If I got to pick any "job" in history it would definitely be that of a swashbuckler. I mean think about all the cool things pirates get to do - sword fight, ride on ships, drink rum, visit cool places, watch the sunset over the ocean, etc. I mean, yeah, life expectancy wasn't that great and I don't even want to think of all the diseases a pirate had to deal with. But hey why not have a little fun before you leave this earth, am I right? The great scene below by Brother Steven and his brother Mark is exactly what I'd expect the life of a pirate to be.