D. B. Jackson’s acclaimed historical fantasy Thieftaker features a remarkable female character who challenges any and all notions of gender roles in the time and place in which she lives, 18th century Boston. She holds a position of authority. She’s good in a fight. She wears trousers. She owns her sexuality. She’s free from all romantic encumbrance. She’s the kind of woman I would want to take to my heart. There’s just one problem.

She’s the villain.

“Villain” is an abstract term, with different meanings for different people. Fictional villains — the interesting ones, at least — don’t perceive themselves as villains. In their eyes, they are heroes with ends which they must achieve at all costs. Sometimes the line between hero and villain can be difficult, if not impossible, to find, especially in the fantasy subgenre called “grimdark” these days. Nonetheless, here’s what separates the villain from the hero, for me: the villain is okay with the concept of “collateral damage,” and even thrives by it. Villains will injure or kill countless innocents without a shred of remorse if they think it will help them achieve their goals. Some villains bulldoze over innocents in the name of love, as Cersei Lannister’s twisted brand of maternal devotion leads her to commit atrocities (or at least wink at them) in George R. R. Martin’s popular A Song of Ice and Fire series. Others are sociopaths, incapable of any love but self-love; the trouser-wearing take-no-prisoners villainess of Thieftaker may fall into this category.

Plenty of readers, some of them friends of mine, adore female characters like these. Some female readers perceive them as empowering, since they are unafraid to seize power by any means necessary, and as they do so they strike terror in the hearts of the men unlucky enough to come into contact with them. I can see the appeal. Such women are fascinating in their unpredictability, in their willingness to break all rules, including the rules of common decency. Empathy and self-sacrifice, long considered crucial components of the Feminine Ideal, are missing from their make-up. Yet even though I may find villainesses intriguing and even entertaining to read about, I can’t find them empowering. After all, the villainess may be a terrifying force for a little while, but eventually, she has to lose the battle. And in so many stories, including the Thieftaker series, she must lose to a man in whom power/authority and common decency manage to co-exist. The Righteous Man must triumph over the Evil Woman if the world is to be saved or justice served; nascent notions of feminism must be squelched.

Villainesses are not an outgrowth of modern-day feminism. They are as old as the ancient world. In the oldest existing epic, Gilgamesh, the only important female presence is a wicked temptress of a goddess. In ancient Greece we find the likes of Medea and Clytemnestra. (The husband Clytemnestra kills sacrificed their daughter to the gods for a fair wind to sail to Troy, but we’re clearly supposed to be okay with that; her actions, not his, are presented as evil.) In the stories of King Arthur we have evil witches like Nimue and Morgan le Fay, whose contrast to the benevolent male sorcerer Merlin suggests that magic can only be a force for good if a man wields it. (This idea was once so deeply ingrained in the fantasy genre that even the feminist author Ursula K. LeGuin unconsciously made it a part of her original Earthsea Trilogy: “weak is women’s magic”/”wicked is women’s magic,” as the saying goes.) Shakespeare gives us Lady Macbeth. Dumas gives us Lady de Winter. William Makepeace Thackeray gives us Becky Sharp. Moving into the mid-twentieth century, C.S. Lewis gives us the White Witch and the Green Witch. All are clever. All are ambitious. All are evil. They are the forces from which the world must be saved — by men/boys, of course. (Becky Sharp offers an interesting exception in that she is not defeated by a male hero but is allowed… almost… sorta/kinda… to win, or at least evade justice.)

For centuries we’ve seen power and goodness written as incompatible in female characters. For a woman in times gone by, to be good was to be passive, mild, unambitious, selfless, nurturing. A good woman did not rise up to confront the villainess. Rather, her virtue showed itself in her willingness to rely on a man to solve the problem. Powerful men may protect, defend, and rescue. Powerful women could only destroy. I can’t quite manage to find any satisfying feminist underpinnings in this.

Today’s speculative fiction shows matters have improved considerably, though there is still plenty of progress to be made. Female characters on the side of Good no longer have to stand passively by and rely on men to save the day or the world. Plenty of excellent novels, many of which I’ve mentioned on this blog, show that female characters need not crush their moral compasses underfoot in order to be active, capable, and even powerful. Villainesses still have a role to play, perhaps now more than ever. But how enjoyable I find a villainess in the books I read today depends heavily on what the heroine is doing.

If we have a heroine who is as powerful and capable in her own decent way as the villainess, and indeed is the chief agent of the villainess’s downfall, then I can relish said villainess’s evil antics without the uncomfortable sense that I’m about to witness an “uppity woman being put in her place.” Examples: Elizabeth Bear’s Eternal Sky trilogy, starting with Range of Ghosts; Juliet Marillier’s Daughter of the Forest and Heart’s Blood; Sharon Shinn’s Twelve Houses series, starting with Mystic and Rider.

Likewise, if the heroine or heroines are part of a team, all of whom contribute substantially to the triumph of good, then I can sit back and enjoy the villainess doing what villainesses do. Quite a few episodes of the excellent (and sadly cancelled) animated series Justice League, Justice League Unlimited, and Young Justice offer examples of this.

If the heroine is only an occasionally useful sidekick to a male hero, I start to enjoy the Evil Woman a little less. If said heroine is a touch feisty but is nonetheless held up as a conventionally feminine contrast to the butt-kicking bitch on wheels, my enjoyment is diminished still further. Quite a few James Bond films fall into this latter category, most notably A View to a Kill.

If there is no heroine to speak of — if she’s little more than a love interest and plays no role in the villainess’s downfall, or if she has little more than a walk-on part, or if there is no female character on the side of Good at all — then I will most likely seek my entertainment elsewhere. (Examples: Orson Scott Card’s Pathfinder series; Myke Cole’s Shadow Ops series.) These may be very good books, and I don’t mean to encourage my readers to avoid them; my hang-ups are my own. But with Righteous Man vs. Evil Woman, I’m afraid I still can’t even.