Previously: Favorite Character: Dean Winchester Is A Douchebag
Least Favorite Character: John Winchester
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I’ve struggled with this week’s challenge, because as vile as I find many of the characters – Zachariah, Alastair, Meg, Lilith, Samuel Campbell – that, of course, is the point: We’re not supposed to like villains. As sources of conflict, they’re supposed to repulse and disgust, and from a writer’s perspective, I can appreciate Supernatural’s antagonists for doing their job, and doing it well.
The one exception is John Winchester, for whom later seasons go through great pains to make sympathetic. Whether or not it works varies by viewer, I expect, but as time wears on, and my own complicated relationship to my parents evolves, I find myself making fewer and fewer excuses for the man. I appreciate his role as an antagonist, to be sure, but he’s not a villain, not like the others; and honestly, if he were real and I were ever to meet him, I think I’d kick him right in the nuts.

Let me be clear: I don’t think John Winchester is a bad man—or, rather, I don’t think he starts off that way. But then again, demons never do. At one point, every scion of Hell was human, and that’s what makes their fall from grace so sad. And if John Winchester fell further than most men, it was only because he became so obsessed with being good at falling that he forgot to learn how to land.
Major spoilers for Season 1-2 Below, Minor for Seasons 3-6:
Welcome to the inaugural “Meta Thursday”! I’m kicking things off by starting up a new 30-Day Challenge, this time for “Supernatural” (of course)—although “30-Day” is a bit of a misnomer, because I don’t plan to do more than one of these essays a week, given that the Dragon Age one nearly killed me. :) I know many of you don’t watch Supernatural, or have (very valid) objections to its often problematic representations of women/POC, but hopefully I can address a few of those concerns and maybe get a few of you to check it out, because despite its flaws, it really is one of the best shows on TV today.
Enough blather. On with the meta!
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Day 1: Your Favorite Character

Dean Winchester is a douchebag.
He’s cocky. Sexist. Petty. Judgmental. In early seasons he’s a bully. In later seasons he’s a drunk. He’s not particularly smart, or clever, and he thinks his jokes are much funnier than they really are. Often he tries too hard to be sexy, or cool, or manly, and as a result, he comes off fake, even desperate. He’s incapable of relating to women as real people, or, for that matter, men. He’s a “C-“ in bed that thinks he’s an “A+”, and he probably smells bad from all the cheeseburgers and liquor and sitting around in cars. He’s codependent, emotionally constipated, terrified by real intimacy, and lonely, so intensely, painfully lonely, that he pushes everyone away, or marginalizes them by turning them into a victim or someone he has to protect, because then his feelings too can be marginalized and contained; because to Dean Winchester, nothing, nothing, nothing in heaven or earth is more frightening than the most basic human endeavors of trusting, loving, or meeting someone halfway.
Also he’s addicted to hentai—which, dude, seriously?
Dean is all of these things and more—he is “a great big bag of dicks” as a certain Trickster might say—and yet, somehow, surprisingly, I love him anyway.
Very early on, despite his many flaws, Dean became my emotional anchor in this show instead of Sam—who, as a Hero on a Hero’s Journey, embodies the very archetype of relatability. And it doesn’t matter that Dean’s collection of foibles is almost custom-tailored to piss me off, because while I can’t excuse his flaws, I still accept them. His flaws give my love something to stick to.
Why do I love him? Easy: Dean Winchester is one stubborn son of a bitch.
No matter what he’s up against, not Heaven, not Hell, not Sam, not even himself, he doesn’t give in or give up. He might flinch, he might get scared, he might flee Hell Hounds or demons or God when He takes a familiar face, but Dean Winchester never, ever cries uncle. He sasses off to the Reaper and insults the Host of Heaven and shoots the devil in the face, because as he says himself, “I never did know when to quit”.
Sure, Dean Winchester has a few other admirable qualities – his loyalty to Sam and his adopted family, his taste in music and movies, his rational skepticism and cool under pressure, and of course, his talent for nurturing — but it’s his stubbornness, I think, that precludes all others; it is his saving grace, the reason for which he always deserved to be saved.
— Spoilers for Season 3 and beyond after the break —