Post 9x13 – Slightly Injured Sam/Big Brother Dean – Usually after a conversation like they had experienced the previous night, they would avoid each other, especially the next morning. But here Dean was. Because Sam needed painkillers and water and someone to call him on his BS...and all of that sounded like a job for Dean Winchester.
Pre-Series – Upset Sam/Big Brother Dean – While Dean couldn't bring their mom back, he could make sure his little brother felt safe and loved. He could make sure Sam's childhood included the things it should...like having cupcakes for the kid's kindergarten party.