“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 put 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.”

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.”

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.”

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.

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.

THE CHICAGO WAY

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.’

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.

DO YOU BELIEVE IN FAIRIES?

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.

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.

HE WAS BORN FOR THIS

Dean, whilst being “raised in the life,” still had moments of doubt. Particularly evident in Bad Boys when we see his younger self it 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.”

HE'S QUITE THE TECCHY

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.