One of the most influential jazz trumpeter of all time (and in the running for most prolific), Miles Davis defined and redifined various permutations of jazz music throughout his 50-year career. A product of the Juilliard School, Davis got his start with Charlie Parker. He went on to create a titanic body of work that would make him a legend in his own time, earning him nine Grammy Awards, quadruple platinum certification for Kind of Blue, and a place in the Rock and Roll Hall of Fame.

Though it took the world the better part of a decade to recognize it, Thelonious Monk is heralded as one of the finest and most original jazz pianists ever to come out of New York. It wasn't until a 1956 gig with John Coltrane that Monk transitioned into life as an A-list jazzer. That pivotal performance led to extensive touring, a spot on the cover of Time in 1962, and recognition for the songs he wrote, many of which (including "'Round Midnight") became jazz standards after Monk's abrupt retirement in 1973.