The Dark Side of the Rainbow: 9 Good Guys Gone Very, Very Bad

American actress and singer Judy Garland (1922 - 1969) as Dorothy Gale in 'The Wizard of Oz', 1939. (Photo by Silver Screen C
American actress and singer Judy Garland (1922 - 1969) as Dorothy Gale in 'The Wizard of Oz', 1939. (Photo by Silver Screen Collection/Hulton Archive/Getty Images)

When I told people I had written a book in which Dorothy Gale of Kansas was the villain, almost everyone had the same response: "Uh, what?"

The Dorothy of L. Frank Baum's Oz books is the Little Miss Perfect of children's literature. She's got a sweet, wide-eyed innocence and an ever-optimistic outlook on life. She sees the good in everyone and tries to treat others as she'd like to be treated. Dorothy's got her values in order too: this is the girl who could have been princess of her own personal fairyland, but decided to go back to Kansas instead--because she missed her family.

In the popular imagination, Dorothy Gale is about as Good as it gets. In my book, Dorothy Must Die (HarperCollins, $17.99), she's a vain, evil dictator who needs to be taken out before she destroys Oz.

Where do I get off messing with Dorothy like this? Look, just hear me out.

I like Dorothy, I promise! One thing I love about Baum's character is that, for all her sweetness, she's no Pollyanna. She has a no-nonsense, Midwestern toughness about her that makes her easy to admire. She's a nice girl, sure, but she's not a doormat. Mess with her, and she just might melt you. (By accident, of course.)

Judy Garland's portrayal of the character in the classic 1939 film brings a sense of longing and humanity to the character that makes her even more compelling. Just like most people, Garland's Dorothy is looking for something she can't quite put her finger on, and when she winds up back with Aunt Em and Uncle Henry at the end of the movie, you can't help wondering: is this really a happy ending?

That's where Dorothy Must Die comes in. For me, the idea of "breaking" Dorothy stemmed from imagining what happened once she traveled back home to Kansas after her adventures in Oz. Having been over the rainbow, was she really going to be happy back on the farm? Wouldn't she long for Oz, this magical place where she had become a hero? "Home" would have to pale beside her Technicolor memories. It seems to me that a girl could get pretty bitter once she figured out what she gave up.

Given the chance to make another trip to Oz, I wondered where that bitterness might lead. When an older and maybe-not-wiser Dorothy makes her second trip down the Yellow Brick Road, she makes a promise to herself that she's not making the same mistakes twice--that she's never going home again. I mean, I'd probably feel the same way if I were her. But how far would I be willing to go?

In the case of my Dorothy, she's willing to do just about anything--including dropping a few more houses on people's heads.

I'm not the first writer to nudge a good character over to the Dark Side. From the Bible to Breaking Bad, good girls (and boys) gone bad are a staple in the stories we love. Sometimes the transformation is temporary, like when Superman is exposed to the Red Kryptonite that gives him a bad case of 'roid rage. Other times the corruption is slower and more permanent-- a slippery slope of small ethical compromises that eventually lead to huge ones. It's no surprise that those are the characters I find the most interesting.

Here's are some of my good boys and girls gone bad from books and film, proving just how fine a line there is between hero and villain.

1. Walter White, Breaking Bad. Walter White's metamorphosis from a dying high school chemistry teacher to a meth kingpin is both heartbreaking and horrifying-- partially because we watch every decision that takes him from good to very bad boy. Facing his death from cancer, he puts aside his morality at first to leave a legacy for his family, but as he grapples for power it's clear that he is coming into his evil. Underused and unappreciated in the real world, Walter realizes that he has skills both scientific and strategic that make him the smartest boy in the meth world. His need to be recognized for that skill is what ultimately undoes him.

2. Anakin Skywalker/Darth Vader, Star Wars. When Anakin Skywalker's mom is killed, he's so wrapped up in his own rage that he takes out an entire village. Then he lashes out at the girl he loves and almost kills her. Unable to deal with what he's done, he gives in completely to the Dark Side and the rest is history. You have to wonder what would have happened if someone had just enrolled him in a few anger management classes.

3. Emily Thorne, Revenge. In ABC's Count of Monte Cristo retelling, Emily Thorne is a badass bringing down the Hamptons elite to avenge her Dad's wrongful death. What she's doing is terrible--but then again, they did kill her father. It's only when we see her sweet former self in flashbacks that we wonder if that good girl will ever resurface.

4. Dark Phoenix, X-Men. Arguably the most iconic hero-turned-villain in comic books, kind, polite Marvel Girl unlocks her true potential when she strains her powers beyond their limits to save her teammates and becomes the super-powerful good-time-gal known to her teammates as Phoenix. But soon her newfound power proves too much for her to handle and she eventually ends up eating an alien planet just because she feels like it. Couldn't she have made do with a tray of cupcakes?

5. Nancy Botwin, Weeds. Nancy justified selling weed to support her family's picture-perfect suburban lifestyle, but as the seasons wear on, the compromises pile up, and pretty soon it becomes clear that Nancy's not in it for her kids anymore. There isn't one moment that turns Nancy from good to evil, but by season four she's gotten hitched to a Mexican drug lord and doesn't seem to care that her youngest son just might be a homicidal psychopath.

6. Olivia Pope, Scandal. Olivia Pope is America's favorite fixer. The daughter of a terrorist and the head of the government's covert ops agents, Olivia's DNA may have set her up to walk the line between good and evil. But she is still a good guy--right? I'm not so sure about that. Look, when every single person you know is a murderer, it might be time to question some of your life choices. Olivia might not have technically killed anyone herself yet, but the way Scandal is going, I think it's only a matter of time before we see her pick up the handsaw.

7. The Snow Queen. Elsa from Frozen is based on this classic Hans Christian Andersen villain. Before she was Disney-fied she was the biggest of bads: not a reclusive, girl-powered ice queen, but a formidable villain who wanted to freeze all her enemies. When the original Snow Queen "let go" and found her ice powers, I doubt kids would have wanted to sing along. Anyway, it's kind of hard to sing when you're encased in a block of ice.

8. Willow, Buffy the Vampire Slayer.
When Willow, Buffy Summers's witchy BFF begins to dabble in misusing magic, it's at least understandable. She's trying to get her girlfriend back. Well, we've all been there, right? Unfortunately that's just the beginning. Soon her addiction grows, and before long she's graduated from performing slightly shady memory spells to actually flaying a dude alive. It's only when Buffy and her friends stage a magical intervention that Willow snaps back to her old self, leaving the audience wondering if there's any evil the Snoopy Dance can't triumph over.