoxious behavior we will put up with from a character who makes us laugh.

2. A lust for life: A love of food, music, art, travel or any other aspect of an attractive life can reassure us that an otherwise objectionable character is not a rancorous misanthrope stewing in his own bile—or worse.

3. The intimacy of insight: We tend to judge less harshly characters who look at themselves and their behavior clearly, honestly and in-depth. Even a psychopath like Dexter Morgan becomes a bit less terrifying because we’re invited into his thought processes, which are elaborate, detailed and fascinating.

The importance of insight, especially, cannot be underestimated. Even if a character possesses a compelling contradiction that suggests he’s capable of change, absent insight, it’s doubtful he can or will make the effort. A character can’t turn in a direction he can’t see.

Even if the character doesn’t change, the fact that we are invited inside his mind creates an intimacy that is hard to resist. Whether his thoughts are externalized directly to the reader or audience (Richard III, Frank Underwood in “House of Cards”), provided in first person (Freddie Clegg in The Collector, Lou Ford in The Killer Inside Me) or in close third (Tom in The Talented Mr. Ripley), that intimacy creates an implicit, irresistible bond with the reader. It’s hard to say no when we’re so graciously invited inside.

Bad vs. Worse

We can often accept a certain amount of wickedness in a protagonist if he’s pitted against someone genuinely, remorselessly evil.

The entire heist genre is predicated on the fact that the protagonists are clever professionals working to score against a vastly more powerful and largely amoral (if not immoral) person or entity—another criminal, a bank, an insurance company. This comes with a caveat: the crime involves money, not mayhem.

One of the great innovations of the Dexter series was that it violated this unwritten rule, but did so in an acceptable way. Yes, Dexter’s a serial killer, but he only kills other murderers.

This same ethical setup is the premise of a form of moral argument known as pathos, in which an everyman employs immoral means to pursue something he considers invaluable in the face of an overwhelmingly powerful person or system. Even though we know the

protagonist is doomed to fail, we root for him because we identify with the little guy swinging for the fences, and we all understand that the world isn’t fair.

This form of moral argument animates not just the crime genre known as noir, but a great many plays, films and novels written in the shadow of the Great Depression and World War II, from The Postman Always Rings Twice to Death of a Salesman. A resurgence followed in the late 1960s and early 1970s with such films as The King of Marvin Gardens, Dog Day Afternoon and Chinatown, and again in the mid-1990s and early 2000s with novels such as Mystic River.

Turning Virtue Into Vice

Often characters who offend readers merely push a virtue to an unacceptable extreme, but the fact that it’s a virtue that lies at the heart of the problem suggests that it can be corrected if the character has the necessary insight.

Examples of ways virtues can be pushed to an objectionable extreme:

• His loyalty obliges him to overlook the immoral acts of others

• His courage or ambition leads to recklessness

• His commitment to honesty makes him hurtful

• His love of action turns into an addiction to the adrenaline rush

• His concern for order leads to a rigid, even heartless obsession with rules

• He is so certain of his moral rectitude he’s blind to his own bad act.

The key to a great protagonist is how compelling he is—not how nice. Employing the techniques discussed above, alone or in concert, can help turn even an abhorrent character into one your readers will want to stick with to the end.