The first and probably most obvious award goes to:
Jensen Ackles for Best Actor, for "What Is And What Should Never Be" s2 e20
I think this was the one that made me fall in love upon first watching it months ago. And upon a couple of rewatches, it's still abundantly clear that this episode, which Jensen told an interviewer was the most difficult he'd filmed yet (said interview taking place during the filming of season 3) due to the extreme emotion it required from him as an actor. He definitely doesn't disappoint. Dean's longing, his yearning to be loved in a tangible way by the mother he thought he'd lost forever is so very real, you can feel it jump out of the screen and into your own heart. It doesn't hurt that we, the audience, haven't really experienced this side of the character until this episode---sure, we know he cried at his father's cremation, we know he loves his brother, we know he has a savior complex and feels all the guilt of the world...but we never knew how much he simply misses his mother. Until now. Jensen is a revelation in this one. As we process the fact that his ultimate heart's desire is to have never lost his mommy---well, how can we not empathize? And he plays it so perfectly---caught between the desire to stay in that emotionally satisfying place, despite its artificiality, and the competing urge to get back to the brother he knows...and who knows him, and who needs him, back in their shattered life in the real world. A beautiful performance.
NEXT:
Jared and Jensen for Best Brotherly Beat-Downs in:
"When The Levee Breaks", s4 e21: Jared whumps Jensen pretty hard because Dean called Sam a "monster." Dude, that's no way to talk to your brother! Sorry, pretty boy, but Sam hasn't even started drinking demon blood yet but locking bb bro in Bobby's panic room is just so jaw-droppingly wrong, I don't care what he'd done "wrong" according to you. You totally had that coming. Plus, it's nice to see Sam get some for a change...
"Metamorphosis", s4 e4: Jensen bitchslaps Jared hard, twice, after uttering the immortal line, "If I didn't know you, I would wanna hunt you." Yeah, it's all about the lying, hiding and drinking demon blood.
And my favorite,
"You Can't Handle The Truth", s6 e6: Jensen totally beats Jared into unconsciousness after Sam reveals that yeah, okay, he's known that something's been wrong with him for over a year, because he just doesn't care much about anything and doesn't really feel any feelings...and okay, he actually did let Dean get turned by that vampire, but hey, he knew it would all end up just fine cuz, you know, Dean's so strong, and he knew they had a cure...then KA-POW! Dean loses his mind and delivers a frenzy of hard punches to Sam's (beautiful) face, and Sam's down for the count. But it's Soulless!Sam, so I was OK with it (well, more OK with it than I would've been otherwise), and it effectively set up the long process of getting Sam's soul back, so...no pain, no gain.
Thank you to: the stunt coordinators, the stunt doubles, and the writers for setting up these Boys Hitting moments, without which the Boys Loving moments wouldn't be as cathartic...big round of applause for all!