I got back into Borderlands 2 yesterday. I finished Hell Hath No Fury and Statuesque, and then went on to Toil and Trouble. Hearing Jack go right from making fun of Moxxi and complaining about me destroying his statues in Opportunity to hearing him talk about his vendetta against the Vault Hunters for killing Angel was jarring to say the least.
Also I had just started a playthrough of the Pre-Sequel where Jack is actually a decent guy (and a playable character) so I was jarred more by that.