4. Billie Holiday and Lester Young

Billie Holiday (left) at the Downbeat club, a jazz club in New York City, in 1947. Portrait of Lester Young (right) at the Famous Door in 1946. Images by William P. Gottlieb from the Library of Congress 

The connection between iconic jazz singer Billie Holiday and saxophonist Lester Young certainly isn’t an anomaly, as they came up right around the same time in the New York City jazz scene. But it’s mildly surprising how deep, lasting, and platonic their friendship was. Young and Holiday first met in jazz clubs around New York City such as the Lenox Lounge and eventually the Apollo theatre starting in 1934– the year Young moved to the city to join Fletcher Henderson’s group. That same year, Young moved in with Holiday into the Harlem Hotel when a rat was discovered running around his Harlem apartment. From that moment forward, their friendship took off in a way that was “publicly recognized during their lifetime.” It would be Young who coined the popular epithet for “Lady Day,” and then Holiday who would give Young his nickname “Prez.”

Together, they created some of Holiday’s earliest hits including A Sailboat in the Moonlight. This session, according to mutual friends and producer George Avakian, “is really the one that expresses their closeness musically and spiritually more than any other.”

Holiday and Young rose together, but would also unfortunately fall together as they both went on to fight insurmountable battles against drug and alcohol addition. The musicians died just two months apart in the summer of 1959.