Wonkommendations Needed:
Villains Turned Heroes

Hey, Wonkoverse, I need your help! More specifically, your recommendations.

I’ve just gotten a new series proposal assembled, and during the final round of polishing, my agent stuck in a note that read (to paraphrase), “This guy is such a dick. I’ll be curious to see how you turn him into a hero.”

She was remarking on the villain of the first book, who is a colossal dick. Or perhaps more precisely, a manipulative, self-aggrandizing prick. Whatever the flavor of ass-hat, she probably would have assumed he’d get done in by the end of the first story, if not for the series overview informing her he’s the hero of book two. I’m not too worried about de-villain-ifying him, though—frankly I’m looking forward to ripping him apart via hot monkey sex and excessive man-doubt, then reassembling his broken parts into a delicious wreck of an unlikely hero.

But her comment got me thinking: how does one redeem a villain not just enough to make him sympathetic or love/hate-able, but to transform him (or her!) into an actual hero—even a romantic lead? It makes me want to explore the art form, to see how others have pulled it off.

I’m off on a two-week vacation next Monday, the perfect opportunity to suck down some great storytelling. To that end, Wonksters, I want your recommendations for books, movies, and TV shows that boast this characterizational sleight-of-hand—where a villain gets transformed into a hero over the course of a story or series. I’m not talking dick-bag alphas who get broken by the love of a good woman; I mean actual baddies who become lurve-worthy leading men. Think Spike from Buffy, or to a softer degree, Sawyer from Lost. Or non-romantically*, Snape from the Harry Potter opus.

Conversely, feel free to warn me away from villain redemptions that totally didn’t work for you, either because they were too convenient, too unbelievable, or sucked all the spine out of a previously kick-ass heel.

*Non-romantically outside my pants, that is.

About Cara McKenna

Cara McKenna writes smart erotica—sexy stories with depth. Read more >
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59 Responses to Wonkommendations Needed:
Villains Turned Heroes

  1. Audra North says:

    Lisa Kleypas – Sebastian – Devil in Winter. It’s an historical, but he is a MEGADICK in It Happened One Autumn and she still manages to get me all excited about him by the end of DiW.

    • Cara McKenna says:

      BAM!! Thanks, Audra. [scribbles note]

      • Audra North says:

        Awwww, yeah. Also, Hardy from Blue-Eyed Devil (another Lisa Kleypas) though he was mostly nice in the first book, just after another guy’s woman.

        What I’m getting at is that you should just e-mail Lisa Kleypas and be like, “Tell me everything.”

        • willaful says:

          No offense, but these are exactly my classic “didn’t pull it off” books. IMO, Kleypas didn’t actually reform her villains, she simply retconned them.

          • Erin Satie says:

            Agree 100% about this. I absolutely adored Kleypas’ St. Vincent when he was a villain. I hated him as a hero. Thought he lost all the qualities that made him attractive to begin with.

  2. Edie says:

    Kaleb Krychek in Nalini Singh’s most recent Psy-Changeling installment, HEART OF OBSIDIAN. He is absolutely villainous in all of the books leading up to his, and I appreciated that he didn’t really become any less terrifying in his own book.

    My first thought was the same as Audra’s—Sebastian is always my go-to baddie, and DEVIL IN WINTER is perhaps Kleypas’s best historical. She has another bad-guy-turned-hero historical, Nick Gentry in WORTH ANY PRICE, but Nick isn’t quite as villainous as Sebastian in the books leading up to his own.

    And, though I hate to be a pusher, Gaspard in my CORRUPT COMTE is…not a good guy. Spy, criminal, murderer. He’s fairly Spike-y (a la Buffy), if Spike were a supposedly homosexual faux-aristocratic Frenchman in 1820. :P

  3. Eliza says:

    Lord Vaughn is a cold-hearted bastard who lurks around in books 1 through 3 of Pink Carnation, then gets his own book (surprise!) in book 4, The Seduction of the Crimson Rose. You don’t need to read all 4, but if you do the payoff is worth it to see how the author keeps his character consistent in all the books while still making him a hero. What I hate about “dick + love-of-a-good-woman = hero” is that it usually means some rewriting of character. But both the hero *and heroine* of the book 4 are both antagonists from previous books and keep their lovely prickly personalities in book 4 AND deserve their HEA. One of my favorite in the series, aside from Blood Lily (book 9).

  4. Does it come down to motive and self-awareness? I’m thinking of Lori Foster’s Rowdy here. He comes off as a total controlling ass in the first book he’s in, but he’s the hero everyone loves by book three. For him it was motive. In trying to protect his sister he became single-minded and domineering. Then, after other folks started helping with his sister and he realizes how hard it’s been on her, he chills a bit.

    However, an early scene in the book he’s a hero in has him fucking some other broad and the heroine walks in on him, so he’s still got some redeeming to do.

    • Cara McKenna says:

      Yeah, I think motive is totally key. I suspect that a great number of villains-made-heroic will have to have been [subjectively] evil for really good reasons—their cause to them will feel as righteous as the good guys’ cause. That’s one flavor of redeemable villain: the kind who doesn’t regard himself as a villain. (See Magneto.)

      Then I think there’s another flavor. The villain who is self-serving, greedy, opportunistic, maybe even evil, but then suffers a life-changing event that knocks him for such a major loop, he can’t continue on the way he has been. Maybe his selfish pursuits cause him to lose something or someone he truly cares about, and he’s forced to reexamine the path he’s taken.

      I don’t think there’s any single way to pull it off…but I bet it does boil down to a core handful of scenarios.

  5. Meagan Day says:

    If you enjoy a good paranormal, Kresley Cole turns a flat-out evil character into a hero in Lothaire.

    • Cara McKenna says:

      That one’s intrigued me for some time—thanks! I’ve only read Cole’s historicals, though I loved every one. Okay to skip all the way to book 12 in the series, or do I need to read the earlier books to appreciate his evol?

      • Meagan Day says:

        They can stand alone, but like any series it’s richer if you’ve read them in order. Lothaire (who’s called The Enemy of Old, so you know he’s legit evil) first shows up in the series opener, my personal favorite, A Hunger Like No Other. His appearance is brief, but he plays a slightly larger role in Kiss of a Demon King, and then starts getting some depth in Dreams of a Dark Warrior. But I think there’s enough backstory in her books to just jump in where you like.

      • willaful says:

        Oh speaking of Cole, I’d recommend Dreams of a Dark Warrior though it isn’t exactly what you’re looking for because it has the villain becoming the hero (in the same book.)

  6. Nicola O. says:

    Loretta Chase has some pretty good redemptions. IIRC, the villain from The Lion’s Daughter becomes the hero in Captives of the Night, which is one of my all time romance favorites.

    Into the Shadow by Christina Dodd has a good redemption arc, although you can’t quite call Adrik a villain, I don’t think.

    • Cara McKenna says:

      Yeah, it’s a squirrelly request, since so often the line between villain and everyday ass-hat can be quite blurry. In this series I’m plotting, the guy is the public face of the villainous forces in the first book. But his bosses are more evil than him, and more evil than he realizes until book two, when he suddenly feels like a pawn. He’s a sort of…posh henchman, I’d say.

      • sofia says:

        Maybe you should try out Stacia Jane’s Downside series. By the nature of his job (Chief Enforcer to a Drug Lord) Terrible is bad, but inside he is totally hero material.

        • sofia says:

          STACIA KANE not Jane.

          • Erin Satie says:

            I adore Terrible. He’s one of my all-time favorite romantic leads. But he’s never a villain–he doesn’t change, or get ‘redeemed’. He’s still the same person he started out as, and so far there’s no suggestion that he’ll ever quit.

            Even though he spends his days beating up addicts to collect money. And is in love with an addict.

    • Meri says:

      Another vote for CotN, though it should be pointed out that Ismal/Esmond’s transformation pretty much happens off-screen, between the two books.

      If NA is okay, Reid Alexander from Tammara Webber’s Between the Lines books is a really good example. He is awful for most of the first two books but becomes a believable good guy in the third.

      Not that they’re really romance novels, but Rupert Campbell-Black in Jilly Cooper’s books qualifies. He is horrible in Riders and while he never becomes a nice guy, he does become a better person in various ways.

    • Captives of the Night is awesome! In a way I see Dain from Lord of Scoundrels as a bit of a villain turnaround. He’s a complete dissipated wanker bent on destroying the heroine’s brother for fun at the beginning of the book, but I totally buy his redemption by the end (LoS is my favorite Chase and a desert island keeper for me, I admit).

  7. A.J. Larrieu says:

    Ooo, I love a good switch hero. Vivi Andrews has one in Super Lovin’. He’s an actual comic book-style super villain turned good…but he was pretty good to begin with, so this may not be the big bad-to-good arc you’re looking for. Still–I enjoyed the book.

  8. sofia says:

    The Black Moth by Georgette Heyer features the bad Belmaniour, who leaves you wanting to redeem him.

    • HJ says:

      Yes, Belmanoir is the forerunner of the Duke of Avon, the hero of her later book, These Old Shades. He’s been a pretty bad chap but is redeemed when he falls for Léonie who is disguised as Léon. Even when he rescues her he does so to use her as a weapon against an old enemy, but he becomes intrigued by her then falls in love with her, and eventually his motives become mixed, wanting to revenge the wrongs done to her as well as score against his enemy. Heyer does the process of redemption quite well.

  9. Corina says:

    Let’s see … I’m not entirely sure I get the line between *really* bad and just douchebag Alpha, but I’ll try to stay on the right side of that line. In Anne Stuart’s Ice series the heroes are pretty horrible people. They’re arms dealers, assassins etc. They work for an agency that is, ostensibly, the good guys but they do some terrible things before they end up with their HEA. In Black Ice the hero lets the heroine (who he’s already seduced(?) in the course of business) be honest–to-god *tortured* before he gets his act together and rescues her. None of her heroes in that series ever really lose their essential coldness and ability to do truly awful things. (Or let truly awful things happen.)

    In the realm of television, what about Logan Echols on Veronica Mars? He’s no soul-less vampire (or arms dealer), but he does some very not-good things over the course of that series, and is never a really *good* guy, but he definitely improved to the point where I could see him as a legitimate romantic prospect.

    • Erin Satie says:

      You know, if we’re talking about heroes who would be bad guys *to the reader* (versus acting as villains within the plot line of the novel), I’d suggest Manna Francis’ THE ADMINISTRATION series.

      It’s original, online fiction. M/m. And once I started it I *could not stop reading*. Thought it was utterly amazing.

      But the hero is a torturer (like…that’s his 9-5) & although he’s never the villain to his beloved, pretty much everyone else would say he’s an evil bastard and garden variety villain.

    • Kate D. says:

      Yes to Logan in Veronica Mars! I just re-watched season one and was amazed at how much of an asshole he actually is. My lingering impression of him from watching the show years ago had been of a tragic hero. Love that show!

  10. Liz Mc2 says:

    I’m kind of surprised that no one has mentioned Patricia Gaffney’s TO HAVE AND TO HOLD yet. Maybe it’s because people who love that book never see him as a villain? I did–and I think Gaffney’s protrayal of his cruelty to the heroine is masterful psychology. (Maybe he’s not exactly a villain, but he *is* someone who isn’t sure he can make the effort to be a good guy, and who thinks he’s on the road to being a villain, and not just in regard to the heroine/women). The transformation didn’t work for me, but many people I respect cite this as one of their favorite romances and I’d say it’s required reading on this subject. Even though I didn’t love it and wasn’t persuaded by it, a lot of it blew me away.

  11. Jessi Gage says:

    I think the key (or one of the keys) to redeeming a villain is finding out what their motivation is for being evil. Is it some insecurity the perfect heroine will help him discover and address? Is it a pattern of abuse from the past?

    I’m looking forward to you redeeming a bad guy, even if the result isn’t all cuddly and fuzzy and fit for consumption. Sometimes redemption can just mean making your character lovable by one, the heroine, not necessarily by all. (Though the reader probably ought to love him, LOL!)

  12. I kinda think Allegretto from Shadowheart qualifies; he’s a killer but he … well, it’s complicated. Never mind.

  13. SonomaLass says:

    Carolyn Jewel’s historicals, Reforming the Scoundrels (Not Wicked Enough and Not Proper Enough) do this well.

  14. Jennifer Ashley has 2 I can think of off-hand. One is a dragon PNR where the hero of book 2 (BLACK DRAGON) was book 1’s (DRAGON HEAT) villain:

    And WILD WOLF which is part of her Shifters Unbound series.

  15. While not necessarily romantic leads, I’m intrigued by TV characters who are “bad” (hard to get along with, morally bankrupt, ethically challenged, hardarses) but still somehow likeable.

    Eric in True Blood, House, Dexter, The Wire’s Stinger Bell, Breaking Bad’s Walter White, GoThrones, Jamie Lannister, Mad Men’s Don Draper. In some case the character anchors the show, yet they’re rude, crude, lying, cheating, thieving, murdering scoundrels – and we tune in every week for more of their badness.

    Each of those bad guys has some outstanding redeemable feature: crime to secure family, murder justified by the failure of the system to be just, miracle cures in exchange for narcissistic behaviour, redemption from disablement.

    The way they teeter on the bad guy/underdog/good guy ledge is fascinating. Episodic TV has hooks that are harder to engineer in novels, but still by and large these guys don’t reform completely (until the series end deals with them) and yet we cope with them because of the weight of the redeeming feature.

    There has to be something in that – but while it works for TV, is it enough for a romantic novel, because while we hope Dexter gets away with murder, Eric doesn’t really go up in flames, Jamie becomes a hero worth following, would we ever learn to trust them in a HEA sense?

    • Cara McKenna says:

      I nearly referenced Eric Northman in the post, but couldn’t quite nail him down as a true villain. An antagonist, yes, but not a true villain or henchman, in my estimations… It’s all semantics, I know!

      Jaime’s a great example. Tricky with GoT, since labeling villains and heroes means picking a side, Stark vs. Lannister, and they’re all so deliciously righteous in their own minds, since Martin’s a genius. But I’d argue that in the first book or two, Jaime is pretty much a villain. What with the attempted child-murder and all. And his arc thus far in the books has been really amazing. I could totally see him turning straight-up admirable at some point, thanks to all the whatnot with Brienne.

      Joffrey on the other hand…now that little shit is one villain who could never be redeemed!

      • Eric is a bit slithery. And Joffery! Ah Joffery, he gets his – but it’s not exactly redemption. I’m holding out for Jamie to become heroic – or possibly dead (Nooo!) as is Martin’s way.

        I’ve already started trawling this reading list. Great post

        • Cara McKenna says:

          I’m fascinated by how many historicals are getting recommended! Makes me wonder, do people just read tons of historicals, or is there something inherent in historicals that makes for a more fertile villain-to-hero environment?

  16. Erin Satie says:

    This is one of my very favorite tropes. I love villains who become heroes.

    My very favorite example of this trope is the Hollows series by Kim Harrison & the heroine has really intense chemistry with the villain for…oh, eight, nine books? I mean, the villain has a lot of time to dig trenches and fire artillery at the heroine. But the enmity gives way to a hostile working relationship, and that leads to trust, and that leads to love…it’s the best. And they really earn it–by which I mean, it takes 12 books for this one couple to get there.

    In Carolyn Crane’s DISILLUSIONIST trilogy, the hero switches roles so many times–he starts out as an ally but becomes a villain before he’s redeemed (Uh…spoilers).

    In Megan Whelan Turner’s Attolia series, the hero and the heroine are enemies–the heroine is the villain of the first book, actually. So there’s a nice genderflip.

  17. Rhyll Biest says:

    I can’t wait to meet your ‘dick’. Wait…that didn’t come out how I meant it. Anyways, I really liked Ian in Skin Game and he was a total dick, so, um, dicks can be loveable, right?

  18. HJ says:

    My view is that the reader will only believe that a villain has become a hero if she can be persuaded that he wasn’t really a villain in the first place. In other words, his motives for behaving like “a dick” (to quote your editor) will have to be convincingly good ones if he is to be transformed subsequently. You may want to ensure that nothing in the first book will make it impossible for the reader to believe in those good motive when she learns of them in book three.

    Also, even with good motives, I don’t think a reader will be able to forgive truly mean or evil behaviour, so his “dickness” had better be stuff which can be forgiven ultimately.

    • Erin Satie says:

      Personally, when I want a villain fix, I want a REAL villain whose actions are morally grey (maybe dark grey, maybe black).

      I like good guy heroes, too. But I hate villains who are secretly good guys. That will make me throw a book across the room.

      But I have come to realize that my interest in morally irredeemable heroes is a sort of niche thing, and that heroes who really suit that taste are hard to find. I think most readers would agree with you, HJ.

      But not me! I say, bring on the bad guys.

  19. Cara McKenna says:

    Holy crap—you spoil me, Wonkoverse! I can’t jot these all down fast enough.

  20. Audra North says:

    I’m going to go ahead and offer it up, and feel free to laugh hysterically, but Gru from Despicable Me is my fave big-screen villain-turned-good-guy.

  21. Jackie Horne says:

    Patricia Veryan’s THE DEDICATED VILLAIN (another historical!)

    And I’d second the recommendation of Megan Whalen Turner’s YA THE QUEEN OF ATTOLIA; you need to read THE THEIF, first, in order to appreciate it, though…

  22. MaryK says:

    On the unredeemable front, Linda Howard had an arms dealer villain in All the Queen’s Men who seemed to be being set up as a future hero. I saw much negative push back to that idea on the web and I wouldn’t have read the book. His villainy continued too long after he could’ve conveniently changed his ways. IIRC, he got into the business because he needed money for his ill daughter, BUT he continued in it after he made his fortune because it was lucrative. He was generally considered irredeemable.

  23. Keller Anne knight says:

    Ditto Anne Stuart. Any of her “men who kill” never really become good guys. They just have a huge capacity to love the heroines.

  24. sofia says:

    True redemption comes from inside, because we truly want to change not because it is a requirement for something else we want, for example the love of another.

    There is also the possibility that although on the wrong path, redemption is not sought. Choices are made and then kept.

  25. willaful says:

    Has anyone mentioned Death Angel by Linda Howard? I haven’t read it in awhile, but IIRC the assassin hero reforms (sort of) because of a spiritual experience, which is kind of novel.

  26. willaful says:

    I just finished Beloved Killer by Bonnie Dee. The hero is a mob enforcer who tries not to think too hard about what he does. I think he has a pretty plausible redemption.

  27. Cara…I just realized. You’re watching Sons of Anarchy and yet you need more examples of villain heroes? You’re watching Sons of Anarchy.

  28. jmc says:

    Lurker here, posting late.

    Patricia Veryan’s Golden Chronicle series, which is set in Georgian England following the Jacobite uprising and the battle of Culloden, ends with The Dedicated Villian. TDV is the book of Roland Otton, who spent the first five books (I think he appeared in most or all of them) being pretty despicable. The series is older, published in the late 80s and OOP. I read it years ago, so I’m not sure if my perspective would be the same now that I’m more widely read, but Otton stuck out as being truly a villain, unlike many sort of villainish characters whose villainy is easily explained.