I gave this a few weeks to settle after finishing my rewatch and this is what's risen to the top. I'll do it again in another year or so!
1.
3x08 A Very Supernatural Christmas
The Christmas scene in the motel at the end is hands-down my favourite scene in the show. It's just brimming with love. The initial camera shot of Dean's amulet as he comes through the door, following the flashback that explained where he got it, is perfect. Dean looks so happy and Sam looks amazing in his white patterned shirt, the same one he wore in the beautiful scene at the end of What Is and What Should Never Be. When I first saw this, I sent
sarren an email saying my heart was in little pieces all over the floor, and I still feel that way every time I watch it.
I also like the bright colours of this episode: the Christmas decorations and lights, the greens in the motel room, the red walls of the Carrigans' house.
2.
5x16 Dark Side of the Moon
I know a lot of people of taste don't like this one, but in my opinion they're not giving enough weight to canonical soulmates in Heaven. Plus, there's the beautiful fireworks scene, Dean's "If I'm in Heaven, where's Sam?" and the "But I'm your family / It's supposed to be you and me against the world" conflict:
Sam: Man, I never got the crusts cut off my PB&J. I just don’t look at family the way you do.
Dean: Yeah, but I’m your family.
Sam: I know…
Dean: I mean, we’re supposed to be a team. It’s supposed to be you and me against the world, right?
Sam: Dean, it is!
Dean: Is it?
Dean's "Is it?" is one of the more heartwrenching moments in the series.
I don't mind that the memories that we see of Sam's are of times he was on his own, and I don't think they're meant to be entirely representative of his most cherished moments. Are we supposed to think that listening to his parents fight is one of Dean's most cherished memories? Presumably not.
It's an interesting episode too, in that it goes out on a limb and presents a vision of Heaven. I love that it's not really that great, and Dean recognises that right away. To Pamela: "Spending eternity trapped in your own little universe while the angels run the show, that’s lonely. You know. That’s not Nirvana. That’s the Matrix." But Dean's heaven won't be so lonely, it will have Sam in it!
At the end, unlike Dean and Cas, Sam still believes they can win and tries to share his conviction with Dean: "We’ll find another way. ... You and me, we'll find it." Sam reminds me of that "Never, ever give up" cartoon.
Yes, this episode has the throwing away of the amulet, and it's hard to believe that Sam never thought about how his two weeks in Flagstaff affected Dean, but those things don't even come close to outweighing canonical soulmates in Heaven. I'll say it one more time: canonical soulmates in Heaven!
3.
2x21 All Hell Breaks Loose Part 1
This one makes my No. 3 spot by virtue of the first two and a half minutes and the last two. I love the smile Dean gives Sam when he sends him into the cafe for burgers. The great emotion of the end is everything I could ever want. The opening and closing segments both end with Dean shouting Sam's name, which never gets old. I also like Dean being driven to his knees by the vision Andy sent him!
4.
2x22 All Hell Breaks Loose Part 2
Contains my favourite hug in the series to date and Dean saying "You almost died there. I mean, what would I have-." I also adore the moment when he swings the Impala onto the road as he heads for the crossroads and drives with both hands fixed grimly on the wheel, and his meeting with the crossroads demon, who is a very nice example of her kind ("It's a fire sale and everything must go."). I fast-forward through most of the Yellow-Eyed Demon stuff, just like in Part 1 I skip most of the middle of the episode, but the great stuff in these two episodes is so incredibly good that they're Top 5 even so.
5.
5x22 Swan Song: for the stargazing scene and the narrated history in which we learned that they sometimes went to concerts in their downtime, "I'm not gonna leave you," the Sam/Lucifer flashbacks, and the state of Dean when he goes to Lisa's. I'm still not entirely convinced that Dean would let Sam condemn himself to Lucifer's cage, but if I don't dwell on that, this is a tremendous episode.
Rounding out my Top 20, in rough order:
4x17 It's a Terrible Life. I'm not normally one for AUs, but I find this episode very rewatchable! Partly I like the corporate setting, since that's my own background. It's mind-bending to watch Dean as a marketing executive, and his car is particular is so, so wrong! I find Sam and Dean's interaction in it quite moving, especially on Sam's side:
Sam: Remember those dreams I told you about with the ghosts?
Dean: Yeah?
Sam: I was fighting them.
Dean: Okay.
Sam: With you. We were these, like, hunters, and we were friends. More like brothers, really.
I want to believe that Zachariah is right, and that Dean really would choose hunting over any other life.
This is another colourful episode, thanks to the brighter-than-usual lighting and Sam's yellow shirt.
2x20 What Is and What Should Never Be for the pain of AU!Sam and Dean's interactions, and the final scene between real Sam and Dean in the motel. Dean’s still shaken and sad and Sam looks wonderful in his white patterned shirt.
Dean: Should have seen it, Sam. Our lives. You were such a wussy.
Sam [with a particularly beautiful smile]: So we didn't get along then, huh?
Dean: No.
Sam: Yeah. I thought it was supposed to be this perfect fantasy.
Dean: It wasn't. It was just a wish. I wished for Mom to live. Mom never died, we never went hunting and you and me just never... you know.
Sam: Yeah. Well, I'm glad we do.
Sam's "Well, I'm glad we do" (get along) is about as close to an "I love you" as I think we're going to get.
3x16 No Rest for the Wicked for the goodbyes.
5x10 Abandon All Hope.... I love the bravery with which Jo and Ellen died, and I really like the Sam and Dean scene at Bobby's, when the others are in the kitchen and they're sitting on opposite sides of Bobby's desk talking:
Sam: It's gotta be a trap, right?
Dean [smiling]: Sam Winchester, having trust issues with a demon. Well, better late than never.
Sam [also smiling]: Thank you again for your continued support.
Dean: You're welcome.
[They clink beer bottles and drink.]
7x07 The Mentalists. Reconciliation! I also love Dean joining Sam at the new-agey cafe and talking non-stop because he was afraid to give Sam the chance to tell him to go away.
Another colourful episode, due mostly to the yellow walls in Melanie's house!
7x02 Hello, Cruel World for breakfast in bed and Dean using his Hell experience to reach out to Sam.
5x21 Two Minutes to Midnight. Contains my favourite non-Sam and Dean scenes: Death's arrival in Chicago and his meeting in the pizza parlour with Dean.
6x15 The French Mistake. Again with the AUs. If you described this episode to me, I'd tell you I'd probably hate it, and yet it makes me laugh every time and warms my heart with "We're not even brothers here, man."
2x10 Hunted for the reveal at the beginning that John told Dean he might have to kill Sam, Dean's pleading to Sam to lay low for a while, the neck-holding after Gordon fails to kill Sam, and Dean's "I can try" (to protect Sam).
6x01 Exile on Main St. for the look on Dean's face when he wakes in Lisa's bed after dreaming of Sam, and the incredibly painful montage contrasting Dean's old and new lives.
7x10 Death's Door for the movie night. I'm a complete sucker for that sort of scene.
2x08 Crossroad Blues. My appreciaton for this episode is kind of retrospective in the light of what Dean does later, but I also just like everything to do with crossroads demons. What a concept.
1x20 Dean Man's Blood for Sam and John's argument, and Dean breaking it up.
4x01 Lazarus Rising for the reunion hug and the introduction of Castiel.
1x11 Scarecrow for Dean telling Sam that he admires the way he stands up to John.