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8. Cass expresses his doubts in "It's the Great Pumpkin, Sam Winchester"
This was only the fourth episode Castiel was in, and the first three painted him as an angel who was sympathetic to the Winchesters' cause but was still heaven's soldier and would do what was necessary to stop the apocalypse. So for him to come to Dean at the end of the episode and express that he was having doubts about heaven's plan, that he was rooting for Dean and wanted him to succeed, well, that was pretty huge. That moved him from rogue angel to probable ally, and it was the start of the deepening friendship between Dean and Cass.
7. Three demons bite the dust in "The Man Who Would Be King"
This was so super badass. It's awesome when Cass gets to go all BAMF, and this was one of his finest kickass moments. Two demons in your way? Smite them both! And how do you follow an excellent smiting? With an even more excellent smiting! Who cares if that demon is trying to smoke out of its vessel? Smite it anyway! Vengeful wrath at its finest.
6. "We had an appointment" in "The End"
Talk about best timing ever! Stubborn old Dean hadn't learned the lesson Zachariah wanted him to during his trip to the future, so what's left to do but send Dean back again and again until he does? It's a frightening prospect. How many times can Dean watch his brother be Lucifer, watch his brother kill him before he snaps? Blessedly, before Zachariah is able enact his nefarious plan, Cass shows up and brings Dean back to the past. He told Dean he'd wait for him, and he did. It was just such a wonderfully Cass thing to do.
5. Cass blasts four angels, including himself, into oblivion in "Point of No Return"
This moment was pretty amazing, but it was pretty heartbreaking, too. I mean, before he went into the warehouse to fight off those angels, he basically tells Dean he'd rather die than watch him fail. Ouch. Because, really, Cass has no idea what's going to happen to him when he blasts himself away with that sigil. But he knows Sam and Dean have to get into that green room to rescue Adam and thwart Zachariah, so he takes the box cutter and goes to work. Of all the lessons he's learned from the Winchesters, he's taken self-sacrifice to heart most.