Tracy’s never ending list of favorite scenes → Rock and a Hard Place
Reason: In the past, Dean has always been very careful with his money, and he has almost never given any away without Sam telling him to, and when he did, it came with a huff or sigh or some kind of retort to Sam afterwards. But here, Sam isn’t telling Dean to give Slim some money, Dean simply digs into his pocket and pulls out a few bills for the homeless man. Dean didn’t look over the dirty, probably smelly man and grimace, he instead smiled at him and was compassionate and appreciative. And Slim seems shocked by his act of generosity. You want to talk about character development? Let’s start with this scene.