Let's say that Jackie dies a few years early or something, because unless ASBs tinker with his personality he won't openly defy her. So, let the discussion begin.
The Draper role is basically the opposite of his RL persona, but it would be amusing if nothing else.
Not seeing that. We've discussed a few TV series, what about movies? I didn't want to overly restrict the OP but that is what I hoped to be the main focus of discussion. Some Shakespearean movies would definitely be on the table because that was his specialty in the Brown acting club, and by all accounts he excelled. Perhaps Bossanio in TMOV? Pericles in PPOT?
War movies? Maybe Private Ryan?