SPN Top 5 Heartbreakers

[amberdreams]

Posted this challenge at SSA but though you guys might like to play too.
I've done a wallpaper with my (current) top 5 heartbreaking moments from SPN, not really in any order but...:
1. Dean's speech over Sam's body in Season 2 AHBL (part 1)
2. Swan Song, Season 5 - that image of Dean slumped on the floor, maybe dying, Sam having sacrificed himself to cage Lucifer
3. The boys celebrating Christmas before Dean's deal comes due in A Very Supernatural Christmas, season 3
4. Season 5 again, Episode 2 when Sam leaves to go it alone... oh boys!
5. That moment Dean chooses to live (or risk dying) to get back to the real Sam in What is and Should Never Be (another Season 2)
Of course, there are many many more....So - what are the moments that have broken your hearts then?