Sam and Dean have come a long way. In Supernatural‘s pilot, Sam was the college student preparing for law school and a life with Jess, picket fence and all. Dean and his leather jacket were on the road, where the good soldier was obeying dad’s orders at every turn. But when dad went missing — “Dad’s on a hunting trip and he hasn’t been home in a few days” — everything changed. What started as a weekend commitment (Sam has to be back first thing Monday for his law school interview!) turned into a 13-season adventure … and it’s still going.
Supernatural fans have watched the brothers hit the road time and time again to hunt everything you could imagine and more. (Bet you didn’t see that talking teddy bear coming, did you?) With each trip, the brothers learn something — about their job, about the world at large, about themselves. And along the way, the actors learn more about the characters they first met all those years ago. “Dean was written pretty well. [I had a] very good understanding of the character from the get-go,” Jensen Ackles says. “The way that he came in and recruited his brother and the way that he reacted to his brother saying, ‘Anything you have to say to me, you can say in front of my girlfriend.’ It was like, ‘Alright, well, here we go.’ That gave me the ‘devil may care’ side of him.”
Three episodes later, Ackles would realize another layer to this Dean Winchester guy. (And no, it wasn’t his love of pie.) “A big [episode] was ‘Phantom Traveler,'” Ackles says. “It was the first time we saw Dean be scared and so scared that it was comical. That comedy element revealed itself.”
And while it’s not pie, Dean’s love of food would eventually make itself known, giving Ackles another element of character development. Specifically, Ackles remembers a moment from “Nightmare,” the 14th episode of season 1. “The eating of the cocktail sausages at the person’s house in the first season then peeled back the layer of Dean’s affinity towards food,” Ackles says.
It would be a few years before Dean’s next turning point, which Ackles identifies as “The End,” the fourth episode of season 5. “The glimpse into the future where we saw five years ahead and saw how dark Dean could go — even though it was a very difficult episode and one of my favorite episodes—it gave me an insight of: That exists in him,” Ackles says. “It was a glimpse of what not only the world could be like but what he would be like if certain events were to occur.” Just like that, Dean had become a lot more than the protective older brother who wanted to please his father.
Then there’s Sam, who took an entire season to warm up to the idea of hunting. Specifically, Jared Padalecki says the first episode of season 2 marked a turning point for the youngest Winchester. “Episode 1 of season 2 is when Sam started to accept that he had a different calling than maybe he would’ve thought prior,” Padalecki says. “I feel like that was the first real major one where it’s like, ‘Okay, Sam’s in it now.’ [In season] 1, Dean pushed the storyline like, ‘Hey, we got to find dad.’ And then Sam in season 2 was like, ‘Okay, I can do this.'”
Jump ahead a few years and the smiley college kid who’d put hunting in his past would be nothing but a memory. Not only had Sam embraced the hunting life, but in season 4, he toed the line of becoming the very thing he and his brother spent their days (and nights) hunting. “In season 4, he kind of went off the deep end,” Padalecki says. “Sam has very much embodied ‘the road to hell is paved with good intentions.’ He’s tried to go out on a lot of different limbs. We saw that with season 4 with Ruby and the demon blood and Sam trying to almost get rid of himself, if necessary, to stop the apocalypse and kill Lilith.”
Eventually, Sam would find his way back to the good side, so much so that in season 8 he was willing to risk his life for the good of the world. “In season 8 where Sam has to do the trials, we see that he’s gone from, ‘Let me go to school, I want kids and a wife’ to now he’s full steam ahead,” Padalecki says.
Season 9 would then test Sam when, as Padalecki puts it, “Sam was losing Dean.” With the Mark of Cain threatening his brother’s life, it was Sam who learned the most about what mattered to him.
Altogether, Padalecki says those major moments have gotten Sam to where he is now. As for where “now” is, it involves the son of Lucifer, alternate universes, and even more layers being pulled back on our favorite apocalypse-stopping brothers. After all, it takes a while to really get to know someone. Because you can’t judge a person by his flannel.