I know my Dad better than anyone. And you ain’t him.
This scene kills me every time. I mean, how fucked up is it that Dean knew he was talking to a friggin’ demon because his actual dad would never say anything nice to him? How fucked up that Azazel gave himself away by acting like a more loving father than the man Dean actually knew?
And Dean’s face in that last gif? That’s the face of a man who’s trying as hard as he can not to cry, because this demon—the demon who ruined his family—doesn’t even know the full extent of how much he really fucked up the Winchesters, doesn’t realize that John never became the father he could have been. That look on Dean’s face is the face of a man who’s having the father he should have had, wished he had, parodied by the very monster who took that father away from Dean forever.
Let’s just take a moment to appreciate that this is the exact same way that Kevin knew that Crowley was using fake Winchesters in Season 8.