Thoughts on 99 Problems
When this episode opened with a high speed chase (featuring the Impala in all her glory and being wounded with a broken window) I thought we were in for an X Hours Ago to tell us the story leading up to the chase - not what happened. The heroes instead were saved by Sacrament Lutheran Militia and informed that "this is the apocalypse" (the truck and the group attack on the demons reminded me of Gunn's crew from Angel). The boys show their trunk full of demon hunting paraphernalia as proof that their hunters and on the same side. I found myself imaging the Impala tricked out like the truck, but I think the Winchesters are more subtle in their approach (and really, they're well known enough without an even more distinctive vehicle). As an opening, this was an effective attention grabber, no doubt. It was interesting to pick this episode up seemingly in the middle of a job and not let us know - did Sam pick up the amulet? I'm sure, nay, positive that he did but all the same, the curiosity is simmering here.
 
Castiel offered the macabre comic relief this week. As the cynical drunk who informed Sam of the "grating" quality of his "long" message he was humorous and helpful with research. How about the tone in which he identified himself as "an angel of the lord" to the priest - that had me chuckling. And who didn't enjoy the continuity of Castiel's ongoing struggle with the cell phone? I find it particularly interesting that it was Sam and not Dean calling Cas in the beginning. Call me over-analytical, but to me it testified to Dean's increasing and alarmingly passive attitude.  True that Dean did talk to Cas later, though Dean trying to perk up Castiel by comforting him and empathizing with the daddy-situation was too short a scene for me - I wanted a little more between the two of them. However, this was arguably the only moment in the entire episode where the old Dean shone through, even for just an instant - "you get to kill the whore" - he even had a little lightness to his expression as he said this.
 
The angels telling the whore that Sam and Dean are okay? Yup, that sent up a red flag. We, the audience, know that if the angels were truly speaking to this girl, allegedly a prophet, no doubt Sam and Dean would be blamed for the chaos that's going on or at the very least notified to Sam and Dean's whereabouts. I was surprised, before we knew she was the Whore of Babylon, when Leah was expressing the angel's commandments that she didn't inform the townspeople to capture Dean and Sam for the angels to nab. Very suspect "angel" behaviour.
The action sequence in the demon house was excellent. Sam was on fire with that knife and the SLM with their Enochian exorcisms? Awesome. "I guess that's what it's like, huh"¦having backup." Was I the only having ghoul flashbacks when Dylan was yanked under the car? This death seemed pointless; the demon didn't gain anything by drawing attention to herself in the presence of three hunters, so why bother? Panic and grief are always strong motivator, that's why. It was, after all, at Dylan's funeral that Leah had another "vision" and got information from the angels. 99 Problems was a perfect illustration of religious zeal at its extreme. How quickly these townspeople went from merely attending church on Sunday to murdering a neighbour in the name of Heaven - disturbingly referred to as 'the flock.'  It's always interesting to me that sinners are executed in the name of religion, but the sin of the execution itself seems to be okay. These townspeople are so blinded by their desire to please the angels that they can't see the incredible ridiculous of what they are doing - except for the priest, which is interesting. A person of true faith - the priest - is the only one able to recognize that God and the angels cannot possibly be delivering these messages to his daughter (even though the actions are in keeping with the Old Testament extreme).
 
The exchange between Dean and Leah was, quite simply, sad. The conflict and struggle was written across Dean's face plain as day. The idea of peace and family appealed to him but the weight of his guilt seems to be heavier than ever. Bad guys, for all their evilness, certainly have a way with words: "Must be hard, being the vessel of Heaven and having no hope."  
 
She wasn't the only one able to see Dean's turmoil. Sam's reactions to Dean's quips are typically amusement or exasperation, but not in this episode. His concern and increasing tension over Dean's lack of anything was lit up like a neon sign and he clearly didn't take Dean's comments to be jokes, but rather indicators of his mental state. The role-reversal between Sam and Dean in 99 Problems couldn't have been stronger. Dean staying in the hotel and Sam drinking? Sam getting chatty with the bartender? Whether it was meant to or not, this exchange inspired reminiscence of the pilot and the boys have switched roles even so far as this time, it is Sam standing and watching Dean leave without knowing where he's going or what he's going to do. If Dean says yes, and I do believe that is his intention at the end of this episode, he is further adopting the role Sam occupied last year - doing something (arguably the wrong thing) for the right reasons.
 
The agent of Heaven thing has certainly stirred up some debate. Personally, my motto with Kripke is to never take anything at face value. I believe that Dean could have killed the Whore at any point in the episode because he's been a servant of Heaven (meaning God and/or good, which doesn't necessarily include the angels like Zachariah) most of his life. Alternatively, the mere fact that he stepped out of passivity and up to defender of good in the moment he gripped the stake could have been all that was necessary. Another theory, which Robin mentioned, is related to the oath Dean made back at the end of last season - swearing to do serve Heaven. "Don't be so sure" - when Dean stakes the Whore he seems to be resolved in that moment, whatever revelation he had or decision he made then shook him out of his state of inaction - whether for good or bad, we can only speculate at this point.
This whole episode seemed to be about something bigger that itself. I felt as though many allusions were present throughout 99 Problems, from agent of Heaven issue to Dean's conversation with Lisa. One that particularly stood out was the moment when Dean killed Leah. It was painfully obvious that arrogance (on the part of the whore) was her downfall. She falsely assumed that not only couldn't Dean kill her, but that he wouldn't and that is why, she claimed, her side - meaning Team Lucifer - would win. The whore shouldn't have underestimated Dean - as he put it, "don't be so sure" - and perhaps this is demonstrative of the entire Team Lucifer. This isn't the first time this season that conceit and overconfidence in self has been present and likely it isn't the last. Pride, after all, is the sin of Lucifer.
 
The final moments of 99 Problems left me absolutely destroyed (which was in no way conducive to preparing for the exam I had Friday morning). The distress that Dean was feeling throughout last week and this episode reached its pinnacle here - and it's clear he's drowning. This town and the experience with its people solidified something for Dean and inspired him to a decision - which I'm fairly certain involved that "yes" word and donating his body for a heavenly test drive - it was the final push of a man already on the edge. The longer Lucifer walks free, the more souls are condemned to hell, something Dean knows about. When Dean walked into the hotel room after the bartender was shot, the image of him standing there with the violent red of the blood on his hands was a visceral allusion to Dean's headspace.
 
I'd almost forgotten that we'd seen Lisa in the Then segment by the time Dean knocked on her door. His confession has me reaching for the tissue, even in the rewatch: "I know the life that I live. I know how that's gonna end for me"¦but I wanted you to know that when I do picture myself happy - it's with you, and the kid." What an utterly terrible, tragic thing it must be to understand that you are going to die horribly and never be able to have the perfect, simple happiness you've longed for all your life. I'm glad that Lisa tried so hard to stop Dean and that she recognized he was about to do something extreme - he was able to see that she did care about him. I can't say that Dean was in love with Lisa, per say, or that she was his One, but rather she represented something for Dean - his perfect ideal of family and love. In saying goodbye to Lisa, Dean seemed to be accepting that he would never be able to have this life but the last thing he plans to do is barter her safety. Dean's actions remind me of a suicidal person - saying goodbye to loved ones and ensuring loose ends are tied up. The lines about choice - Dean arguing he didn't have one - seemed to be less about whether he could come in and have a beer and more about whether he had a choice to say yes or no to the Angels. Oh Dean, you break my heart.
 
Wish though I do, next week doesn't appear to offer any sort of reprieve from the emotional onslaught. Good news for the people at Kleenex, I suppose. Everyone have their tissue on hand for episode 100? It's going to be a doozy.