Anti-Hero or A**hole: The Fine Line Between Flawed and Frustrating

The Art of the Anti-Hero: Why We Root for the Worst People

Now that I’m back to reading submissions, I’m finding plenty to talk about in my articles—unfortunately, it’s mostly of the “don’t do this” variety.

I’ve lost count of how many stories feature characters so insufferable that I wouldn’t want to spend five minutes with them, let alone an entire book. They aren’t morally complex or compellingly flawed; they’re just awful—rude, selfish, cruel and/or self-entitled.

The writers were clearly aiming for an anti-hero—think Walter White, Don Draper, or Tony Soprano—complicated, layered, and fascinating. Unfortunately, they created flat, annoying and irritating.

To be clear, I’m not just talking about dramatic genres. I’ve read many a YA “mean girl” that has me hoping she’ll have an industrial accident to end my pain. I considered giving these bad boys, some female companionship—Regina George of Mean Girls or Kathryn Merteuil from Cruel Intentions—but felt their characters were too much of a deviation from the point I want to make here. So, we’ll save them for another time.

Let’s look at what makes an anti-hero work, and what cause them to fail. There’s a test at the end to see how your character(s) hold up.

Why We Root for the Rule Breakers

Some of the most compelling characters in literature and television aren't heroes at all—they're deeply flawed, morally compromised, and often outright criminals. We don't root for them because they're bad; we root for them because they're complex, and, in their own way, deeply human.

A well-written, morally challenged character doesn’t just shock us with their deviant actions; they challenge our sense of morality, force us to question our own boundaries, and sometimes even make us admit we might make similar choices in their position. We don’t always like what they do, but we understand it.

Show, Don't Explain

One of the most common errors I see is the “flashback justification”—where the writer shows us the protagonist doing or saying awful things, then hits pause on the story to show us a childhood filled with neglect, abuse, or other trauma. See, they're not just a jerk—life made them this way!

Flashing back to a tragic past doesn't automatically make a character compelling or excuse bad behavior. The trick is to know how to craft their complexity in the course of the present story.

If you're writing a protagonist with a dark past, don't use it as a crutch to make them sympathetic. Their past needs to inform their present in ways the reader can experience. Let the backstory trickle in through dialogue, reactions, or decisions, rather than spoon-feed exposition.

Let's use Walter, Tony, and Don as an example. They captivate us because the pain of their past is steeped into every action they take in the present. The reader (or viewer) gets to piece together why the character is the way they are, making the characters’ struggles more relatable and impactful.

Walter White (Breaking Bad)

💡 Backstory: A brilliant chemist who was never recognized for his abilities. Now a high school teacher, diagnosed with cancer, turns to making meth to provide for his family.

❌ Avoid: Lengthy exposition about his scientific brilliance and unrealized potential, making us pity him for ending up as "just a teacher."

✅ How the Show Did It: We see his anger when his former colleagues—now billionaires from his research—offer him financial help. We see his need to prove himself and finally have agency. The past isn’t just explained —it drives his every decision.

Tony Soprano (The Sopranos)

💡 Backstory: Grew up with an abusive mother and a mobster father, shaping his anxieties and violent tendencies.

❌ Avoid: Overemphasizing childhood scenes that explicitly connect every adult behavior to a specific childhood trauma.

✅ How the Show Did It: Tony's complexity emerges through his contradictions—his capacity for brutal violence contrasted with panic attacks and vulnerability in therapy. His present is shaped by his past, but never as an excuse.

Don Draper (Mad Men)

💡 Backstory: Grew up poor, raised in a brothel, stole a dead soldier's identity to escape his life.

❌ Avoid: Relying on his traumatic past to excuse his constant infidelity and emotional unavailability.

✅ How the Show Did It: Don's past emerges organically through his behavior— his inability to sustain authentic relationships. His advertising genius stems directly from his talent for reinvention and understanding of desire.

Unlikeable ≠ Compelling

Being morally gray does not automatically makes a character interesting. There's a difference between a character we love to hate and one we just…want to stop reading about.

A poorly written protagonist might be cruel, selfish, and rude with no depth or justification. They mistreat everyone around them, but not in a way that reveals character. Whether they succeed or fail, we don't care because there's no emotional investment. Readers don’t need to “like” your character, but they need a reason to care about what happens to them.

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Elements of a Compelling Anti-Hero

If you want to craft morally complex characters readers—and the agent—can’t put down, consider these key elements:

1. A Clear Motivation: Show us in a compelling manner why they are this way.

💡 Walter White’s: choices stem from a mix of financial desperation, personal pride, and a need for control.

2. A Fatal Flaw: Every great anti-hero has a weakness that drives them—hubris, addiction, self-destruction, a refusal to change.

💡 Don Draper: His inability to be emotionally honest sabotages every meaningful relationship he has. His talent for reinvention is also his downfall.

3. Create a Compelling Justification System: Show why conventional morality doesn't apply to them. This isn't about making excuses—it's creating a consistent, if flawed, internal logic.

💡 Tony Soprano: Justifies his violent, criminal life by claiming it’s all for his family. He sees himself as a provider and protector,

4. Balance Darkness with Humanizing Elements: Like moments of vulnerability, morals, skills, humor, charm, and a capacity for growth or change (even if unrealized):

💡 Tony Soprano: may be a killer, but he still has a “code” —and he loved the ducks, which symbolize his fears of loss and change.

💡 Don Draper: has occasional moments of genuine kindness (like his mentorship of Peggy) that make him fascinating and, at times, sympathetic.

5. Show Authenticity in Their Darkness: Ensure the negative traits connect logically to their background, feel consistent and serve a purpose in their overall character arc.

💡 Don Draper: His drinking, womanizing, and lies aren’t just bad habits—they’re the core of his identity. His self-destruction is methodical and inevitable. (Hershey’s chocolate anyone…).

💡 Tony Soprano: operates by the rules of the mafia, seeing violence as a necessary evil—even when he tries to be a better person.

Anti-heroes thrive in the gray areas of morality, but they need depth and enough emotional weight to keep readers invested. Walter, Don, and Tony may be awful people—but they’re never boring.

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📌 How Does Your Anti-hero Hold Up?

Determine if you've created a compelling anti-hero or merely an unlikeable character:

1. If this character were a real person, would anyone maintain a relationship with them? Why?

2. Would a reader root for them on some level, even if they disagree with their actions?

3. Does the character have moments of genuine goodness, not just self-interest?

4. Would readers feel anything beyond satisfaction if this character faced consequences for their actions?

5. Does the character have internal conflicts about their choices?

6. Are there legitimate reasons for the character's negative behaviors beyond simple selfishness?

7. Does the character change or at least recognize their flaws over the course of the story?

If you answered "no" to most of these questions, you may have an unlikeable character. Reconsider your approach or make some adjustments.

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