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5. Sam and Lucifer reunited - "O Brother Where Art Thou?"
I think this moment could have been executed better, but there is no doubt that it has major significance in the “Supernatural” landscape. Sam spent several episodes conquering fears, including taking on a homicidal clown (yes, it’s every bit as golden as it sounds) to get to this moment, confronting the worst terror he ever experienced. The idea of him going back to the cage brought him to tears a few times, but he did it anyway, convinced that God was the one sending him those messages. It was a big character growth moment for Sam, and all it did was leave us gut-wrenched going into winter Hellatus as Sam's worst fears about the outcome came true. He's stuck in the cage with Lucifer and getting plenty of mind games about who actually sent the visions. The poor guy can't catch a break.