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"Come on. Really? Man." Dean, "Phantom Traveler"
Oh, he's so scaredy! Poor scaredy Dean. He sounds so exasperated at this point. And it was pretty funny to learn that Dean could hunt all manners of creatures with no problems but flying turned him into jello.
"Oh, that's right. I did. Still, two wrongs don't make a right." YED!John, "Devil's Trap"
This is my favorite Jeffrey Dean Morgan line reading ever. Wow, was it mean and nasty and fantastic. I mean, he really twists the knife here. The "two wrongs" part is amazing.