It does come off as forced in a lot of places. Did a mission recently where i had to secretly follow a character into a secret cave and the whole time he's walking he's all "i can't wait to get to my stash and be myself where no one will ambush me and try to hurt me while i count all this cash with no one around all by myself...Hope no one's following me right now" Real dumb
Another great example of how humor is contextual. I absolutely love that, especially how how he compared himself to his dead brother. His best quality over him being that he was not currently buried in a shallow grave.