Most artists are lucky to help define a single era—this innovative trumpeter did it four times. In the late ‘40s, he helped codify the cool jazz approach to bebop thanks to his light-touch solos over fast chord changes. In the ‘50s, his quintet with John Coltrane recorded Kind of Blue—a modal jazz milestone that announced a less frenetic but equally profound style. His sultry big band works of the ‘60s and rock-tinged fusion albums from the ‘70s are as different as they are exciting. Whether playing soulful romances or inspiring funk jams, he was a visionary.