Supernatural is one of the most amazing TV shows to be developed in a long time, and Dean Winchester is one of its amazing characters. He is a three dimensional, dynamic, realistic person brought to life by the incredible team of writers on the series and the extraordinary acting of Jensen Ackles. Jensen’s intense acting range and the depth of his talent gives him the subtlety to depict the complex and multilayered character of Dean Winchester with honesty and empathy, allowing us to feel Dean's pain, anger and happiness. I believe the writers and Jensen have done as awesome job of presenting, developing and nurturing the character, and believe in giving praise and credit where it is due. The best writers in the world can create the best character in the world, but if they don’t have an extremely adept actor to play the part, their character will never come to life. And the opposite is true as well. No matter how talented the actor, a poorly written script will give a writer a mediocre character at best. We have been fortunate to be blessed with both on Supernatural
There are many layers of Dean Winchester’s complicated personality. His actions are believable and understandable, a character many Supernatural fans can relate to very easily. Some simplify his character to that of being his brother’s keeper, but to do that not only takes away from both characters, but also from the richness of the story being told.
Dean Winchester is flawed and that makes him perfect. His flaws are many, and he readily admits to all of them. He is determined and devoted to his brother, to his job of hunting (unless it jeopardizes Sam’s life), and to the few people he loves. He is clever, quick, imaginative, and definitely able to think on his feet. He is obnoxious, forward, close-minded, and stubborn, but is also extremely valiant, fiercely protective, compassionate and loyal. He is extremely committed, and believes more in the present than in the past. He doesn’t strive for perfection, and can be both incredibly selfless and selfish (particularly when it comes to Sam) almost simultaneously. (All Hell Breaks Loose Part II, 2.22). He does what needs to be done because there's no one else to do it. He helps humanity because it’s the right thing to do, because they need help, and not because of some reward he’ll receive here, or in the afterlife.
His family always came first with him and he was willing to forego whatever dreams or aspirations he had to hold his family together, to protect Sam and to support John. Portrayed very aptly in What is and What Should Never Be (2.20), even though he gets his wish, a chance at a normal life for him and Sam, he can’t relinquish the task of hunting.....of being the righteous man. He was even willing to give up finding Azazel in order to keep Sam alive (Salvation, 1.21). He is the one who never lost sight of the fact that family came first, vengeance second. He can be vengeful, but, for him, revenge has its limits. 
As the first born of John, he spent his entire life being the strong one, the anchor, not only for his younger brother, but for his father as well (In My Time of Dying, 2.01). His early years were spent in the warmth and love of a very devoted father and mother, giving Dean an unwavering concept of compassion, of sensitivity, of right and wrong, and of devotion to family, all gifts from Dad that he has used to shape his personality. His trials and tribulations made him stronger, not weaker, which make him more of a hero than most who claim to be.
With the death of his mother his father placed a great deal of responsibility on him. It was necessary for him to grow up very fast, a path he chose to accept, a path many would have abandoned. He grew up in a world where monsters were real, and children really did have to check under beds at night. But with his fiercely protective nature for Sam, he shielded Sam from these aspects of the world, at least for a little while….much longer than Dean ever had, and not because he was told to, but because he wanted to. He wanted Sam to have the childhood he never had.    
Left alone when dad went on hunts, Dean was forced to find a way of dealing with his fears. He had to find ways of reassuring himself that dad was going to return alive, and not succumb to the terror that his father might never come back, a burden he could not share with anyone, especially Sam. He always put on a brave front for his younger brother and made light of things so that Sam wouldn't worry. And he did so in his own glib, smartass way as a way of concealing his own pain and loneliness, but that was only for others, it never fooled Sam. He created the superhero persona of John Winchester because to contemplate the fact that his father was only human would allow his fears to take precedence. And he couldn’t afford to be afraid, to give into the basic anxiety of being abandoned and isolated in a hostile world. This forced him to develop survival skills and allowed his leadership talents to be sharpened, compensating for the lack of a secure, trusting, and loving environment normal children had.  
He was loyal to Sam and obedient to John, but he was not opposed to stepping in and telling both Dad and Sam to “back off” when mediating fights between them (Dead Man’s Blood, 1.20). He takes pleasure in the simple things; food (especially bacon cheese burgers, and no I don’t think he has given them up), alcohol, sex (need I mention vibrating beds), music, his car, and ‘killing some evil sons of bitches’. (And if that’s all he asks from us, I’d say we got the better of the deal!)
Though he enjoys being around people, particularly women, it is extremely difficult for him to open up with anyone. He is very introverted when it comes to sharing intimate details about himself, and is afraid of becoming attached, as the few people he bonded to, left him in one way or another.  Never wanting to appear vulnerable to Sam, he will only share his feelings with him when he is pushed or reaches an obvious breaking point (Heaven and Hell, 3.10). In reality the only thing he ever wanted is a family, and that’s the one thing he can never have. Dean is in constant conflict between having relationships, which require him to open up, and being alone because he is afraid to open up.
His decision to sell his soul for Sam is a natural one. He made a conscience choice to go to hell and he knew that was far more dangerous than dying. For most of us dying means a release from pain, sorrow and grief….of going to a better place. Not so in the boy’s world. Going to hell was not the end of pain and grief, but only the beginning, especially for a Winchester (Sin City, 3.04).   Many have speculated that Dean sold his soul partly because he couldn’t stand the thought of being alone, and partly because he felt a sense of failure, a low self-worth from all the years of protecting Sam. Because he was supposed to be dead, twice over, and both times someone lost their life because of him (Faith, 1,12, In My Time of Dying, 2.01), it’s guilt that also motivated him to sacrifice himself for Sam. Maybe so… or maybe he was just simply like his Dad. John couldn’t live with the death of Dean, and Dean couldn’t live with death of Sam. No parent should watch an offspring die, and no sibling should watch another sibling die. How many of us have experienced the same feelings? How many of us wouldn’t have done the same thing in that situation? And I don’t think we are all insecure, have low esteem, and consider ourselves failures.   I think Dean just did what anyone would, and as this is the Winchester world, both John and Dean knew how to stop the pain and choose to take that course, fully aware of the consequences.   (After all, Dean is John’s son.) Given the option, would he do the same thing again?…yeah, he would, so would John…after all to them that’s what family is all about.  
Having only a year to live forced Dean to realize that even though he loved his Dad, John was far from perfect. That his childhood left a lot to be desired, and was no fault of his own, a fact he is still coming to grips with today. It’s only due to his strength, strong will, and his ability to adapt that he was capable of functioning at all.  It is clear that Dean himself came to understand the ramifications of growing up in the kind of environment he did, having to shoulder responsibilities that are hard enough for a grown man to handle, let alone a child. He alludes to his bitterness about the lack of attention his father showed him. In No Exit, (2.6) he tells Jo, “You’ve got a mother that worries about you, who wants something more for you. Those are good things. You don’t throw things like that away. Might be hard to find later”.  Dean even calls his father “an ass” for telling him he might have to kill Sam, saying that “you don’t lay that kind of crap on your kids” (Playthings, 2.11). None of this alters the fact that Dean idolizes his father to this day and good or bad, its part of the traits that make up his personality. After all, he would have experience a very loving devoted dad during the first 4 years of his life. And memories formed in those years, are deeply rooted in your persona and will stay with you all the rest of your life. Memories of a dad, Sam never saw.
Dean had been told that his humanity would burn away in hell, but his loss of love only took 30 years (Hell time that is….now THAT’S something I never thought I would say!). A large burden to bear after he found out his father never lost his, even after 100 (On The Head of a Pin, 4.16).  Dean was not to blame for his downfall, he was lost and alone, a fate to Dean that was worse than any physical pain could ever be. Dean’s high need for affiliation, acceptance, love, and appreciation from his family requires maintaining closeness largely based on physical proximity. He was alone, John wasn’t there, Sam wasn’t there, and even though he could justify why Sam never came for him, subconsciously he always counted greatly on his brother help, as he had all his life. But after 30 years, he did what Dean does best…. he adapted to his situation. (After all, he’s also his mother’s son.) He coped the only way he could…he choose…he choose to lose a battle but not the war…though his trip back to the battle will be a long and hard one. But as Sera Gamble said, “that’s what makes ‘em heroes.”
His choice earned him redemption, and from what we’ve seen, it was apparently his only way out. If he hadn’t gotten back to Sammy, Ruby would be alive, little brother will be Lucifer’s meat suit….and we would all be toast!
We are the sum of our experiences, and the more experiences we have the more we need to rely on the traits we were given. Dean personality, with all its faults and merits (yes, even his time in hell), have developed him into a well respected leader. He seeks to improve the world and those around him, to the benefit of all.   He readily challenges the status quo, rebels against authority, and has no problem standing up for what he believes in. He has the ability to influence people by example, logical argument, enthusiasm, and persistence. He never seeks to dominate others, just differentiate himself and make his position known. And he has the courage to speak out when needed. His upbringing, filled with insecurities, loneliness and fear, has ingrained in him the ability to choose. 
What I love most about Dean Winchester is that he is a survivor. Dean Winchester took the cards that were dealt him and played his hand the best way possible, in all situations he found himself. He made his choices and accepted responsibility for each one, always thinking of others before himself. He never gives up. He tenaciously chooses to shape his own fate, and as long as he refuses to give up free will, he will find what he is looking for. Family and humanity will always be his weakness, as that is the fate that befalls a righteous person, a burden that he will carry throughout his live. His devotion to his brother and humanity are equal, he will not sacrifice one for the other. He would “rather die” than kill his brother, and to Dean there is no point in having a world, if his brother isn’t in it. He has never wavered from his commitment, or his values of right and wrong, and I really can’t see him changing that now. 
So Dean will take his G.E.D, and his give ‘em Hell attitude, and show both heaven and hell that the smarter brother is back (Sin City, 3.04) . “Screw the angels and the demons and their crap apocalypse. If they want to fight a war, they can find their own planet. This one’s ours and I say they get the hell off it. We take them all on, we kill the Devil, hell we’ll kill Michael if we have to but we do it our own damn selves.”(Sympathy For The Devil, 5.01). And there is no question in my mind that he will do just that!. 
So am putting Dean Winchester on a pedestal…maybe so?   But maybe, that’s where I think he should be…