For all that their traumas have only accrued and all the allies they’ve lost, in the last 8 years Sam and Dean have actually managed to make hugely important gains. They have a library of new and powerful allies like Rowena. They have a literal library that for all its poor organization has really given them a lot. At the end of S13, however deeply unmatched they still were, the playing field’s been leveled a lot. Heaven has come down a lot, for sure—the chaos that was brewing in S4 and warring in S5 has been bombed and emptied now for years. If the world had hierarchies—Heaven, earth, Hell—these are flattening. S8/9 may have been about the chance to seal and separate them, but really they’ve just been headed for collision. Mundiphagy. (That’s not word but it might need to be one headed toward S14. World-eating.)
On a personal level Sam and Dean have definitely found ways of dealing with their lives that work a lot better than what they were doing in S5, as well. Because if things were messy in S13 (like, “throat ripped open dead in a mineshaft” messy, or "we have 36 hours to find two people in an entire world full of danger and not much transportation to speak of so let's get to it??" messy) both Sam and Dean were a true mess by the end of S5, in ways that are actually stunning by comparison. Poor babies, they were so sleep-deprived and so mentally all over the place. <333 Which isn’t to say that isn’t still the case now but Sam and Dean both had scenes in 5x20 where they didn’t know what to do in the face of impending Apocalypse and they just sat down in an ugly chair like “Well. Fuck, I guess.” D; </3
Also Sam was drinking excess amounts of hard liquor straight from the bottle and drunk-dialing Bobby and Dean was following Crowley with little resistance, to the point where it seemed more like he was doing it because it had plopped in front of him and was the path of least resistance (even if "least" here means "get the shit beat out of you") and less because he really thought it was the best--or even only--plan. It's not that he was enthusiastic about working with Crowley, per se, but we've definitely seen him broker similar partnerships (including with Crowley) with a little more caution, and a sharper idea of what it is. They are just totally stripped and exhausted by the end here, and it's so sad.
Some of my favorite scenes/characters in 5x20:
THIS GROTESQUE SINK
THE DRAMATIC ZOOM SALT
And because I’m me, here’s your 5x20 Dean H/C overlay: Dean gets his ass handed to him by Brady, which begins with multiple, forceful kicks to Dean’s trunk, from which Dean is powerless to recover in a timely manner. When he finally makes his way to the elevator, he’s using the corner and the handrail to keep himself standing. He probably broke a few ribs.
Then he’s sitting in this beautiful ugly chair kinda peaced out, which is one of the “well, fuck I guess” scenes aforementioned.
There’s nothing for him to do in this moment and he’s not up to trying to force himself into having anything. He’s just sitting in this chair in an awkward position that I like to attribute to his ribs, making this face:
Then Sam locks him in the bathroom with the grotesque sink by just placing a rickety chair under the doorknob. And it’s such a jank door on a warped frame, I’m pretty sure Dean would’ve had the capacity to destroy it—that is, if he hadn’t broken a bunch of ribs. Mmmmm.
I also love the ending scene in 5x20, because it’s like… This guy’s supposed to save the world in two episodes and he just shanked someone in a dark alleyway while his brother watched. Then he stalked away without saying a word.
What’s the car ride like after that? Silence, probably. But what about the motel? What’s the next thing they talk about together? How do you bridge that kind of silence?
How long did Dean stand there, staring at Brady’s body?
Did they salt and burn it?
Soooooo that's what Sam was up to when he turned 27! Cheery stuff.