Athough it didn't make me cry as much, the ending for s2 was actually sadder than the s1's.
For all the tragedy of the Season 1's ending - the theft of the boat, the death of Benny, the (then believed) death of Kenny, the impending death of Lee, Omid and Christa getting split from Lee, Clem seeing her dead parents and the goodbye scene - the whole story still had a felling of redemption to it: The group united against the Stranger who, despite probably having being an normal and decent person in the past, was then a vengeful psycho and a pretty unambiguous villain type. Lee had his time counted, but what he did with it was to put one hell of a last dance, he went out with a blaze of glory and his sacrifice saved Clementine, heroism. Even the part where Clem sees her dead parents had a happy element in it, for provided Clem with closure. And even the Goodbye Scene had a happy element to it for it gave Lee and Clem a chance to share some last moments together and Lee could prepare Clem for what's to come.
Season's 2 however was downright nihilist. There was no villain, just jerks and broken people. The group simply couldn't keep together, couldn't stop bickering over everything; My Clementine tried to stop every unnecessary conflict, but she wasn't listened to at absolutely any point at all, the only other character who had a chance to be the voice of reason on matters was Luke and he was the first one to meet a tragic end. Kenny scapegoated his anger on other characters at every chance he could, like he aways did since season one, he couldn't deal with loss and it took Lee a monumental effort to even make him accept the fact his son was dying and that was the type of effort that neither Clem nor anyone else in that group could pull off. Then comes Bonnie and Myke, the two characters we all had our hopes up for, turn out to be a pair of selfish backstabbers who can't put up with Kenny but think it's totally okay to steal the truck he fixed and leave him and Clem for dead. And Jane, she became afraid of being attached other people yet she comes around and decides not to be alone anymore, what she gets for it is seeing one of the only two persons she cared about in the group die. In the end, when shit starts hitting the fan she could have just left again, but she goes through with her decision this time and she is willing to kill Kenny in order to (what she view as) save Clementine. In the truck she shows sadism, pokes Kenny about his family and about how nobody trusts him anymore, she is clearly trying to make him go mad and this culminates in the scene where she outright leads Kenny to believe that she killed the baby. Jane knew she couldn't just murder Kenny in cold blood right in front of Clem, but she knew that she could taunt him into attacking her and she though she would come out victorious in a fight against him. The result was disheartening, after all that Clementine went through she is forced to watch the two last persons she has left fight to death. In my Clem's own words: "We are all there is left, we shouldn't be killing each other."
In the end I let Kenny kill Jane because I had grudge about she aways wanting to just let Sarah die, but it was an hard choice; one of the hardest I had in this game so far.
And in the end what was all this for? That baby? What did they even saved him from when the greatest danger around came from the group itself? And why should we even care about him to begin with? He is the child of a woman who was a huge asshole to Clem with (on the best scenario) a big fatass that didn't do shit the whole season or (on the worst scenario) the most malevolent and insufferable character in the whole season. He is nothing but an empty burden and if anything I would leave him for dead just for the off chance that I did be ridding the world of that last little bit of Carver. After all the meaningless violence that happened Clem's survival still felt empty, everyone she knew and cared about was dead except for one and this one person couldn't even go with her inside Welligton which was her last hope for security and the resemblance of a normal life, but very likely is just another illusion of such...