1. "West End Blues," Louis Armstrong and His Hot 5

Nearly everything rad about jazz is packed into these three minutes recorded in Chicago on June 28, 1928. With its unaccompanied 12-second opening trumpet statement, Armstrong's scatting duet with clarinetist Jimmy Strong and a gloriously held B-flat in the final chorus, Armstrong launched a musical Apollo mission whose reverberations are still being felt today. 

2. "A Sailboat in the Moonlight," Billie Holiday and Her Orchestra

Jazz's most influential vocalist could transform even the tritest of tunes into something special. The brilliance of this 1937 track lies in her laid-back reading of its lyrics and the silky conversational repartee provided by her musical soul mate, the magnificent tenor saxophonist Lester "Pres" Young.

3. "Take the 'A' Train," Duke Ellington Orchestra

The Ellington band's 1941 recording of Billy Strayhorn's iconic composition departs the station with piano flurries suggesting a train horn. Its swinging elegance radiates an optimistic sense of social mobility — at least if you were fortunate enough to live in Harlem's upscale Sugar Hill neighborhood — and embodies the artistic savoir faire that was Ellington's specialty.

4. "Embraceable You," Charlie Parker Quintet

Shortly after his discharge from California's Camarillo State Mental Hospital in 1947, the bebop alto-sax icon recorded one of the more renowned balladic performances in jazz history. His roller-coastering two-minute interpretation of the George and Ira Gershwin classic sets the stage for 21-year-old Miles Davis's short, sharp trumpet solo.

5. "Brilliant Corners," Thelonious Monk

The rhythmically knotted, melodic twists and turns associated with this pianist's compositional genius are on full display in the title track of his first great album, recorded in 1956. Tenor sax colossus Sonny Rollins lays into his solo with passion and authority on a tune so difficult to play that it was sutured together from different takes.

6. "My Favorite Things," John Coltrane (1960)

Jazz brims with wonderful reinventions of Broadway tunes, but few are as remarkable as this spiritual jazz giant's 1960 recording of a Rodgers and Hammerstein gem. Coltrane (on soprano sax) and pianist McCoy Tyner vamp transcendentally over two chords on an extended slice of bliss whose edited version became a hit single. 

7. "Filles de Kilimanjaro," Miles Davis (1969)

More mystic séance than mere recording session, the title track of a thoroughly satisfying 1969 album offers a master class in cool from the trumpeter who embodied it. With its exquisitely pulsing electric keyboards, telepathic interplay and a laid-back sense of trouble brewing, Filles foreshadows the high-voltage rock sound Davis would introduce a year later on Bitches Brew.

8. "Civilization Day," Ornette Coleman (1972)

Jazz rarely sounds as blissfully caffeinated as in this manic blast from Coleman's 1972 masterpiece, Science Fiction. The alto-sax-playing dervish and his longtime trumpet partner Don Cherry front a quartet that makes an irrefutable artistic point about the raw power of jazz — even in the age of rock. 

9. "What Are You Doing the Rest of Your Life?" Sarah Vaughan with Michel Legrand (1972)

A singer of unique emotional breadth and technical depth, Vaughan made a big splash alongside Clifford Brown in 1954. By 1972, when she recorded this bittersweet ballad with composer Michael Legrand's orchestra, her voice had assumed operatic dimensions. Stick around for her final note and tremble with awe.

10. "Human Nature," Vijay Iyer Trio (2012)

Pianist and MacArthur “genius” Vijay Iyer transforms Michael Jackson's pop gold into modern jazz platinum with his mighty trio featuring bassist Stephan Crump and drummer Marcus Gilmore. This 2012 interpretation builds up to a powerful climax and then breaks like a wave into something subtly sublime.

—Richard Gehr