This is an album I like to listen to on my headphones when I look like the sort of guy who'd be listening to almost anything else. It makes me feel cooler than any of the people around me would assume I am. Miles Davis truly was the king of cool (more cool than peeing your pants, if you can imagine) and if you're walking around with "Freddie Freeloader" bopping around in your headphones you feel like the coolness is rubbing off on you. You can't like jazz and not like this album. It's as simple as that.