Dean Winchester (Supernatural)
Title: Protect and Survive
Author: marinarusalka
Character: Dean Winchester
Fandom:Supernatural
Spoilers: The entire series so far -- one full season
Big thanks to innie_darling and researchgrrrl for their help and advice in making this essay coherent.
Bio of a Hunter
"Take your brother outside as fast as you can, don't look back. Now, Dean, go!" -- John Winchester, Supernatural pilot.
"Here's the thing, when we were young, I pretty much pulled him from a fire. And ever since then, I've felt responsible for him, like it's my job to keep him safe." -- Dean, The Benders
The pilot episode of Supernatural opens with what is probably the most important formative experience of Dean Winchester's life. It is November 2, 1983. The Winchesters -- parents John and Mary, toddler Dean and baby Sam -- are a perfectly nice, normal middle-American family living in Lawrence, Kansas until some unknown demonic entity comes into their house, pins Mary to the nursery ceiling above Sam's crib, slashes her abdomen open and sets her on fire. As their life collapses around them, John orders Dean to carry Sam out of the burning house, making Dean responsible for his brother's life. Dean is four years old at the time.
Mary's death changes the Winchesters' lives forever. John, an ex-Marine, becomes determined to avenge his wife, an obsession that consumes him through the present day. He begins to hunt and kill every supernatural creature he can track down in the hope that eventually, one of the trails will lead him to Mary's killer. He raises his sons to do the same, training them in weapons and combat skills from early childhood.
A series of flashbacks in "Something Wicked" provides a glimpse of what this upbringing was like for Dean. John goes off on a hunt, leaving a nine-year-old Dean and a five-year-old Sam in a motel room with a loaded shotgun and orders for Dean to stay put, protect his brother, and shoot anyone who tries to come in. After several days of being trapped in the room, Dean loses his patience and sneaks out to play a video game. He returns to the motel just in time to see Sam get attacked by the monster his father's been hunting -- a shape-changing creature that feeds on the souls of children. John arrives in time to save Sam, but the creature gets away. As a result, Dean holds himself responsible not only for his brother's close call, but for all the other children subsequently attacked by the creature. Never again will he lightly disobey an order from his father.
By embracing the "family business" of evil-hunting and becoming his father's second in command, Dean makes it possible for Sam to longer retain his status as the protected, more "normal" member of the family. There are occasional mentions of Sam as a child doing things that most children do -- trying to join a soccer team, acting in a high school play. No such mentions ever come up in relation to Dean. As a result, Sam's character develops very differently from Dean's. As Sam gets older, he rebels against his father's authority and the pressure to devote his life to hunting. The conflict escalates, culminating in a fight when Sam announces he's going to Stanford on a scholarship and John tells him to go and stay gone. Sam goes, and breaks off all contact with his father. The canon timeline gets kind of messed up here, so it's not clear exactly how long Sam stays away and at what point he stopped talking to Dean too, but at the time of the pilot the brothers haven't spoken for at least two years. Dean stays behind to continue hunting with his father until John disappears during a hunt in California (Dean isn't there at the time, being away on a solo hunt in New Orleans).
Dean goes to Stanford to enlist his brother's aid in looking for John. Sam reluctantly goes along for one weekend, making it clear that he intends to remain in school. But when he does return, his girlfriend Jessica is murdered just as Mary was, giving Sam his own reason to seek revenge. At the end of the pilot, Dean and Sam take off together in Dean's '67 Chevy Impala to search for their father.
Family Ties
Dean: I can't do this alone.
Sam: Sure you can.
Dean: Yeah, well, I don't want to. -- Pilot
Being raised by a vengeance-obsessed demon hunter is not conducive to developing good people skills and Dean, on the whole, seems to do a better job communing with guns and cars than with other people. He's good at light-hearted banter, one-night stands, casual lies; not so good when it comes to any sort of honest exchange or genuine emotional connection -- unless small children are involved. In "Route 666" we find out that he was once involved in a romantic relationship with Cassie Robinson, which Cassie broke off after Dean told her what he did and she didn't believe him. Aside from this, Dean has no close canonical relationships with anyone other than his father and brother. As a result, his family is of paramount importance to him, and his vision of a happy life consists of himself, Sam and John all living and working together as one tight-knit, evil-hunting family.
Unfortunately for Dean, it's a dream that stands almost no chance of ever becoming reality. The timing of Mary's murder serves to differentiate Dean from both his brother and his father in important ways. Unlike Sam, he was old enough to remember his mother's death and the loss of an ordinary, happy childhood. Unlike John, he was too young to develop a lifelong obsession. Sam had no interest in hunting either as a quest or as a duty -- until Jessica's death drove him to share John's desire for revenge. Now both Sam and John are hunting for vengeance, and neither one of them has expressed any interest in continuing to hunt down random ghosts and monsters once the demon that killed Mary and Jessica is dead. Dean, on the other hand, sees hunting as a lifetime calling and a duty. When presenting his reasons for doing what he does (usually during arguments with Sam), he always brings up the fact that he's helping people and saving lives, but almost never mentions revenge. The image of himself as a hero and protector is as central to Dean's sense of identity as family loyalty, and both are closely intertwined in his mind. At the same time, he's very uncomfortable with the idea of other people viewing him as a hero. When the people he rescued attempt to thank him, his response is usually to look awkward and say something obnoxious.
In "Shadow," when Sam reiterates his desire to eventually quit hunting and return to college, Dean is hurt and upset. When Sam asks him what he wants for himself once the hunt for the demon is over, Dean responds with "It's never gonna be over. There's gonna be others. There's always gonna be something to hunt." In a rare display of emotional honesty, he admits that the main reason he dragged Sam away from Stanford when John disappeared was the hope that once John was found, they could all "be a family again." He's unable to accept, or even understand, Sam's response that they would still be a family even if they weren't all hunting together.
This fundamental disagreement over what life and family should be is a consistent source of conflict in Dean's relationship with Sam. Dean loves his brother. He's fiercely protective of him, wants him to be happy, but he doesn't understand Sam. Having chosen not to pursue the dream of a "normal life" for himself, Dean feels betrayed by Sam's insistence on clinging to it. Having accepted his father as the central authority figure in his life, he is puzzled by Sam's refusal to "be a good soldier" and follow John's instructions. He repeatedly accuses Sam of being selfish and disloyal. In "Scarecrow," an argument over Sam's unwillingness to follow an order from John actually leads the brothers to go their separate ways for a while. However, in a subsequent phone conversation, Dean says he's proud of Sam for going after what he wants and standing up to their father.
In "Skin," a shapeshifter takes on Dean's appearance and also "downloads" some of his thoughts and memories through a telepathic link. Talking to a captive Sam, the shapeshifter says, "He’s sure got issues with you. You got to go to college, he had to stay home. I mean, I had to stay home. With Dad. You don’t think I had dreams of my own? But Dad needed me. Where the hell were you?... See, deep down, I’m just jealous. You got friends, you could have a life. Me? I know I’m a freak. And sooner or later, everybody’s gonna leave me." The shapeshifter is evil, of course, and choosing its words to suit its purposes, but the episode strongly implies that the speech is a warped and exaggerated representation of Dean's real thoughts and feelings.
And yet, when they're not arguing or hunting, Dean and Sam interact as brothers who not only love but also genuinely like each other. Dean provides steady, unobtrusive emotional support while Sam grieves for Jessica during the early episodes of the season. Despite his stated hatred of "chick-flick" moments, he makes it clear that he's willing to listen if Sam wants to talk. As the season goes on and Sam recovers, there's a lot of snarky brotherly banter and horseplay. Dean and Sam often speak in unison without meaning to, finish each other's sentences, rapidly bounce ideas back and forth while discussing the background of a case. In "Hell House," they spend most of the episode gleefully playing silly practical jokes on each other. In "Provenance," Dean goes out of his way to encourage Sam to pursue a possible romance with a woman Sam clearly likes. He even offers to stay in town for a while after their job is completed, which for Dean is a fairly major concession. Throughout the season, the brothers never fully stop bickering, yet the love and loyalty between them always shines through.
Sam: So what, we gotta always follow Dad's orders?
Dean: Of course we do. -- Asylum
Sam: I don't understand the blind faith you have in the man. I mean, it's like you don't even question him.
Dean: Yeah, it's called being a good son. -- Scarecrow
Dean's relationship with his father, while not as argumentative as his relationship with Sam, is still difficult and complicated. Speaking to Sam in "Dead Man's Blood," John admits that he behaved more like a drill sergeant than a father in bringing up his children, something that the show strongly hinted at long before it was explicitly acknowledged. As the older, more obedient child, Dean experienced the greater share of John's boot-camp approach to child-raising. The flashbacks in "Something Wicked" indicate that Dean was given a great deal of adult responsibility at a very young age. The effort of living up to that responsibility largely shaped his character and his relationship with John. Dean couldn't afford to develop Sam's rebellious streak, and he internalized John's lessons of duty and military discipline in a way that Sam never did.
At the beginning of "Asylum," when John anonymously texts a set of coordinates to Dean's phone, Dean instantly interprets it as an order to go wherever the coordinates point and hunt whatever's there to hunt. His instinctive reaction is to follow the order, while Sam is both unconvinced that the orders come from John and disinclined to obey them if they do. Later in the episode, as the brothers investigate a haunted insane asylum, they continue to bicker over what Sam sees as Dean's excessive obedience to John. When Sam is attacked by a spirit that magnifies his existing feelings of anger and resentment, he accuses Dean of being his father's "good little soldier," of being desperate for John's approval and unable to think for himself.
It's true that in his interactions with John, Dean often acts more like a soldier toward a commander than a son toward a father. However, good soldiers are neither blind nor mindless, and neither is Dean. Yes, he follows John's orders, but that obedience is driven by a genuine respect for John's authority and proven hunting expertise (and also, admittedly, by Dean's overdeveloped sense of responsibility and fear of endangering others through his own failure). Yes, he habitually addresses John as "sir," but so does the super-rebellious Sam. And when all three Winchesters are finally reunited in person in "Shadow," John and Dean immediately move toward each other and embrace, while John and Sam circle each other like wary cats for some time before finally stepping into a hug.
The family reunion in "Shadow" is abruptly terminated by a demon attack. It's not until "Dead Man's Blood" that we see the Winchesters interact for an extended period of time, which gives the audience a picture of what the family dynamic must've been like before Sam left for Stanford. Sam and John are quickly at each other's throats, shoving and yelling and flinging accusations until Dean (who's been anticipating the argument since practically the moment John showed up) steps between them to restore peace. Dean doesn't overtly take sides, but impartially orders both Sam and John to simmer down and behave -- which they instantly do. Neither Sam nor John look particularly surprised by Dean's intervention, and Dean himself acts like a man who's done this a million times before and is well and truly sick of it. It appears that Dean has had plenty of practice being the immovable object between the two irresistible forces of his father and brother.
On the other hand, when Dean explicitly disagrees with John and sides with Sam during a later argument, everyone looks surprised, including Dean himself. And in "Salvation," when Dean angrily confronts John about his previous failures to respond when his sons really needed him, John says he's not sure he likes Dean's "new tone." Yet in the first instance, John changes his mind about pursuing the demon alone, and in the second instance he acknowledges that Dean is right and apologizes. So while John may be accustomed to having Dean fall in line behind him, he also respects Dean enough to pay attention when the expected obedience doesn't materialize.
"Sam, look. The three of us... it's all we have. It's all I have. Sometimes I feel like I'm barely holding it together, man." -- Dean, Salvation
Dean's most vulnerable and emotionally raw moments happen in the last two episodes of the season, as he comes to realize that both Sam and John are willing to sacrifice their lives to bring down the demon. In "Salvation," he says that if finding the demon leads to Sam's death then he'd rather never find it at all. In "Devil's Trap," he accuses Sam (and, by implication, John) of being selfish in their willingness to die for revenge. "I'm the one who'll have to bury you!" he rages. However problematic Dean's relationship with his family might be, it's abundantly clear that his father and brother are the most important people in his life.
Rebel, Rebel
Dean: Look, it sucks but…in a job like this, you can’t get close to people, period.
Sam:You’re kinda anti-social, you know that? -- Skin
The first Supernatural episode I ever saw was "Dead in the Water." At the time, I knew nothing about the show, the characters, the backstory or the actors, so I watched with no preconceptions. What I saw was an indecently gorgeous young man in frayed jeans and leather coat bonding, awkwardly but sincerely, with a frightened small boy. It could've easily come across as sappy, except for the utter lack of sappiness in Jensen Ackles's performance, and also for the fact that Dean's sincere moments were mixed with snarking at his brother, spouting really lame pick-up lines at the boy's mother, and brazenly impersonating a Federal Wildlife Service agent. This combination of gruff kindness and smart-alecky obnoxiousness pretty much sums up Dean's personality when dealing with the world outside his immediate family.
Dean's public persona is carefully constructed, but not always successful. He has a great deal of natural charisma, but not a lot by way of learned social skills, and it's always a toss-up whether he'll charm the pants off whomever he's talking to or just creep the hell out of them. He's perfectly believable while impersonating a police officer in "The Benders," but embarrassingly unconvincing dressed up as a priest in "Nightmare." He can bluff his way through any number of cover stories, but his attempt to warn off a couple of potential sacrifice victims in "Scarecrow" fails miserably, and Dean is left ruefully wishing that Sam was there to persuade the civilians with his "puppy-dog look." He carries himself with swaggering confidence until somebody challenges his lies or fails to be impressed by his manner, (like Missouri Moseley in "Home" or the Native American elder in "Bugs"), and then he quickly deflates.
When he's not hunting, Dean seems to spend most of his time and energy going through the motions of the sort of adolescent rebellion he couldn't actually afford to have as an adolescent. He wears a leather jacket, roars around the highways in a black muscle car, blasts head-banger music, flirts crudely with every half-way attractive woman he meets, and mouths off to cops and other authority figures. I suspect that the only reason he doesn't ride a motorcycle is that he needs a trunk to keep the guns in.
A lot of this behavior comes from a conscious rejection of the "normal life" his brother is so anxious to embrace. Dean is well aware that by the standards of conventional society he's trash -- a scruffy unemployed drifter whose worldly belongings all fit into the trunk of his car -- and he chooses to embrace his outsider status. He cheerfully refers to himself as "a freak" and claims he'd rather kill himself than live in a nice house with a white picket fence. "I'll take our family over normal any day," he says in "Bugs." How much of this is genuine and how much is a defense mechanism? Ask ten people in the fandom, and you're likely to get eleven different answers.
This tension between appearance and reality lies at the heart of Dean's appeal for me. I've always been fascinated by characters who wear masks, who hide their emotional layers beneath layers of stoicism or snarky humor (or, ideally, both), characters who make me work to figure out who they are, and who then reward my work by revealing genuine depth and complexity. And my first season of compulsively analyzing Dean Winchester has certainly been a rewarding experience.
Links
These are only a small sampling of what's available. Supernatural fandom is growing rapidly, and new communities and websites spring up every day. But the links below should keep any interested newbie occupied for a good long time.
Places to get started
Newbie guide to Supernatural
Supernatural overview at crack_van -- a little out of date now, but still useful
General show sites
Supernatural.tv
Official WB site
Jensen Ackles
Jensen Ackles Fans
Fanfic communities
supernaturalfic -- the largest of the fanfic communities, all genres and ratings
spn_gen
sn_slash -- mostly Wincest (Sam/Dean)
spn_het
spn_brotherlove -- no Wincest
Discussion and general show-related communities
supernatural_tv
sn_discussion
spn_heavymeta
spnnewsletter
Author: marinarusalka
Character: Dean Winchester
Fandom:Supernatural
Spoilers: The entire series so far -- one full season
Big thanks to innie_darling and researchgrrrl for their help and advice in making this essay coherent.
Bio of a Hunter
"Take your brother outside as fast as you can, don't look back. Now, Dean, go!" -- John Winchester, Supernatural pilot.
"Here's the thing, when we were young, I pretty much pulled him from a fire. And ever since then, I've felt responsible for him, like it's my job to keep him safe." -- Dean, The Benders
The pilot episode of Supernatural opens with what is probably the most important formative experience of Dean Winchester's life. It is November 2, 1983. The Winchesters -- parents John and Mary, toddler Dean and baby Sam -- are a perfectly nice, normal middle-American family living in Lawrence, Kansas until some unknown demonic entity comes into their house, pins Mary to the nursery ceiling above Sam's crib, slashes her abdomen open and sets her on fire. As their life collapses around them, John orders Dean to carry Sam out of the burning house, making Dean responsible for his brother's life. Dean is four years old at the time.
Mary's death changes the Winchesters' lives forever. John, an ex-Marine, becomes determined to avenge his wife, an obsession that consumes him through the present day. He begins to hunt and kill every supernatural creature he can track down in the hope that eventually, one of the trails will lead him to Mary's killer. He raises his sons to do the same, training them in weapons and combat skills from early childhood.
A series of flashbacks in "Something Wicked" provides a glimpse of what this upbringing was like for Dean. John goes off on a hunt, leaving a nine-year-old Dean and a five-year-old Sam in a motel room with a loaded shotgun and orders for Dean to stay put, protect his brother, and shoot anyone who tries to come in. After several days of being trapped in the room, Dean loses his patience and sneaks out to play a video game. He returns to the motel just in time to see Sam get attacked by the monster his father's been hunting -- a shape-changing creature that feeds on the souls of children. John arrives in time to save Sam, but the creature gets away. As a result, Dean holds himself responsible not only for his brother's close call, but for all the other children subsequently attacked by the creature. Never again will he lightly disobey an order from his father.
By embracing the "family business" of evil-hunting and becoming his father's second in command, Dean makes it possible for Sam to longer retain his status as the protected, more "normal" member of the family. There are occasional mentions of Sam as a child doing things that most children do -- trying to join a soccer team, acting in a high school play. No such mentions ever come up in relation to Dean. As a result, Sam's character develops very differently from Dean's. As Sam gets older, he rebels against his father's authority and the pressure to devote his life to hunting. The conflict escalates, culminating in a fight when Sam announces he's going to Stanford on a scholarship and John tells him to go and stay gone. Sam goes, and breaks off all contact with his father. The canon timeline gets kind of messed up here, so it's not clear exactly how long Sam stays away and at what point he stopped talking to Dean too, but at the time of the pilot the brothers haven't spoken for at least two years. Dean stays behind to continue hunting with his father until John disappears during a hunt in California (Dean isn't there at the time, being away on a solo hunt in New Orleans).
Dean goes to Stanford to enlist his brother's aid in looking for John. Sam reluctantly goes along for one weekend, making it clear that he intends to remain in school. But when he does return, his girlfriend Jessica is murdered just as Mary was, giving Sam his own reason to seek revenge. At the end of the pilot, Dean and Sam take off together in Dean's '67 Chevy Impala to search for their father.
Family Ties
Dean: I can't do this alone.
Sam: Sure you can.
Dean: Yeah, well, I don't want to. -- Pilot
Being raised by a vengeance-obsessed demon hunter is not conducive to developing good people skills and Dean, on the whole, seems to do a better job communing with guns and cars than with other people. He's good at light-hearted banter, one-night stands, casual lies; not so good when it comes to any sort of honest exchange or genuine emotional connection -- unless small children are involved. In "Route 666" we find out that he was once involved in a romantic relationship with Cassie Robinson, which Cassie broke off after Dean told her what he did and she didn't believe him. Aside from this, Dean has no close canonical relationships with anyone other than his father and brother. As a result, his family is of paramount importance to him, and his vision of a happy life consists of himself, Sam and John all living and working together as one tight-knit, evil-hunting family.
Unfortunately for Dean, it's a dream that stands almost no chance of ever becoming reality. The timing of Mary's murder serves to differentiate Dean from both his brother and his father in important ways. Unlike Sam, he was old enough to remember his mother's death and the loss of an ordinary, happy childhood. Unlike John, he was too young to develop a lifelong obsession. Sam had no interest in hunting either as a quest or as a duty -- until Jessica's death drove him to share John's desire for revenge. Now both Sam and John are hunting for vengeance, and neither one of them has expressed any interest in continuing to hunt down random ghosts and monsters once the demon that killed Mary and Jessica is dead. Dean, on the other hand, sees hunting as a lifetime calling and a duty. When presenting his reasons for doing what he does (usually during arguments with Sam), he always brings up the fact that he's helping people and saving lives, but almost never mentions revenge. The image of himself as a hero and protector is as central to Dean's sense of identity as family loyalty, and both are closely intertwined in his mind. At the same time, he's very uncomfortable with the idea of other people viewing him as a hero. When the people he rescued attempt to thank him, his response is usually to look awkward and say something obnoxious.
In "Shadow," when Sam reiterates his desire to eventually quit hunting and return to college, Dean is hurt and upset. When Sam asks him what he wants for himself once the hunt for the demon is over, Dean responds with "It's never gonna be over. There's gonna be others. There's always gonna be something to hunt." In a rare display of emotional honesty, he admits that the main reason he dragged Sam away from Stanford when John disappeared was the hope that once John was found, they could all "be a family again." He's unable to accept, or even understand, Sam's response that they would still be a family even if they weren't all hunting together.
This fundamental disagreement over what life and family should be is a consistent source of conflict in Dean's relationship with Sam. Dean loves his brother. He's fiercely protective of him, wants him to be happy, but he doesn't understand Sam. Having chosen not to pursue the dream of a "normal life" for himself, Dean feels betrayed by Sam's insistence on clinging to it. Having accepted his father as the central authority figure in his life, he is puzzled by Sam's refusal to "be a good soldier" and follow John's instructions. He repeatedly accuses Sam of being selfish and disloyal. In "Scarecrow," an argument over Sam's unwillingness to follow an order from John actually leads the brothers to go their separate ways for a while. However, in a subsequent phone conversation, Dean says he's proud of Sam for going after what he wants and standing up to their father.
In "Skin," a shapeshifter takes on Dean's appearance and also "downloads" some of his thoughts and memories through a telepathic link. Talking to a captive Sam, the shapeshifter says, "He’s sure got issues with you. You got to go to college, he had to stay home. I mean, I had to stay home. With Dad. You don’t think I had dreams of my own? But Dad needed me. Where the hell were you?... See, deep down, I’m just jealous. You got friends, you could have a life. Me? I know I’m a freak. And sooner or later, everybody’s gonna leave me." The shapeshifter is evil, of course, and choosing its words to suit its purposes, but the episode strongly implies that the speech is a warped and exaggerated representation of Dean's real thoughts and feelings.
And yet, when they're not arguing or hunting, Dean and Sam interact as brothers who not only love but also genuinely like each other. Dean provides steady, unobtrusive emotional support while Sam grieves for Jessica during the early episodes of the season. Despite his stated hatred of "chick-flick" moments, he makes it clear that he's willing to listen if Sam wants to talk. As the season goes on and Sam recovers, there's a lot of snarky brotherly banter and horseplay. Dean and Sam often speak in unison without meaning to, finish each other's sentences, rapidly bounce ideas back and forth while discussing the background of a case. In "Hell House," they spend most of the episode gleefully playing silly practical jokes on each other. In "Provenance," Dean goes out of his way to encourage Sam to pursue a possible romance with a woman Sam clearly likes. He even offers to stay in town for a while after their job is completed, which for Dean is a fairly major concession. Throughout the season, the brothers never fully stop bickering, yet the love and loyalty between them always shines through.
Sam: So what, we gotta always follow Dad's orders?
Dean: Of course we do. -- Asylum
Sam: I don't understand the blind faith you have in the man. I mean, it's like you don't even question him.
Dean: Yeah, it's called being a good son. -- Scarecrow
Dean's relationship with his father, while not as argumentative as his relationship with Sam, is still difficult and complicated. Speaking to Sam in "Dead Man's Blood," John admits that he behaved more like a drill sergeant than a father in bringing up his children, something that the show strongly hinted at long before it was explicitly acknowledged. As the older, more obedient child, Dean experienced the greater share of John's boot-camp approach to child-raising. The flashbacks in "Something Wicked" indicate that Dean was given a great deal of adult responsibility at a very young age. The effort of living up to that responsibility largely shaped his character and his relationship with John. Dean couldn't afford to develop Sam's rebellious streak, and he internalized John's lessons of duty and military discipline in a way that Sam never did.
At the beginning of "Asylum," when John anonymously texts a set of coordinates to Dean's phone, Dean instantly interprets it as an order to go wherever the coordinates point and hunt whatever's there to hunt. His instinctive reaction is to follow the order, while Sam is both unconvinced that the orders come from John and disinclined to obey them if they do. Later in the episode, as the brothers investigate a haunted insane asylum, they continue to bicker over what Sam sees as Dean's excessive obedience to John. When Sam is attacked by a spirit that magnifies his existing feelings of anger and resentment, he accuses Dean of being his father's "good little soldier," of being desperate for John's approval and unable to think for himself.
It's true that in his interactions with John, Dean often acts more like a soldier toward a commander than a son toward a father. However, good soldiers are neither blind nor mindless, and neither is Dean. Yes, he follows John's orders, but that obedience is driven by a genuine respect for John's authority and proven hunting expertise (and also, admittedly, by Dean's overdeveloped sense of responsibility and fear of endangering others through his own failure). Yes, he habitually addresses John as "sir," but so does the super-rebellious Sam. And when all three Winchesters are finally reunited in person in "Shadow," John and Dean immediately move toward each other and embrace, while John and Sam circle each other like wary cats for some time before finally stepping into a hug.
The family reunion in "Shadow" is abruptly terminated by a demon attack. It's not until "Dead Man's Blood" that we see the Winchesters interact for an extended period of time, which gives the audience a picture of what the family dynamic must've been like before Sam left for Stanford. Sam and John are quickly at each other's throats, shoving and yelling and flinging accusations until Dean (who's been anticipating the argument since practically the moment John showed up) steps between them to restore peace. Dean doesn't overtly take sides, but impartially orders both Sam and John to simmer down and behave -- which they instantly do. Neither Sam nor John look particularly surprised by Dean's intervention, and Dean himself acts like a man who's done this a million times before and is well and truly sick of it. It appears that Dean has had plenty of practice being the immovable object between the two irresistible forces of his father and brother.
On the other hand, when Dean explicitly disagrees with John and sides with Sam during a later argument, everyone looks surprised, including Dean himself. And in "Salvation," when Dean angrily confronts John about his previous failures to respond when his sons really needed him, John says he's not sure he likes Dean's "new tone." Yet in the first instance, John changes his mind about pursuing the demon alone, and in the second instance he acknowledges that Dean is right and apologizes. So while John may be accustomed to having Dean fall in line behind him, he also respects Dean enough to pay attention when the expected obedience doesn't materialize.
"Sam, look. The three of us... it's all we have. It's all I have. Sometimes I feel like I'm barely holding it together, man." -- Dean, Salvation
Dean's most vulnerable and emotionally raw moments happen in the last two episodes of the season, as he comes to realize that both Sam and John are willing to sacrifice their lives to bring down the demon. In "Salvation," he says that if finding the demon leads to Sam's death then he'd rather never find it at all. In "Devil's Trap," he accuses Sam (and, by implication, John) of being selfish in their willingness to die for revenge. "I'm the one who'll have to bury you!" he rages. However problematic Dean's relationship with his family might be, it's abundantly clear that his father and brother are the most important people in his life.
Rebel, Rebel
Dean: Look, it sucks but…in a job like this, you can’t get close to people, period.
Sam:You’re kinda anti-social, you know that? -- Skin
The first Supernatural episode I ever saw was "Dead in the Water." At the time, I knew nothing about the show, the characters, the backstory or the actors, so I watched with no preconceptions. What I saw was an indecently gorgeous young man in frayed jeans and leather coat bonding, awkwardly but sincerely, with a frightened small boy. It could've easily come across as sappy, except for the utter lack of sappiness in Jensen Ackles's performance, and also for the fact that Dean's sincere moments were mixed with snarking at his brother, spouting really lame pick-up lines at the boy's mother, and brazenly impersonating a Federal Wildlife Service agent. This combination of gruff kindness and smart-alecky obnoxiousness pretty much sums up Dean's personality when dealing with the world outside his immediate family.
Dean's public persona is carefully constructed, but not always successful. He has a great deal of natural charisma, but not a lot by way of learned social skills, and it's always a toss-up whether he'll charm the pants off whomever he's talking to or just creep the hell out of them. He's perfectly believable while impersonating a police officer in "The Benders," but embarrassingly unconvincing dressed up as a priest in "Nightmare." He can bluff his way through any number of cover stories, but his attempt to warn off a couple of potential sacrifice victims in "Scarecrow" fails miserably, and Dean is left ruefully wishing that Sam was there to persuade the civilians with his "puppy-dog look." He carries himself with swaggering confidence until somebody challenges his lies or fails to be impressed by his manner, (like Missouri Moseley in "Home" or the Native American elder in "Bugs"), and then he quickly deflates.
When he's not hunting, Dean seems to spend most of his time and energy going through the motions of the sort of adolescent rebellion he couldn't actually afford to have as an adolescent. He wears a leather jacket, roars around the highways in a black muscle car, blasts head-banger music, flirts crudely with every half-way attractive woman he meets, and mouths off to cops and other authority figures. I suspect that the only reason he doesn't ride a motorcycle is that he needs a trunk to keep the guns in.
A lot of this behavior comes from a conscious rejection of the "normal life" his brother is so anxious to embrace. Dean is well aware that by the standards of conventional society he's trash -- a scruffy unemployed drifter whose worldly belongings all fit into the trunk of his car -- and he chooses to embrace his outsider status. He cheerfully refers to himself as "a freak" and claims he'd rather kill himself than live in a nice house with a white picket fence. "I'll take our family over normal any day," he says in "Bugs." How much of this is genuine and how much is a defense mechanism? Ask ten people in the fandom, and you're likely to get eleven different answers.
This tension between appearance and reality lies at the heart of Dean's appeal for me. I've always been fascinated by characters who wear masks, who hide their emotional layers beneath layers of stoicism or snarky humor (or, ideally, both), characters who make me work to figure out who they are, and who then reward my work by revealing genuine depth and complexity. And my first season of compulsively analyzing Dean Winchester has certainly been a rewarding experience.
Links
These are only a small sampling of what's available. Supernatural fandom is growing rapidly, and new communities and websites spring up every day. But the links below should keep any interested newbie occupied for a good long time.
Places to get started
Newbie guide to Supernatural
Supernatural overview at crack_van -- a little out of date now, but still useful
General show sites
Supernatural.tv
Official WB site
Jensen Ackles
Jensen Ackles Fans
Fanfic communities
supernaturalfic -- the largest of the fanfic communities, all genres and ratings
spn_gen
sn_slash -- mostly Wincest (Sam/Dean)
spn_het
spn_brotherlove -- no Wincest
Discussion and general show-related communities
supernatural_tv
sn_discussion
spn_heavymeta
spnnewsletter