From Billie Holiday to Miles Davis: 8 Timeless Covers of Classic Jazz Songs

By: Shelby Jefferson April is Jazz Appreciation Month, a time to celebrate a musical genre deeply embedded in the fabric of the American soundscape. As part of a long tradition, jazz artists often perform varying interpretations of songs recorded by other musicians. Still for many fans, certain renditions will forever reign as personal favorites. Whether you’re a jazz aficionado or a novice listener, here are eight awesome covers to round out the perfect playlist for any music lover. Song: “You Go to My Head” Original Artist: Teddy Wilson and His Orchestra featuring Nan Wynn (1938) Shelby’s Favorite Cover Version: Billie Holiday (1938) “You Go to My Head” has been performed by a number of jazz greats, but Billie Holiday’s emotive sound and superb vocal phrasing, paired with the romantic sophistication of the song’s lyrics, make this the crème de la crème of all existing renditions. As we continue our centennial celebration of her timeless sound, Lady Day’s take on this pop-jazz standard further validates her place as one of the most influential vocalists of all time. Song: “Naima” Original Artist: John Coltrane (1959) Shelby’s Favorite Cover Version: Pharoah Sanders (1987) “Naima” was first recorded as a loving ode to John Coltrane’s then-wife Juanita Naima Grubbs. Nearly three decades after its release, saxophonist Pharoah Sanders skillfully blends the ballad's slow, evocative arrangements with elements of free jazz in an expressive tribute album to the iconic “Trane”— with reverent, serene vibes sure to bring out the inner romantic in any listener. Song: “Watermelon Man” Original Artist: Herbie Hancock (1962) Shelby’s Favorite Cover Version: Mongo Santamaria (1963) During a memorable jam session at a Cuban nightclub, guest piano player Herbie Hancock — joined by Mongo Santamaria and his band — broke out with an impromptu performance of his blues-centered masterpiece “Watermelon Man." Months later, Santamaria recorded a new version of the tune, incorporating jazz, R&B and Afro-Cuban percussion to produce a Top 10 hit on the pop charts in 1963. Song: “Good Morning Heartache” Original Artist: Billie Holiday (1946) Shelby’s Favorite Cover Version: Chris Botti featuring Jill Scott (2005) Doing justice to a Billie Holiday classic is no easy task, but Chris Botti and Jill Scott manage to do just that in this lovely cover of “Good Morning Heartache." It can be said that Scott’s vocal performance never truly reaches the full altitude of pain and loss imparted by the great Lady Day. Nevertheless, her resounding soprano — supplemented by Botti’s soft, melodic grooves on the trumpet — bring a contemporary feel to this timeless jazz treasure. Song: “Round Midnight” Original Artist: Thelonious Monk (1944) Shelby’s Favorite Cover Version: Miles Davis (1957) “Round Midnight” is regarded as the most-recorded standard ever written by a jazz musician. In this unique interpretation, Miles Davis — joined by a stellar band that became known as the First Great Quintet — reads the song’s harmonic beauty with a muted trumpet in an exquisite performance for the ages. First debuting at the Newport Jazz Festival in 1955, Davis’ take on Thelonious Monk’s eternal work of art indisputably ranks among the most definitive versions of all time. Song: “Endangered Species” Original Artist: Wayne Shorter (1985) Shelby’s Favorite Cover Version: Esperanza Spalding featuring Lalah Hathaway (2012) Renowned saxophonist Wayne Shorter first composed “Endangered Species” as a catchy instrumental filled with '80s funk vibes and electronic rhythms. In comes Grammy Award-winning bassist/vocalist Esperanza Spalding to revamp the track in 2012 — adding original lyrics to the composition about environmental abuse and its looming threat to Mother Earth. Lalah Hathaway’s sultry vocals easily ride the soprano sax section, while Spalding’s angelic voice perfectly enhances her pulsating genius on the bass. At the end of the day, this fly, groovy cover undeniably demonstrates that jazz music is indeed still alive in the 21st century. Song: “Breezin” Original Artist: Gabor Szabo (1971) Shelby’s Favorite Cover Version: George Benson (1976) Hungarian guitarist Gabor Szabo first recorded this Bobby Womack-composed tune in 1971. Five years later, George Benson revived the smooth guitar-led track as the hit title song to his album "Breezin" — a landmark LP that ultimately peaked at No. 1 on the jazz, pop and R&B Billboard charts. Song: “Afro Blue” Original Artist: Mongo Santamaria (1959) Shelby’s Favorite Cover Version: Robert Glasper Experiment featuring Erykah Badu (2012) In 2012, Robert Glasper Experiment teamed up with songstress Erykah Badu to fuse facets of jazz, neo soul and hip-hop into a new millennial interpretation of “Afro Blue.” Polished and atmospheric, the song’s distinctive flutes and intricate piano chords, paired with its hip and sweepingly soulful grooves, are sure to leave even hardcore jazzheads jamming to this innovative rearrangement of a Latin jazz standard released more than 50 years ago. Shelby Jefferson is a blossoming journalist. As a radical intellectual, writer, poet and pop culture junkie, she frequently uses her articles to analyze and present a broad spectrum of themes including race and representation in television/music/film/media, contemporary arts and culture, race and gender identity in sports and social justice issues in the United States.

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