Miles Davis: Kind of Blue (1959) (listen to commentary)
The best-selling jazz recording of the era (and a perfect introduction for the jazz newbie), Kind of Blue helped introduce a new sound for jazz. Working from relatively simple structures, the musicians here lay out wonderfully lyrical extended improvisations.

John Coltrane: Love Supreme (1964) (listen to commentary)
One of Coltrane's most spiritually moving recordings, this disc has been popular among devotees and neophytes alike. It's a heart-felt celebration of divine love, with equal measures of devotion and exploration.

Horace Silver: Song for My Father (1963) (listen to commentary)
One of the first hard bop albums and also one of the greatest, and not just from that title track (honored in "Rikki Don't Lose That Number") but also his classic "Lonely Woman."

Dave Brubeck: Time Out (1959) (listen to commentary)
What was conceived by pianist Brubeck as an adventure into unusual time signatures ended up one of the most successful records in jazz history, due in large part to its beautiful melodies and the mesmerizing alto work of Paul Desmond.

Art Blakey & The Jazz Messengers: Moanin' (1958)
Jazz's most explosive drummer debuted his third version of the Jazz Messengers with this instant hard-bop classic. It's way too funky in here, thanks to compositions and performances by Benny Golson, Lee Morgan, and Bobby Timmons (who contributed the famous title track).

Ornette Coleman: The Shape of Jazz to Come (Atlantic, 1959)
Still controversial after all these years, Coleman jettisoned playing on chord changes – the basis of virtually all previous jazz improvisation – in favor of a freer, non-harmonic approach. This influential recording shocked many listeners in its day, and became the manifesto of the jazz avant-garde.