Taking on Lily Orchard's 50 Sympathetic Villain Challenge

Awhile back, Lily Orchard (I'm sure you're excited to hear that name again on this channel) told her audience to name 50 sympathetic villains. So naturally, I and @thecrimsonender decided to call Lily's bluff. We each came up with a list of 50 sympathetic villains (Crim while rolling out of bed and I while in the bathroom) that Lily hasn't shut up about in the last three months, to the point where her next video is about it.
So we decided to review our list and see if they hold up. Also, we asked @SaiScribbles to judge/roast us.
Thumbnail art @thecrimsonender