Sam and Dean are the best because despite all the doom and gloom they go through they can still find ways to enjoy themselves. They'll never give up on each other and they will continue hunting monsters until the world is ready to say goodbye to Sam and Dean Winchester. Let's hope it's not too soon!
Dean first love is baby but he still took time to show Sam how to take care of her. Of course he was showing him how to fix her because he was going to be dying but you still have to appreciate Dean letting Sam have some control.
A lot of people would cal Dean refusing to close the door to hell as selfish but Dean has never minced words when it comes to his brother. It's always just been Sam and Dean against the monsters of the world.
Remember when Sam was excited for Christmas but was quickly disappointed when he found out their dad wasn't going to be there? Dean took it upon himself to get Sam a gift -- though he stole it but it's still the thought that counts.
Pretty sure that this is everyone's favorite iteration of Dean Winchester. Demon Dean only lasted about two episodes but even in that amount of time there was a change in his style of dress that lasted throughout his darker Season 9 arc. Like Will Graham, Dean Winchester is mostly seen in jeans, flannel and hiking boots, reflecting his Midwestern roots. During the darker season however, his shirks all of the above for slimmer, black jeans, leather and darker toned t-shirts. Since he is very firmly not a demon for most of Season 9, this change in costume style seems more so to reflect his darker mood as he deal with the curse on the Mark of Cain. We have to say though, leather jackets definitely look good on this character.