“My name is Dean Winchester. I’m an Aquarius, I enjoy sunsets, long walks on the beach, and women.”
Dean Winchester started out as a stereotypical ‘Han Solo’ character. As seasons go on, the audience gets an in-depth look at the complex character, who usually puts up a tough front.
Dean is a movie buff and a complete geek for things like Lord of the Rings, Startrek, and Disney. He’s afraid of snakes, gets squeamish around witchcraft, loves pie, and has never set foot on a beach. Dean, much like his fellow CW characters on The Vampire Diaries, is a cured vampire. He is also the only confirmed character to be able to see into the Fairy Realm.
As the big brother to Sam, he was often a parent. Cooking, cleaning, and managing the finances while John was off on a job. He spent his entire childhood training to be a hunter. His first hunt was before he was nine, he was never a child and had far more responsibility than most. “All he ever did was train you… boss you around. But Sam? Sam he doted on. Sam he loved. Dad knew who you really were… a good soldier and nothing else. Daddy’s blunt little instrument.” His attitude of putting Sam first has influenced every action Dean has made throughout life and is part of his lack of self-worth. “I don’t care what happens to me. I never really have. But I do care about what happens to my brother.”
25: FLY AWAY WITH ME
Dean spends much of his time pretending to be fearless. The truth is, despite going up against monsters and ghosts all his life he has a deep fear of flying. Sam was unaware of this fact until their first demon case and they need to go up on a plane, ready to crash. “It’s never really been an issue till now. Why do you think I drive everywhere Sam?!”
This particular flight only heightened his fear. The next time he went on a flight was to Scotland to bargain with Crowley, during which “he white-knuckled his way through four puke bags.” Only now, he’s also concerned about demonic influence: “Some nut job decided to try something. I was ready. I had a fork.”
24: GIDDY UP COWBOY
He is a huge cowboy fan. In Frontierland he has the opportunity to time travel back to 1861. Whilst this journey had some rude awakenings like the hygiene, law, and drink quality, it was still a wish-fulfillment moment for Dean when he became the sheriff of Sunrise, Wyoming. Sam claims that Dean is “obsessed” and “can recite every Clint Eastwood movie ever made, even the monkey movies.”
The second case was in Dodge City, Kansas. Dean put on his cowboy hat and forced one on Cas, getting Team Free Will set up in the “Wild Bill Suite.” The episode confirming cases of cowboy movie nights, forcing an angel to endure such classics as Tombstone: “the one with guns and tuberculosis.”
23: A LIFELONG MISSION
Dean was born January twenty-fourth, 1979 and became a hunter-in-training by the time he was four, when he lost his mother. His father John found his way to the hunters Missouri and Bobby, discovering the supernatural world. In a flashback with Sam’s Zanna, Sully, it’s confirmed that Dean went on his first hunting trip before he was nine, although he had faced monsters that came after Sam before that (Shtriga). Dean has only ever taken a year off hunting, so less than five years of his life were spent ‘normal.’ Despite his attempts to be normal his warrior upbringing wins out every time.
22: HE'S A LADIES MAN
In Afterschool Special the episode shows flashbacks of the boys’ time at Truman High in 1997. In this episode, Dean is portrayed as quite the ladies man. However, it soon becomes apparent that this story is more from Sam’s perspective, especially in the season nine episode: Bad Boys. Dean got done shoplifting Sam food and ended up in a boys home when he was sixteen. We discover Dean is actually awkward, learned a little guitar, wanted to be a rock star and had his first kiss with a girl called Robin while he was there. As the series goes on it’s easy to see that Dean isn’t quite as smooth as he and Sam think he is.
Dean has the monopoly on time travel in Supernatural, usually, this is thanks to angelic assistance, but in season seven Dean finds himself swallowed up by Cronus, the God of Time. He lands in 1944 Chicago and finds himself seated across the interrogation table with Elliot Ness.
Dean is a huge fan of Ness, and mentioned earning the title ‘Untouchable’ while he was there. “Untouchables is like one of my most favorite movies ever… I must’ve seen it like fifty times.” The movie is an adaptation of the takedown of Al Capone by Ness’ Prohibition enforcement team: The Untouchables. It isn’t until Dean is about to return home that Ness bestows the title, making Dean an honorary ‘Untouchable.’
20: BULLET NUMBER SIX
The Colt is a famous weapon made by tying its properties to a Devil’s Gate on the night of a comet, during The Battle of Alamo, able to vanquish all but five beings. When John explains the history of the Colt he says that Samuel Colt used “half a dozen bullets” out of the original thirteen (thought irreplaceable). Truthfully, Samuel only used five bullets and the sixth was used by Dean who went back in time to the fifth of March 1861 to destroy a Phoenix. Dean used three of the original thirteen.
In Clap Your Hands If You Believe the boys think they’re investigating an actual UFO case. After Dean, the first born, is abducted by the “grabby incandescent [jerks],” they can no longer hide from his sight. After Dean went up against Tinkerbell whilst listening to Space Oddity they had to acknowledge it wasn’t aliens at all, but fairies. Whilst he may not have been there long he did cross over into the “Fairy realm”/Avalon. It isn’t entirely clear what happened to Dean or the other first-born sons when they were beamed away, but it did leave Dean with a handy ability.
18:BEAM ME UP, SCOTTY
When Dean went to the Pit at the end of the third season fans were left reeling, no one believing it would actually happen. For four earth months, he was harmed at the hands of Alistair. What followed was the best change the series has seen in its long run with the introduction of angels and Castiel, who “raised [Dean] from perdition.” Angels almost seldom came to Earth in at least 2000 years; this makes Dean the first person to be raised from the underworld by an angel in that time. This not only left him marked by Heaven and the Pit, but given the time difference downstairs his consciousness is forty years older than his biological age.
Dean, whilst being “raised in the life,” still had moments of doubt. Particularly evident in Bad Boys when we see his younger self admit he dislikes hunting. In Bloodlust, Dean tells the hunter Gordon about the hunt that changed it all. He “picked up this crossbow and hit that ugly sucker.” While Sam waits in the car, he eliminates the body with his dad. He looked into that fire and Dean accepted his fate: “I’m sixteen years old. Kids my age are worried about pimples, prom dates. I’m seeing things that they’ll never even know, never even dream of. So right then, I just sort of… embraced the life.”
16:HE'S QUITE THE TECHY
Dean’s childhood was hardly normal, and his skill set is centered around hunting. “I was six or seven and he took me shooting for the first time… I bulls-eyed every one of ‘em.” While John kept Sam’s soccer trophy, Dean found his dad kept his weaponry: “It’s my first sawed-off. Made it myself. Sixth grade.”
When Sam was at Stanford, Dean made an EMF Detector out of his Walkman to detect electromagnetic waves given off by spiritual activity. And, in the season one episode Hook Man, the common hunter’s trick of rock salt in the shotgun is revealed to have actually been Dean’s idea.
Vanquishing demons were thought to be impossible by all hunters of John’s generation, the only exception being the mythological Colt. Dean was the first Winchester (and likely the first hunter since Colt) to destroy a demon. He was also the first hunter to take down a demon with Ruby’s knife (ancient demon knife of the Kurds), which he used to take down Ruby’s demon master, Astaroth. He was also the first person to ever eliminate a King/Prince of the Underworld (Azazel) and a Knight of the Underworld, Abbadon (Cain defeated the others, but was a demon at the time).
14: SOMETIMES HE FLIES SOLO
When Dean collects Sam from Stanford, the younger brother is surprised to find that Dean had been hunting alone. Dean hunted solo for years; he would have started at about twenty-two, starting sometime after Sam left for Stanford. The show mentions several cases Dean and John worked together (such as a poltergeist in Pennsylvania), but Dean was often on his own. A few solo jobs that were mentioned include the New Orleans voodoo case, two vatala, and the unknown monster that controlled Cole’s father. Very few hunters do jobs solo. It speaks to Dean’s ability that he managed on his own at such a young age.
Dean Winchester has met his end more than anyone on the show, and technically Dean has taken his own life five times. He made a demon deal, a doctor stopped his heart so he could negotiate with Demise and he took pills to talk to Billie (reaper). All in order to save the life of his brother.
He also bargained with Billie to take the boys’ lives in order for them to escape a black site with the intention that one of them would permanently ‘retire’ afterward. Lastly, in light of losing his mother and Cas, he gave himself an injection to the heart to go to the veil.
Dean is definitely the only cook in the Winchester clan. Without much money or instruction, or even a proper kitchen he would make sure Sam had dinner.
“My dad was always working so I came up with about 101 ways to make mac and cheese.” “Add ketchup for spice.” “Tuna, hotdogs, fluff marshmallow mix.” While they may not have been delicious his “brother thought it was exotic.” He was willing to make the best out little resources, often making truly bad meals, a trait he inherited from Mary. We soon realize that once Dean has access to an actual kitchen he enjoys cooking and is actually quite the chef.
In season four the difference between demons and angels is made very clear, even Lilith didn’t know how to destroy angels. Uriel claiming, “The only thing that can [end] an angel is another angel.”
However, this changes when Dean meets Zachariah, who he despises instantly. “Angel or not, I will stab you in your face.” Dean is a man of his word, because that is exactly what he did. This makes Dean quite possibly the first human (or demon) to ever vanquish an angel. Since then Dean has managed to take on multiple celestial enemies, including Lucifer himself.
10:WHEN I GROW UP
When Dean was younger he wanted no part in the family business. Since he was a kid he has wanted to be a fireman, a mechanic, and even a rock star. During his one year off he also spent time working in construction.
However, after being plunked into normal life and being exposed to a case even without his memories, it becomes clear that Dean is a natural strategist, leader, and warrior. “You’re a hunter. Not because your dad made you. Not because God called you back from hell. But because it is what you are. And you love it. You’ll find your way to it in the dark every single time and you’re miserable without it.”
In season one, Scarecrow, we get a glimpse of how Dean deals with witnesses on his own. After a very awkward attempt to try steer a couple away from danger, he mentions how his “brother, he’d give you this puppy dog look and you’d just buy right into it.” It becomes clearer over time that Dean struggles in social situations. He didn’t interact with other people in his youth very often, he generally spent his time looking after Sam or hunting with his dad. He did not have a real friend in all his young life. Although others were a part of life later on, like Ellen and Jo, his first real friend was Castiel, an angel. Cas is also incredibly awkward, a struggle Dean’s familiar with.
8: GREAT… BOOKS
Dean is very well read: he often mocks reading but has read most of the books in the bunker, Bobby’s house and reads in his spare time. He’s a big fan of Vonnegut and has read classics such as Aesop’s fables.
Dean is highly intelligent and well versed on lore. Back before the bunker, as far back as season one, he knew mythology from his father’s journal, such as the Wendigo, off by heart. In Phantom Traveller, he discusses the importance of biblical numerology in relation to a demonic plane crash. This isn’t a side of himself that he openly embraces, often leading Sam to be surprised when his brother knows something he assumes is more up his own ally.
Ironically, despite Dean being raised to hate the supernatural (a failing he begins to recognize in Bloodlust), his closest friend circle includes a fallen angel, a resurrected vampire, a werewolf, the King of Hades, and a centuries-old witch.
Whilst Cas is an angel, he’s made plenty mistakes, usually trying to do the right thing. Benny was a vampire Dean met in Purgatory; he willingly sacrificed himself to save Sam (who did not approve of him). Garth is a loveable hunter turned werewolf. Crowley and Dean been through a lot together and, despite his demonic ways, he will always come around to save Dean. And, of course, villain turned friend, the super witch, Rowena.
6:THE GOOD GUY ALWAYS WINS
Dean is huge movie buff, but he tends to hide his interests from people around him. He loves eighties horror movies: “I like to watch movies where I know the bad guy is gonna’ lose.” His favorite being “Hatchetman.” Dean also loves soap operas, particularly a parody of Grey’s Anatomy, set in “Seattle Mercy Hospital.” He is a secret fan of “chick flicks” and loves anime. He also deeply enjoys LARPING, after being introduced to “Moondoor” by Charlie. He’s also a fan of Scooby-Doo and even got zapped into an episode, becoming a cartoon.
Hunting doesn’t exactly pay… at all. The boys run credit card scams for most of their finances, but to keep police off their tail their spending is limited to essentials. They swindle pool frequently and Dean occasionally plays poker. This is something he frequently did in his youth to try keep money going when John wasn’t back in time. Losing his money to these games then being forced to get food using “sticky fingers” is what got Dean sent to a boys home. Card games are a skill he learned from Bobby.
4:CHILDREN ARE THE FUTURE
Dean spent a lovely night with a beautiful woman (Lydia) in season seven. It wasn’t until afterward that he realized she was an amazon, a ‘monster’/demi-god from Greek mythology. He also noticed the appearance of a surprisingly well-spoken baby who grew like Benjamin Button. “This morning, Emma was a baby. By sunset she’s Hannah Montana… early years.” Emma turned out to be Dean’s child, sent to dispatch of her father. Although her physical age was sixteen, she was only three days old. Whilst Dean was willing to help her and give her a chance, she ended up being put down by her uncle, Sam.
3:ONE IN THIRTEEN
In the first thirteen seasons, Sam has been possessed multiple times. However, with the exception of a parasitic monster, only one being has ever possessed Dean: the Archangel Michael.
“You’re my true vessel but not my only one… It’s a bloodline… Stretching back to Cain and Abel. It’s in your blood, you father’s blood, your family’s blood.”
In season five Dean was revealed to be the true vessel, every angel and demon assured he was “going to say yes.” It isn’t until the alternate Michael becomes the only option to stop a nephilium-charged Lucifer from destroying the universe, starting with Sam and Jack, that Dean fulfilled the prophecy.
2: I NEVER MISS A BEAT
It’s no secret Dean is a lover of music. He inherited his love of rock from his parents. When he’s stressed he hums Smoke On The Water to calm himself down. He also loves Led Zeppelin, an artist both his parents bonded over. Dean made a mix tape for Cas of his favourite Zeppelin hits when Cas lost his wings. He has been caught listening to music outside his typical ‘character’ rock multiple times. He often hides this, being a secret Taylor Swift fan, blasting Shake It Off in the impala.
The last thing Mary said to him before she perished was “Angels are watching over you.” Ever since, he has only ever believed that evil beings, like demons exist. He only believed in angels after he met Cas, ironically revealing that Dean was Heaven’s greatest weapon: The Holy Sword of Michael. She turned out to be right, although it ended up not being entirely positive. This is also something Kelly says to Jack (“You have angel watching over you.”) in her video to him.
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