5.14 "My Bloody Valentine"
Yay! I actually got to watch this episode live because the husband and I are all caught up. (Well, technically off the DVR and delayed by an hour, but close enough.)
I feel like this episode is what's great about this show. Ben Edlund. I'm kidding, mostly. Ben Edlund certainly helps with the awesomeness, but this one felt like a group effort. This episode started out looking like a cutesy (as cutesy as monsters and demons can be) Valentine's Day one-shot, with practically a full on vaudeville routine between Sam, Dean, Castiel, and the cupid, and by the end it was dark, painful, angsty, depressing and completely arc significant. Very much like "Monster at the End of This Book" which is definitely one of my favorite episodes. I guess I appreciate a good fake out.
It probably needs a few more watchings, but I can definitely see this episode being up there among my favorites. It has a lot of great dialog (tons of which I want to quote, but I'll refrain), hilariously deadpan Castiel, Sam in bondage, demon-blood-drinking-evil-Sam, Sam and Dean in suits, and Dean crying. The only thing really holding it back is how intolerably disgusting Famine is to look at. But even that works in the episode's favor, as he wouldn't be near as scary if he wasn't so gross. Plus it pretty much goes along with the grossness of people shoveling food into their mouths through the whole episode.
Okay, I can't resist just one quote: "Is this a fight? Are we in a fight?" That line is so straight up Whedon that I can actually hear it in Sarah Michelle Gellar's voice. Guess Dean really is Buffy Summers.