First, there were some things I did like about this episode. Michael Shanks of Stargate fame did a great turn as one of the town residents, and actress Kayla Mae Maloney did a fantastic job as Leah Gideon/The Whore of Babylon. The acting from all the principals — Jared, Jensen, Misha — was damned great as well, considering what they had to work with. There were a lot of great little moments, like Sam saying Dean was the only thing he could count on and Dean showing how he’s further lost faith and hope. The fire truck scene in the beginning was also pretty awesome.
However, there was more about this episode that made me either scratch my head in confusion or that I just flat out disliked. It’s a shame too, the episode had such as strong beginning. The first thing I noticed is that, after killing all those demons with his knife, and having it still covered in demon blood, Sam didn’t even bother to notice. Hello, wasn’t that like, a major thing just a few episodes earlier? Didn’t he have to go through detox AGAIN? Now he’s cured? Seriously?
Secondly, when Dylan’s mother Jane looked at Dean and said that Dylan’s death was his fault, I totally cried out "bullshit!" Dylan died after a raid on a small demon stronghold in which the parents — Jane and Rob (played by Shanks) — BROUGHT HIM ALONG. There were guns, knives, and DEMONS, for chrissake. The chances of him getting killed during the raid were pretty damned good, so for her to blame Dean for Dylan’s death when she and her husband brought the kid along, to me, was ludicrous.
Thirdly, Castiel seemed nearly wasted in this episode. I can understand the anger and grief over hearing Joshua’s message from God to "back off," but this seemed a bit overkill. It seemed like Castiel was a shell, more there to do the brothers’ bidding more than any kind of independent character. I just felt less of a connection with him this time, and am wondering if they’re doing that purposefully or if it’s just bad writing of the character of late.
Next, the scene with Lisa at the end…what the Hell was up with that? Dean sleeps with a girl once, visits her again over a decade later, and suddenly she’s the love of his life? I didn’t think Dean HAD a love of his life, but Lisa I can kind of understand…because she’s hot and all. 😉 Another thing that bugged me about that scene is…where’s Lisa’s current significant other? A girl that pretty without a boyfriend or a husband? Seriously? I mean I can see if she didn’t want one or need one, but the absence of one was palatable. Was she still pining for Dean after all these years because of a single one-night stand? The scene between her and Dean felt kind of touching, but forced overall.
Finally, other little things bugged me. What did the title, "99 Problems" mean? Was it because this was the 99th episode? Were there only 99 people in this town? Someone told me this was the same town that Pastor Jim — an old Winchester friend who was killed a while back — was from…yet no one knew of him or mentioned him? Seemed a bit odd.
Overall, this was a setup episode, I think, to Dean saying yes to Michael in the big 100th episode next week. That’s a guess on my part, by the way, not anything spoilery (because I haaaaaate spoilers). This will ultimately be one of those forgettable episodes that, while in the minority of the series as a whole, won’t be one anyone will need to watch again.