This month I thought I’d take a look at some of the bad boy heroes of Romance.

I’m not talking about common-or-garden variety bad boys, here. That strain, the rebellious, troubled men, often misunderstood and usually returning from years spent away, are a staple of the genre.  They have a satisfactory character arc and generally provide a good plot impetus for a quieter sort of heroine.  They are the basis of hundred of books, dozens of songs, and any number of movies.

That’s not who I mean. I’m talking about the seriously bad. The criminal.

That’s a tough character choice.  The writer has to make someone who already has already demonstrated that he has no respect for the law and by extension, public welfare, into the hero.  That’s hard going. Thing is, when it works, it works really REALLY well.

Thievery is one of the most common criminal career choices in Romance.  It offers a wide range of possibilities and a small chance of violence. Most of heroes of this type chooses deliberately to avoid weapons, and not just because armed robbery carries a high sentence.  They’re in it for the game, for the allure of sneaking in and coming out on top. John Blackheart, hero of two Catspaw novels and a novella by Anne Stuart, is that kind of thief. What he likes it the challenge. And when it becomes more challenging to go straight, he does. Blackheart is actually a security consultant in the books: his past as a renowned jewel thief is one of his top selling points. And of course his light-fingered skills get a lot of use during the stories, whether he’s trying to clear his name, rescue a family member, or just tease the heroine, Francesca.

Philip Chamberlain, hero of Nora Roberts’ Sweet Revenge, is another thief who turns thief-hunter. We actually follow his career for many years, from his late teens to his thirties. Philip is a cat-burglar from the Cary Grant school of larceny: suave, sophisticated, and sleek. He lives the high life and takes good care of his mother. Interestingly enough, he also makes the cool and logical decision to stop being a thief and instead help Interpol catch other thieves. Which is how he meets Adrienne al-Jaquir, daughter of a Middle-Eastern ruler and a Hollywood actress. And a pretty good thief herself, though she steals strictly for the practice, selling what she steals and giving the remains to charity, minus a only small commission for living expenses.

The Robin Hood effect, stealing from the rich and giving to the needy, still resonates with readers. Possibly even more today than a couple of decades ago.  If a thief-hero targets, say, only socially irresponsible companies or their greedy C-suite personnel, he seems downright noble.  That’s the tact Connie Brockway takes in her Regency novel All Through The Night. Though the thief is this case is the heroine, Anne Wilder.  Anne runs a charity for wounded soldiers, those men who were badly damaged in the Napoleonic Wars then abandoned by their government when they returned (plus ca change, eh?).  She targets rich members of the ton who publicly promise to support her work but privately renege on the deal. From them, she steals what they claim to have given. Colonel Jack Steward is sent to apprehend her, which doesn’t go quite as his superiors have planned.

Another books in which things don’t go as the shadowy men in charge would like, is Agnes and the Hitman, by Jennifer Crusie and Bob Mayer. We’ve talked about this book a lot on the Gutter: carol, alex and I have all written about it. Which tells you a little something about the novel’s reach and impact, but that’s another subject. Currently, the subject is Shane, the hitman of the title.

Who is a killer.

It’s important to recognize that. There’s no accident, no misunderstanding: Shane kills people.  It’s a job, one he does at the behest of the US government.  As he says of his employer, “It send [people] to war and it sends them to the electric chair, and sometimes, when it wants to be more efficient and merciful, it sends me. I’m more more precise and efficient than a bomb dropped from ten thousand feet.”

There’s a lot of cogent social criticism packed into those two sentences, but that, too, is another subject. The thing about Shane is, he’s tired. This military-school graduate, and commended black-ops fighter is weary down to the farthest reaches of his soul. The deliberate taking of lives, however horrible the victims, has ground him down. Meeting Agnes helps him realize that he wants his life to change. So he begins to make room for his own choices, his own desires, instead of just obeying orders.

That moral code, that sense of right and wrong – however skewed – is one of the things that make books with criminal heroes and/or heroines so compelling.  Not just because reformation is narratively powerful (although it is) — sometimes the criminals don’t reform at all.  Simon Goodnight, from Linda Howard’s Death Angel, is an assassin.  He kills people for money. He’s very good at it, too, in his own twisted way, he’s a master craftsman.  It’s pretty clear in the text that Simon is a sociopath. Not in the sense that he thinks of all other people as toys and/or obstacles; rather, he has absolutely no moral qualms about killing people. None. Granted, he’s generally hired by criminal organizations to kill other criminals, but still. He’s cold, emotionless, and hard to take as a Romance hero. Until he’s sent to kill Drea Rousseau, the former mistress of a drug czar… and a woman with whom he once had a one night stand. What happens next surprises everyone, including the reader.

As  (super brilliant) author Patrick Ness said in a recent Twitter discussion about YA literature:  “I believe that if you don’t engage with darkness, you’re leaving a teen alone to face it by themselves. I think THAT’s the amoral position.”  The same goes for Romance.  Death Angel was a tough book, but remarkably satisfying. Neither Simon nor Drea are likeable people. In fact, they’re kind of awful. But they both choose to make something better of themselves, something worthy.  And it’s because they have so very far to go that their journey is valuable.

Even though she paid it back, Chris Szego still feels guilty about the time she stole 50 cents from a fountain.