Miles Davis - Sketches of Spain
I was wondering when we'd get to a jazz record on this list, and though I'm kind of surprised that Sketches of Spain is the first one to pop up here, I think it's a good choice. Regardless of your feelings on jazz or Miles Davis this is a musical masterpiece. Sketches of Spain transcends genres and expectations. It plays more like a classical work or a soundtrack than a jazz album. That said, if this ends up being the only jazz album Esquire includes, I'll be annoyed.