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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.

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