25 Coolest Jazz Artists and Singers

Here's my first crack at listing the hippest of the hip—and clips that make my point

Cool is a funny thing. You can’t really define it, and the word has no real synonym. Yet you know cool when you see and feel it. If I were taking a stab at a definition, I’d say a jazz artist who made excellence look easy, was understated, wasn’t a follower (or advanced whatever he or she was following), didn’t work hard at hipness, had enormous charisma, and established his or her own artistic vision. [Photo above of Lester Young and Miles Davis]