Sam shooting Madison and even more, Dean crying when Sam had to shoot Madison. Winner in my book

All Hell Breaks Loose 2. When Dean is crying over Sam's body at Bobby's house. Cried... then my step dad laughed at me.

Madison, and the single tear from Dean.

Dean's speech to a dead Sam at the end of AHBL2. Sam having to kill Madison and Dean's one tear, jump reaction. Dean's speech at John's grave in WIAWSNB. Sam's heartbreak in Mystery Spot. The look in his eyes. Ellen and Jo's death.

Sam killing Madison & Dean's lone sexy tear; Ellen & Jo's Death for SURE; season 5 finale (had to watch twice cuz it was so shocking...one minute laughing then crying)

Dean's 'I'm tired' speech..."Fixing the Impala" scene...the scene when Dean winks at Sam before killing Zachariah...the fireworks scene Sam fighting against Lucifer, hitting Dean, stopping just as the sun glints off of the Impala and he sees the tiny green army man in the window... This part gets me everytime! And of course "Sammy, it's ok. It's ok, I'm here. I'm here. I'm not gonna leave you. I'm not gonna leave you.” This scene broke my heart!

Lucifer spotting the toy army guy in the car, and having flashbacks of Sam's life with Dean, followed by Lisa hugging a tearful Dean when he goes back to her after Sam is gone.

dean's response to sam killing madison, still not over dean telling sam, "i'm here, i'm here" when sam as lucifer, is beating him so badly, he doesn't fight back, just gonna be there for sam, no matter what. i'm kinda afraid that this emotion is going to be nothing compared to our 2 season finale eps! :(

when Ellen and Jo died. I loved Jo. When she was mauled by the hell hound and Ellen basically said there's no point in going out without my baby and stood there and died with Jo. definitely the moment that stood out the most to me. :)

Sam having to kill Madison, the camera zoom to Dean, his jump at the sound of the gun and his single tear. Dean holding his dying brother in his arms at Cold Oak and yelling, "SAMMMM!!!!" Dean going outside of Bobby's house to pray after Sam was put in the panic room to detox for the first time. Dean kissing Jo so reverently goodbye and Ellen facing the hellhound just before she hit the trigger to the bomb. The look of wonder and happiness on Dean's face during his memory in heaven as young Sam danced under the fireworks. Dean telling Sam he'd never leave him over and over as Lucifer made Sam's body beat the #@&* out of him.