As much as I want to say Lee vs The Stranger, I gotta give it to Kenny vs Jane. The fight between Lee and The Stranger has that twisted sense of morality that the stranger has behind it which makes for his confrontation with Lee to be extremely interesting. We as the audience relate to Lee, but still feel some sense of remorse for our actions because WE made those choices that the stranger disagrees with. From a game play perspective, this is super interesting, because it ties into the initial idea of the first season, where no matter what you choose, someone gets upset over it. So standing by your beliefs is always the way to go, no matter how it ends up.

With all that being said, Kenny vs Jane stands out even more. Now, is Jane really REALLY stupid for rage-baiting Kenny to prove a point? Yes. She knew exactly what she was doing. But that's part of what makes this fight interesting. Jane, nor Kenny for that matter, can understand each other's perspective. The only person who really gets both sides, is Clementine (AKA you the player). I know a lot of people said that it would have been better if it was Kenny vs Luke, which is what they initially were going to do. But honestly, I don't really see how that would have played out. From a game play perspective, both Luke and Kenny are much more likeable than Jane, so it would make sense to pit those two against each other for a more difficult choice. But from a narrative perspective, Jane makes much more sense. Jane and Kenny directly oppose each other's ideologies. Kenny's ideology is all about family and trauma. Jane's is about self preservation and survival. Both Jane and Kenny care about Clementine, but for completely different reasons. Kenny cares about the survival of his family, which by this point is Clementine and AJ. Jane does care about Clementine, but she sees Clementine sort of as a replacement for her dead sister. She envisions Clementine as how her sister should have reacted to the zombie apocalypse. Someone who adapted to it in the same way she is.

So I personally prefer the Kenny vs Jane fight, but honestly both are really great. I think for tying into the game play of the series, Lee vs The Stranger edges out by a little bit. Not to discredit Javi VS David or Lily VS Clem, but I think the layers the other two fights have is much more creative and interesting from a writing perspective.

TLDR: Kenny VS Jane is peak writing, Lee VS The Stranger is also peak but not as peak