40. Miles Davis, Kind of Blue (1959)
Miles Davis is known for revolutionizing the jazz genre, not one but three times. This has to be the coolest records out there. In financial terms, Kind of Blue is his most valuable record.
Kind of Blue was recorded by legendary saxophonists Cannonball Adderley and John Coltrane, bassist Paul Chambers, Pianists Wynton Kelly and Bill Evans, and drummer Jimmy Cobb. An original of this classic can go up to $1,000.