These all apply to him so much.

One of my favorite things about supernatural is how S01 established Dean as this stereotypical masculine guy then went on to absolutely destroy everything stereotypical about his character in later seasons while still keeping his characterization pretty consistent

I would argue that he was never actually a “stereotypical masculine guy” - if he had been, there would be nothing important and valuable to have built on from the beginning, and yet from the start so much depth and such a study of contrasts existed there, the tenderness always co-existed with the ferocity, not separate fragments of his self or his heroism, but balanced elements. he’s multi-faceted, both aspects are true. he was allowed to grow and to break those tropes down and to allow further truths and capacities to manifest as he shed and questioned the facade he’d been trained to carefully construct, but that persona was never a whole being, it was never the picture of who he is. he is still challenging expectations, walking the lines between definition, and there’s a fascination in that, it adds power to his existence.