There is almost universal agreement that Billie Holiday is the best pop singer in history. One might argue with the term “pop”. Her music was called jazz during her career, but jazz was the popular music of the day. One could certainly take issue with the word “best” because Lady Day did not have the largest vocal range, sweetest timbre, or even most resonant vibrato. Attending to any individual category, one could always come up with vocalists who were superior to Holiday in discrete ways. And I don’t mean female vocalist — just vocalist. Frank Sinatra may be grand, but even the Chairman of the Board admitted Holiday’s talents exceeded his own. As a whole, there have been none better. Everyone is entitled to one’s own taste, but it cannot be denied that the consensus of musical opinion crowns Lady Day as the greatest ever.
Many fans and critics consider the music on these three discs, dated from 1935 to 1939 when she first signed to Brunswick Records, the cream of Holiday’s recordings. That’s debatable, but no one would dispute the value of this material. Lady Day was only 20-years-old in 1935. She discovers how to match her voice to the technology, how to sound distinctive (despite record company pressure to imitate the prevailing women singers), and how to jam vocally with great players such as pianist Teddy Wilson and tenor saxophonist Lester Young.
Many of these songs have become part of the Great American Songbook and have been covered by too many musicians to count. Some of these may have been hits for others at the time, but Lady Day made them her own with her idiosyncratic intonations, and precise phrasing combined with a unique voice that simultaneously conveys joy and heartache. Consider her take on the Jerome Kerns/Dorothy Fields composition “The Way You Look Tonight”, originally recorded by Fred Astaire for the movie Swing Time. Holiday lets the song sizzle instrumentally before joining in, and even then seems a bit reluctant as if to brag about her good fortune of seeing things through the eyes of love acknowledges that the feeling won’t last. Indeed, there is nothing for her but to love, as she sings. The ephemeral nature of the moment is heartbreakingly perfect. The song drips with emotionalism, but Holiday expresses something more transcendent than sugar.
It’s the magic of her voice. There is no rational explanation for an artist of Holiday’s caliber. She can turn a silly ditty such as “Yankee Doodle Never Went to Town” and turn it into the swingingest party that there has ever been (“He didn’t even have a pony,” she smirks with a wink), or a piece of pap like “These N That N Those” into a seductive ode to physical embracing. She transcends the material, and despite aiming for hit records more than artistry, she creates art of the highest caliber.
Consider Lady Day’s versions of “Pennies from Heaven”, “Nice Work If You Can Get It”, “The Way You Look Tonight”, and “Mean to Me”. She transports the listener to a higher plane of consciousness through her singing. This may seem crazy, but it doesn’t take a lunatic to appreciate Holiday’s performances. Just check out the five lunar-themed tunes on this collection: “What a Little Moonlight”, “What a Night, What a Moon, What a Boy”, “It’s Like Reaching for the Moon”, “I Wished on the Moon”, and “Let’s Dream in the Moonlight”. Lady Day rhapsodizes about the night and romance. The frisson caused by the bright object in the dark sky complements the rough and smooth characteristics of her voice. You cannot have one without the other.
So is this the one Holiday collection to buy if you are only buying one? No, but the truth is you shouldn’t purchase just one. You should get everything Holiday ever recorded no matter how raggedy the recordings or her voice may sound. This three-CD set showcases Holiday at her freshest, with top notch players and many fine songs. That should make its acquisition into your collection an easy choice.