[Don] Draper convinced his former bosses and some of his best--and often under-appreciated (by him)--employees to literally fly the coop in the middle of the night.Never mind that, as we saw recently, convince is really not the word to use in this context. And I give a pass on the split infinitive to literally fly--because, like all people of derring-do, I think split infinitives are pass-worthy. But propping up the limp cliche fly the coop by sticking a misused literally in front should get you 40 lashes with Ann Landers' wet noodle (to borrow a 60's-era term).
Literally, we should recall, indicates literalness. I saw the episode discussed and nobody was in a coop, and nobody sprouted feathers and took wing. (It reminds me of another passage I came across a while back in a video game review that said playing the game in question was "literally masturbation." Remind me not to use the controller after you, buddy.) To use literally when you're speaking figuratively is to disarm the word in the service of hysterical hyperbole. This is how many useful words die --not because of premeditated murder, but because of thoughtless "backing over the kid in the driveway" negligence.