Supernatural‘s Dean Winchester Dismantled His Own Machismo—and That’s Why We Love Him

Whenever a television show makes it beyond four of five seasons, viewers have cause to be impressed, but commonly worried as well; often a series has played out their greatest themes by then, most of the arcs have come full circle, and whatever the narrative was trying to say has been shouted at you, or possibly sung as a libretto. It’s done its thing, and now wants the three act play to become six or possibly twelve acts.

Supernatural is on its way to a ninth season. And besides finding new, improbable ways to keep their universe fresh and untested, the show also seems to have realized the key to infusing the story with new life—by allowing its main characters, who started the show at ages 22 and 26, to grow up. And what that has meant for the eldest Winchester brother, Dean, is a glorious transformation from posturing, macho alpha dog to… well, something that is no longer capable of being pared down into a caricature. It’s been an awesome ride.

At the start of Supernatural, Dean Winchester is markedly a “type.” Doesn’t matter if you love the guy, it’s unavoidably true. Dean is the bad boy, the kind that pop culture tells us “women want and men want to be.” He’s an incorrigible flirt and prefers his ladies fast, he barks and scowls when he’s not in charge, and when you’re in his car, it’s his rules, and you listen to his music the whole way. He likes guns and beer and bad fast food, and you’d never catch him in a pair of hipster jeans. He makes fun of his little brother for being a nerd (i.e. “reading books”) and his bravado is right up there with Han Solo and Mal Reynolds. Sure, he’s a little goofy and mired in crippling feelings of worthlessness and doubt, but that’s not what he shows upfront. At first glance, Dean Winchester is a throwback of the decidedly cowboy variety.

Supernatural, Dean Winchester, Sam, John

But as the series continued, more subtleties were brought to the surface. We found that most of his machismo was a front, a lot of it learned from his father, a marine who raised his boys to be supernatural hunters. With a distant dad he was desperate to impress, Dean took on a lot of his father’s tastes, likely in hopes that he would be praised and noticed. John Winchester did love his sons, but he was never very good at being present emotionally for his kids, as we see bluntly when they reunite with him in the show’s first season. In an effort to feel closer Dean learned to love his dad’s music, treated his vintage car like a person (to be fair, the Impala is their home), wore his leather jacket, and followed John’s rules to the punctuation.

But Dean Winchester is not very much like his father, and as the show went on, we were carefully shown the dichotomy between them. In fact, once John passed, the show diverted a lot of effort into deconstructing the Great Myth of Papa Winchester. It is an act that Supernatural is still busy with, as more of Sam and Dean’s family heritage comes to the forefront and we find out how little John knew about the world he threw his sons into. We learn that Dean is far more like his mother, who came from a family of hunters, and that John’s own missing father was a Man of Letters, a group that busied themselves with the study of all things that go bump in the night. Dean mimicked his dad because he was present, but had he been raised with his mother around, he likely would have felt no need (not to mention that John would have undoubtedly been a better parent if Mary had lived). John’s death is the start of Dean’s road to adulthood, to becoming a person who has to make his own decisions without guidance and pave his way in the world.

Supernatural, Dean Winchester, Sam

But part of being an adult is wrapped up in still fulfilling the single most important order his father ever gave him: Taking care of Sammy. With John away on hunts, driven by revenge and grief, Dean was always the primary caretaker of his little brother Sam, essentially filling both parental roles all throughout his childhood. What is fascinating about having this responsibility thrust on him so early in life, though, is that it carves out the core of Dean’s character—the compulsive need to take care of the people who matter in his life, no one more than Sammy. He expands that impulse to include more people every year, to the point of ignoring his own health and happiness.

It isn’t hard to figure out why he keeps at it, either—his familial instinct seems to be one of the main things keeping him and his brother alive. Dean’s true strength isn’t to drink-and-drink-and-lead-and-fight but to love the people in his life so fiercely that they cannot let him down. The show has a history of characters overthrowing mind-control and demonic possession (something that is practically impossible to do in nearly every other instance, and Sam had it doubly hard because he was possessed by Lucifer) because Dean loves them so much that they can’t bear to hurt him. It happens to his father, to his brother, to Bobby, and most recently to Castiel. We see the angel brainwashed to kill thousands of simulacra, all of them very real, but when it comes time to murder Dean, one honest plea of “I need you—we’re family” stays Cas’ hand.

Supernatural, Dean Winchester, Castiel

Doesn’t quite sound like your typical hyper-masculine-fueled Fast and Furious rodeo anymore, does it?

With Dean’s heart in the right place and John’s shadow no longer looming, Supernatural also made moves to tackle the surface attributes that painted Dean as a cliché and drown them. When season three antagonist Bela sizes Dean up in a tux, he huffily tells her not to objectify him, which at least lets us know that he’s clear on the act of objectification and the ways in which he also participates in the practice. His self-loathing eventually becomes more prevalent, leading to a personal awareness that keeps him evolving. When Dean finds himself the prey of a fear sickness in the episode “Yellow Fever,” he blurts out all sorts of uncomfortable truths to his brother, including the admission that he knows he annoys Sam, that his taste in music is limited, that he drives too fast. He doesn’t rid himself of those habits, but they are no longer the hallmarks of his person, and we watch that transition germinate over the years.

As it turns out, Dean is the better keeper of nerdy pop culture references—last season he memorably explained to Sam that no, the angel Metatron was not Megatron the Transformer—so calling his brother the geek in the family is an argument of semantics at this point. He happens to think Dirty Dancing is a fine film because, you know, Patrick Swayze is in it. (Do Ghost and To Wong Foo, Thanks For Everything get a pass too, then?) We learn that he’s a damn good cook where Sam had been sure he’d never stepped foot in a kitchen. We see him make a home for himself and start what he refers to as “nesting” once they move into the newly discovered Men of Letters bunker. While Dean in earlier seasons reacted to being hit on by gay men with an awkward “Yeah, I don’t bat for your team,” the last man to try moves on Dean Winchester… kind of flattered him. In fact, he seemed put out that the guy had been lying to him to get information. Spending his nights in bars trying to pick up ladies holds less appeal than it did before. He’s still not a fan of salads, but he knows it’s good to eat one once in a while. In short, his priorities have clearly shifted; he’s an adult. He’s still gruff, still capable, still tougher than titanium, but no longer feels the need to project socially-typified masculine cues to prove himself. He’s more comfortable in his own skin.

Supernatural, Dean Winchester, Sam

In short, he’s a great role model for anyone concerned about what it means to “behave like a man.” Because Dean Winchester proves that there are no boundaries to that definition, and does it by carefully deconstructing every damaging stereotype that Hollywood still loves to lay on thick. He’s got that Steve McQueen swagger, that Paul Newman charm, that John Wayne no-nonsense… but he’s also a loving, nerdy, dedicated, annoying mass of insecurities and hopes. Because he’s a human being, and that’s how we roll.

So season nine can bring it on this fall. Supernatural has kept their family together by keeping fans rooting for their wayward brothers. And with development like the kind Dean Winchester has seen, it’s hardly surprising that we do.

Emily Asher-Perrin also has Steve McQueen swagger. You can bug her on Twitter and read more of her work here and elsewhere.


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