Back at the motel, while Sam tends to a bleeding Gideon and Castiel is lying on one of the beds, still a little fuzzy from Leah’s attack, Dean takes the Impala and leaves. He drives all night and arrives the next morning at Lisa’s house. She asks him if he’s alright, and he admits that he’s not. He tells her that he wanted her to know that when he does picture himself happy, it’s with her and Ben. She’s shaken by this admission, and realises that Dean is about to do something stupid. She begs him not to do whatever he’s thinking of doing, and he tells her that he has to before leaving.
Michael Shanks guest starred in this episode (to the joy of SG1 fans, Pip in particular). He was, as always, quite fantastic and although it's probably not quite doable, I'd love to see him in another episode of Supernatural.
The title of the episode, of course, has to do both with the episode number (which is, you guessed it, 99), as well as a reference to Jay Z's song, "99 Problems" (although the chorus would have to be reworked somewhat to suit this episode).
When the Winchesters first walked into Blue Haven, I couldn't help but be reminded of the future Dean saw earlier in the season, in the episode “The End” (504). The visual reminder of what could be makes the march toward a bad ending seem all the more inevitable. Thank you, Julie Siege, for toying so with my emotions so.
I think I have been watching and analyzing way too many episodes of Fringe lately, because I couldn't help but wonder if the church's address (number 9160) has anything to do with, well, anything. It was just so prominent and stood out. I of course thought of the Bible. But where to look? Since I’m no Bible expert (I read it and have yet to understand 1% of it), so I’d love to hear from someone who is. J.J. Abrams, I blame you for messing with my head. I shudder to think of the consequences had I also been a Lost fan.
Castiel provided for sombre levity in a way that both suited the hopelessness of the character and that of the situation while staying true to the acerbic wit and humour of the series. First was his voicemail message (“You have reached the voicemail of…” “I don’t understand. Why do you want me to say my name?”). Then, of course, there was Drunk!Castiel whose drunken desperation is a poignant contrast to his previous seemingly unshakable faith in God. Misha Collins’ performance, enhanced by that of Jared Padalecki as a surprised yet still in control Sam and that of Jensen Ackles, as a not-quite-hopeless-but-getting-there Dean made the scene between the three of them (when Dean comes back to the motel to find Castiel there) priceless.