Created by Eric Kripke and produced by Robert “Bobby” Singer, Supernatural is one of the longest-running shows on CW (previously the WB). The series follows Sam (Jared Padalecki) and Dean Winchester (Jensen Ackles) as they fight and/or team-up with an assortment of monsters, angels, demons, demigods, and other entities. Having premiered in 2005, the show has a dedicated fanbase and is now it its 14th season, with (hopefully) no signs of ending any time soon. The show has its own convention, and several charitable events/organizations including Stands and Misha Collins' GISHWHES.
The original concept for the show was more of a weekly monster hunt, and while a part of that idea survived, it also evolved into something more. They hunt monsters, but there are also season arcs and in-depth storylines that drive the show forward.
While the show premiered in 2005 and introduced audiences to Sam and Dean as adults, their backstories were often revealed in flashbacks. These flashbacks showed what their life was like before season one – including mistakes they made, adventures they had, and monsters they faced. There are a few instances of time travel as well, when the boys have to go back to witness certain events or acquire objects (maybe even putting certain things into motion). These events, so far, typically take place before they were born. Naturally, Sam and Dean aren't the only Winchesters whose backstories are revealed throughout the series.
With that said, let's take a look at the 20 Crazy Things The Winchesters Did Before Season 1 Of Supernatural.
DEAN KEPT SECRETS DURING HIS RELATIONSHIPS
It's debatable as to whether or not Dean should have told any of his love interests about monsters, aside from when they were in danger. With Cassie, his first real love, he told her after they dated for a while. However, it backfired. With no proof to back up his claims, she didn't believe him and broke up with him. It was later revealed in season one that she had done this because she believed he was trying to break up with her.
However, in his relationship with Jo, this wasn't an issue because even though she wasn't allowed to be a hunter initially, it was already a life she was familiar with through her mother. However, with Lisa, he ended up having to erase her memory of him. Whatever his reasons, his romantic relationships were just as shaped and hindered as Sam's when it came to the family business.
JOHN AND MARY FELL IN LOVE BECAUSE OF CUPID
Season 5's episode 14 features Cupid and Famine, one of the Horseman of the Apocalypse. While it initially appears that a Cupid has gone rogue and is claiming the lives of his targets, it turns out that the real culprit is Famine. However, when Sam, Dean, and Castiel questioned the Cupid, they learn that Mary and John Winchester actually disliked each other when they first met.
Even though there was an initial connection, it was Cupid's intervention that finalized their relationship. Cupid explained that Mary and John's relationship was a big deal in heaven because of destiny. The fact that they got together in part because of Cupid is surprising. It certainly was to Dean, since he ended up socking Cupid.
DEAN STOLE PRESENTS FOR SAM WHEN THEY WERE KIDS
In season 3 episode 8 “A Very Supernatural Christmas”, flashbacks reveal the day young Sam Winchester learned about “hunting” and what his father and brother already knew about monsters. He confronts Dean about this, and at first Dean tries to deny it. However, he finally admits to him that monsters are real. This is upsetting for Sam.
Later in the episode, Dean comes back with some presents for Sam to cheer him up. When Sam opens the presents, they turn out to be a special-edition Barbie and a baton. At that point, Sam knows what happened, and Dean admits that he stole them from a house up the street. Since they were by themselves, that action could have gone horribly wrong. If Dean had been caught, who would be there to look after Sam until their father returned?
SAM BECAME FRIENDS WITH A MONSTER... BEFORE DEAN TOOK ITS LIFE
When he was younger, Sam unknowingly befriended a Kitsune, named Amy, while hunting. The primary food of the Kitsune is human pituitary glands, and it turned out that her mother was the one taking people's lives in order to feed them. Her mother was ruthless and wanted to take Sam's life. However, Amy saved him, and he let her go when she promised that she wouldn't live like that.
Unfortunately, she wasn't able to keep her promise because she had a sick child who needed fresh food. However, Sam let her live a second time. Despite the fact that it was only bad guys she went after, Dean ended her life in one of the most hypocritical moves he has ever made. It became a point of contention in later episodes.
SAM WENT TO COLLEGE INSTEAD OF BECOMING A HUNTER
In season 5 episode 16 “Dark Side of the Moon”, the brothers discuss how Sam ditched Dean and their father in order to go to Stanford to practice law. This is something talked about throughout the series, and it is how we're introduced to Sam in the first season. Dean has to go get him at college because their father is "on a hunting trip and he hasn't been home in a few days.”
In this episode, it is obvious to Dean that Sam never really cared about family as much as he did. For Sam, it was a matter of choice, but he was also selfish. Because of how he was introduced to the “family business,” he didn't quite understand the importance of what they were doing.
DEAN FOUGHT COLE TRENTON'S DAD
In season 10's episode 2, we learn that Dean had a confrontation with Cole Trenton's father in 2003 . He was possessed by a demon, and Dean did what hunters normally do in that situation. From that point forward, Cole vowed to get revenge against the man who took his father away from him. However, even though he was militarily trained, he was not ready to face off against the new Demon Dean.
Crowley then had given up the “uncontrollable” Demon Dean to Sam, who captured him after the fight. Before that, though, not only did Dean beat Trenton easily, but he also let him know about demons. Dean didn't think of the potential consequences at that time, but Cole (with newly acquired knowledge on how to destroy demons) would later come back to try to finish Dean.
SAM AND DEAN SET FIRE TO A FIELD WITH FIREWORKS
In season 5's episode 16, Dean and Sam end up in heaven after two hunters decide they have to go. No matter how many times they've been caught off guard, it's still surprising. Once we get past what seems like an impossibility – two other hunters not only getting the drop on them, but they also steal Dean's weapon from under his pillow while he sleeps – the episode goes on an interesting romp through some of the boys cherished memories.
Most of these take place when the brothers were children. Dean remembers when he and Sam were playing with fireworks and ended up burning up a field, though this scene is never shown. They could have done worse damage than they did, but fortunately luck was on their side.
SAM AND DEAN SAVED THEIR PARENTS
In season 5's episode 13, Sam, Dean, and Castiel go back in time to save young John and Mary Winchester. This time, angels are after them. Anna is sent to take down Sam Winchester, in hopes of stopping the apocalypse by preventing Lucifer from having a viable vessel. This is risky, of course, because Sam and Dean will never be born if they screw up. However, it turns out that that's exactly what they want.
While they're thinking that they'll stop the apocalypse, they fail to consider all of the lives that they would save up until that point. They even try to convince Mary to leave John, but she refuses. In the end, they manage to save their parents with the help of Michael, who erases John and Mary's memories of the event so things could proceed as intended. It's too bad that it wasn't Gabriel that he was dealing with, though, since at least he can be reasoned with.
JOHN BOUGHT THE IMPALA BECAUSE A STRANGER SUGGESTED IT
The first time that Castiel sent Dean back in time to his parents, Dean was able to convince his father to buy the '67 Impala. While in the comics the origin story of the Impala is changed – it was purchased after Mary passed away – in the show it was an important part of the boys' childhood. The car is an essential character as far as the show is concerned.
Baby has gotten the boys through many tough situations, and the car itself has gone through numerous changes, especially when it was rebuilt after it was totaled. That moment between John and Dean is an important one. It's possible that, with the way the timelines work, John never would've bought the Impala if Dean had not gone back in time.
DEAN HELPED ELIOT NESS
In season 7's episode 12, Chronos sends Dean back in time. There, he meets Eliot Ness in 1944 and learns that he is also a hunter. Together, they have to stop Chronos from aging people before their time, and find a way to get Dean back to his own time.
Dean is a big fan of Ness', so he's pretty excited about the whole thing, except for the fact that he might not be able to get back. However, with Sam's help in the future, Ness and Dean are able to defeat the God of Time by bringing him back to their present timeline and using a special stake against him. There were a number of things that could have gone wrong (or right) with Dean being in 1944. Unfortunately, he wasn't able to end the lives of any dictators, since he didn't meet a resurrected version of Hitler until much later.
DEAN LEFT SAM BY HIMSELF AND A SHTRIGA ALMOST GOT HIM
There were many times when Dean and Sam were left on their own when they were kids. On one occasion, young Dean became restless and decided to play video games. When he got back, though, the monster that John was hunting was trying to steal Sam's life essence. Because of this, Dean felt guilty about leaving his brother alone. However, John probably should have had another hunter watching them while he was away, especially since he knew that the monster was in the area and he had two young children – the Shtriga's particular choice of victim.
Many fans didn't notice that the woman in the park is angel Hannah in seasons nine and 10. In later seasons, it's revealed that specific playgrounds are guarded by angels and used as entry points to Heaven.
JOHN NEVER TOLD SAM AND DEAN THAT THEY HAD ANOTHER BROTHER
Dean and Sam quickly learned that John had a lot of secrets. One of them turned out to be that he had another son. After being injured on a hunt, he met Adam's mother Kate in a hospital where she was taking care of him. Meeting their brother Adam was a complete surprise to Sam and Dean, and they both dealt with it in different ways.
According to Dean, John might have kept Adam a secret from Dean and Sam because he wanted to protect Adam from the life that was forced upon him and his other sons. Nevertheless, it turns out that the Adam who they meet is not really their brother, but a ghoul who takes on his form in order to exact revenge on John. They later meet the real Adam after he is brought back to life in order to become Michael's vessel.
HENRY WINCHESTER HID HIS IDENTITY FROM HIS FAMILY
In another twist of fate, Henry Winchester, who was a Man of Letters, never told John about monsters and what he did. It turns out that being in the Men of Letters is passed down from generation to generation. Instead of becoming hunters, John and his sons were supposed to become Men of Letters.
However, Henry never had a chance to tell his son about the group because he disappeared one night and never came back. It turned out that he had accidentally traveled to the future to escape from Abaddon. If he had told John about his secret identity, then maybe things would have been different for John and Mary. Perhaps they would've been able to defeat Azazel before he caused the damage that he did to their family.
SAM AND DEAN OBTAINED PHOENIX ASHES
After they learn that the Mother of All/Eve can only be destroyed by the ashes of the Phoenix, Dean comes up with a plan that involves him and his brother going back in time to the 1800s to meet Samuel Colt, the maker of the gun that can destroy many different types of monsters. They believe that if they can be there when he faces off against the Phoenix, they can gather the ashes and use it against the Mother of All.
This is a huge gamble on their part since Castiel is in the middle of a war, and the amount of time they have to go back and retrieve the ashes is limited. Despite their efforts, though, they're not able to get the colt. However, it is delivered to them after they return.
JOHN BECAME A VESSEL FOR MICHAEL
When Sam, Dean, and Castiel traveled through time to save John and Mary, John ended up letting Michael use him as a vessel in order to save Mary from Anna, the angel sent to take their lives. Since he didn't know much about angels, it seemed reasonable why he would be okay with this. However, it is pretty surprising to fans, who know how Michael treats the Winchesters on the show.
Dean was also surprised to see Michael use his father as a vessel. However, it turned out that Michael could use specific Winchesters as vessels because of their particular bloodline, which meant that this wasn't just specific to Sam and Dean. After learning this, Dean was somewhat despondent, as he believed for a time that there was no way to change fate.
MARY NEVER TOLD JOHN SHE WAS A HUNTER
When Dean is sent back through time to meet his mother, he learns that she and her parents are also hunters. It turns out that Mary knew about monsters and demons before even John did. She never told John that she made a deal in order to bring him back to life after the same demon took his life.
Dean tried to intervene with their fatel, but when he was brought back to the present, Castiel let him know that he was only meant to see what happened, and thus he wasn't able to stop it. By keeping the fact that she was a hunter a secret from John, Mary left her family vulnerable. However, much like Sam, she wanted a normal life more than anything else.
SAM RAN AWAY AS A TEEN
In season 5's episode 16, Dean and Sam see a memory that Sam has, one that turned out to be a favorite of his. He stayed in a rundown place by himself, except for a dog he took in at the time. He mostly ate pizza and did whatever he wanted. We learn from Sam's perspective that this is one of the happiest times of his life.
For Dean it was one of the worst times of his life, because it was when Sam had run away as a teenager. Their father blamed Dean for Sam leaving and gave him a hell of a time about that. Sam never thought of the consequences and how Dean would feel, believing he might never see his brother again.
JOHN TAUGHT SAM AND DEAN TO BE HUNTERS
The entire show revolves around the fact that the boys were introduced to hunting at a young age, after their mother, Mary, was ended by the yellow-eyed demon. Without this, it seemed possible that they could lead a normal life. While the show goes back and forth as to whether or not John should have done this, it's certain that Sam and Dean save lives.
They're the best hunters around, and might not have been if it wasn't for the training their father gave them, and through that the extended family and friends they had – people like Bobby (Jim Beaver), Ellen (Samantha Ferris), Rufus (Steven Williams), Charlie (Felicia Day), Kevin Tran (Osric Chau) and Missouri (Loretta Devine), among others. It's possible that they would have been inducted into that life another way, especially since Sam already had demon blood in him and they were both destined to be the vessels of the archangels Lucifer and Michael. Chuck (Rob Benedict) probably wouldn't have written it any other way.
MARY MADE THE DEAL WITH AZAZEL
One of the biggest defining moments of Sam and Dean's lives happened before they were even born. Had their mother not made the deal with Azazel, the two of them would never have been born, though not making the deal would have saved Mary's life.
However, in the apocalypse world in season 13, Mary never had any children. Sam and Dean were not born in the apocalypse world, therefore they weren't there to stop Michael and Lucifer from taking other vessels and creating Armageddon. Because Mary tried to protect Sam and Dean by hiding that frightening truth from them, they weren't prepared. Because of this, John and the boys spent a large chunk of their lives trying to unravel the mystery of what happened to her.
SAM THREW UP AT A HALLOWEEN PARTY
Jared Padalecki was in a Friday the 13th reboot, and an episode of Supernatural slyly referenced that by having Sam dislike Halloween. At the end of the episode, Sam explains why he doesn't like Halloween. The reason he gives is that he had a crush on this girl as a teenager and, since he was nervous, he threw up all over her at a party. This cleared out the entire event. Though it's a surprising revelation, it's not exactly a fond memory.
Aside from that, the episode was full of other goodies for fans of Supernatural and horror/sci-fi. Jensen Ackles and Stephen Amell (Arrow's Oliver Queen) have been trolling/teasing fans of Arrow and Supernatural with the ideas of a crossover of some sort. Some fans even believed Jensen might be playing Batman on Arrow. This was referenced in the episode with a Red Hood costume as well, since Ackles voiced an animated version of the DC character.