Creating great villains is always a challenge, but things get even more complicated when they’re the story’s protagonist. We’re not talking about anti-heroes here, but sociopathic killers and criminals, such as Dexter Morgan and Tony Soprano.

First, let’s establish which Dexter we’re talking about. The Dexter of the TV series was more human than the Dexter in Jeff Lindsay’s novels. The “original” Dexter was far more sociopathic, less introspective, and more violent. He didn’t just kill his victims, he engaged in joyful, creative vivisection. In the novels, the first person narrative is witty and glib, depicting a man who is utterly self-absorbed and so lacking in self-knowledge that he seems oblivious to the self-loathing bubbling just under the surface. In the TV series, Dexter was constantly examining his values, motives, and actions. He was capable of genuine love. He felt remorse. You often get the sense that he was created, not just by his early trauma, but by the perception and training of his adoptive father, and that with the right guidance and therapy, he could have lived a normal life. There’s not a hint of this in the novels. Jeff Lindsay’s Dexter Morgan is a monster. But since he’s working with the “good guys” during the day and going it alone at night to stop criminals who slipped through the legal net, in the context of his story, he’s the lesser of two evils.

So is Tony Soprano. In the first episode, it’s hard to see how a philandering criminal and murderer could possibly be sympathetic. Then we meet his family. His mother is pure evil. She and his beloved Uncle Junior conspire to kill him. His nephew/protege is an idiot and an addict. His sister is batshit crazy and so incredibly selfish that when she decides to marry a recently widowed mobster, she terrifies his children with “messages from their dead mother” to convince her mark that it’s time for him to let go of his wife and move on, for the good of his children. And then there’s his other Family, which he accurately describes as a pack of jackals. Tony has to sustain, support, and survive two untenable social situations. He’s definitely a bad guy, but just about everywhere you look, he’s the lesser of two evils.

Every protagonist needs antagonists. If your protagonist is a bad guy, you have to put him up against people, or situations, that are even worse.

But it’s not enough to be the lesser of two evils. Villainous protagonists also need to have positive traits, qualities that readers and viewers admire and value.

Dexter represents vigilante justice, which is a powerful theme in the American psyche. In many ways, he’s an updated, grittier version of an American folk hero. He personifies rugged individualism and distrust of established authority. When “the system” falls short, Dexter is there to move in and balance the scales. He’s physically powerful, a fit and disciplined fighter. He’s ruggedly handsome. He even follows a code. Replace the Hawaiian shirts with a Stetson, and what you have here is a classic outlaw hero.

Tony Soprano fits another American archetype. He’s a tough guy who has power and money, and there’s a lot of people who find those things more valuable than character. Those same people don’t just shrug off the fact that he objectifies women and has no sexual boundaries, they applaud it. He’s a Real Man, and that’s what Real Men do!  He’s incredibly vulgar, but also capable of a certain charm. He routinely screws over people, but hey, that’s business. He’s a family man with a pretty wife and kids who will probably enter the family business, so he’s got to be doing something good, amiright?  Tony Soprano is a horrible human being, but he’s successful by his own definition of success. We’re fascinated by people who rise to the top, even if–perhaps especially if–what they’re climbing is a toxic dungheap.

Also, Tony has a soft spot for ducks, so there’s that.

When your protagonist is a villain, he still needs to be a human being, with all the messy, complex issues that any hero or anti-hero will be expected to face.

Being a villain does not exempt you from moral dilemmas. TV Dexter was horrified to learn that he’d killed an innocent man, which broke Harry’s Code. Tony Soprano agonized over whether or not to kill his cousin, a decision that forced him to choose between family and Family.  Villains are going to do bad things, and most of the time it’s not going to weigh all that heavily on them. But they do have limits. When your protagonist is a villain, you’ll spend a lot of time finding and testing those limits.

Being a villain does not exempt you from heartache.  TV Dexter came to genuinely love his wife Rita, and he mourned her death deeply. He loved his son and feared that he might have passed along his “Dark Passenger” curse to little Harrison. Most of all, he loved his sister Deborah, and what finally broke him was confronting his part in her fate.  Tony Soprano, worn down by Uncle Junior’s perseveration-level repetition of his youthful failings, burst out with an agonized, “Don’t you love me?” For some villains, the ability to love is a source of pain. For other, it’s the lack of love.

Being powerful does not exempt you from weakness. We want the bad-guy protagonist to win, but they need flaws that will make those victories more difficult and less certain. Dexter is compelled by the urge to kill, and this compulsion can be…inconvenient. He sometimes feels that his Dark Passenger might actually be in the driver’s seat. Tony Soprano’s world is a shark tank, and he knows that his tendency to faint during times of stress is like throwing blood in the water. He needs to appear in control, but being seriously overweight and out of shape tells a very different story.

Bad-guy protagonists can be compelling and even likable, but they come with a built-in dilemma for the storyteller. Given the long-established assumption that Good Will Win, how the heck are you going to END these stories?  Does the protagonist find redemption?  Survive insurmountable odds and come out on top?  Is he brought to justice?  Do you kill him off?

None of these solutions are completely satisfying. We want the villain to succeed and thrive, but we also feel that his karmic debt should be paid. We’d like to see him find redemption, but we also like him as a bad guy.  We want a sense that his story will continue, but we also want closure. We really don’t want to see him in a jail cell, but we know he belongs there. We don’t want him to be killed, even though we know the world would be better off without him. So what’s a storyteller to do?

There’s a reason why Tony’s story ended with an ambiguous Fade To Black. No single choice would have made everyone happy, so the writers let people choose their own ending.  The ending of TV Dexter’s story was almost as ambiguous as Tony’s. (The novels had a very different ending, and I think Jeff Lindsay made the better choice.)

Ambiguity is a fairly common storytelling decision, and in many ways it’s effective. It spawns online debate and water cooler conversations, but it also violates the unspoken contract between storyteller and audience. A story promises several things: Character, Conflict, Resolution. When you deny your audience any real closure, they’re going to feel cheated.

Maybe that’s the point. Perhaps the meta-story message is that nothing good can come of being bad, and the storyteller is saying, “Listen, if you make bad choices, you’ll face undesirable consequences. You chose to become invested in an unrepentant villain, so what did you expect?”  This might be valid and maybe even profound, but it’s hard to pull off.

In summary, if you’re contemplating writing a story with a villainous protagonist, here are a few things to keep in mind:

  • Pick an ending that makes sense to you and is true to the character.
  • Prepare that ending. People are much more willing to accept an ending that doesn’t fit their preferences if they can say, “Yeah, I guess I should have seen this coming because of X and Y and Z.”
  • Sell that ending. Don’t skimp, don’t rush. Whatever happens should happen in a big way.
  • Don’t expect your decision to be universally loved. There is no way to resolve all the conflicting desires and expectations that attend villain protagonists.