Sam Winchester. His fate being predetermined for him despite him trying to distance himself from the hunting & supernatural life as a whole ... 💭💭 Also his relationship with religion......

Dean's a close contender (I have cried over him approximately 2 times now). She's so eldest daughter to me. I didn't like him at first (<- fell for the character façade award) but now that I look back at it, his life is genuinely so tragic. I can't imagine how he must've felt when Sam left for Stanford. Me when I'm at the dysfunctional family competition and the Winchesters show up: