1) Michael Scott, THE OFFICE: Sure, he’s insane. But he’s also wildly easy to manipulate. “Hey, Mikey, wanna hit a bar for lunch and some mano-e-mano bonding?”
2) Angela Bower, WHO’S THE BOSS: Come on, how many times did you actually see Tony do anything even remotely “housekeeper”-like?
3) Charlie Townsend, CHARLIE’S ANGELS: Who doesn’t love the idea of a boss who never, ever shows up at the office, instead communicating entirely via telephone?
4) Col. Sherman T. Potter, M*A*S*H: Never was there a man who had more compassion for those serving under him, nor one better prepared to practice everything he preached.
5) Lorelai Gilmore, GILMORE GIRLS: Given the personal traumas she experiences on a weekly basis, no boss would be more sympathetic to whatever excuse you come up with upon arriving late each day. 