The 10 Best Billie Holiday Songs You Should Listen To Right Now

Celebrating the music icon with some of my favorite songs.

Born Eleanora Fagan in 1915 to an absent musician father and a single mother, the Baltimore-raised jazz singer grew up in the fast life and never slowed down.

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In her 26-year career, Lady Day revolutionized jazz music and singing with her improvisational vocal style, which could flutter as lightly as Lester Young’s tenor and as intensely as Louis Armstrong’s trumpet, all in a single syllable. After she achieved mainstream success in the 1930s and 1940s with hits like “What a Little Moonlight Can Do” (with Teddy Wilson) and “Strange Fruit,” Holiday’s physical and mental health deteriorated in the late 1940s and 1950s, and she died in 1959 from cirrhosis at just 44 years old.

Along with innovative interpretations of jazz standards, Holiday wrote many of her own songs — a rare feat for jazz singers of that time.

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Langston Hughes said that the blues are “laughing to keep from crying.” Her voice conveys this paradox better than almost anyone else's, and in each smoky note, her insatiable appetite for life tangles with the terrible things life has done to her. Maybe the next hit, puff, drink, or screw will make things better.

I'm celebrating the diva's extraordinary talent with 10 of my favorite Billie Holiday songs, which are all as steeped in lore as she is. If you haven’t heard these songs before, grab a drink and take a seat:

1. "Strange Fruit"

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With lyrics written by communist poet Abel Meeropol (who adopted Julius and Ethel Rosenberg’s children), 1939’s "Strange Fruit" is undoubtedly the most influential track she ever recorded. The song paints a harrowing portrait of horrific lynchings juxtaposed against a Southern idyll, which renowned jazz writer Leonard Feather described as “the first unmuted cry against racism.” Not only did a song like this put Holiday in vocal opposition to racist retaliation, but no record label would touch it. The record was eventually released on Commodore Records after Holiday’s a cappella performance brought executive Milt Gabler to tears.

2. "I'll Be Seeing You"

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This sentimental jazz standard was written for the 1939 Broadway musical comedy Right This Way by Sammy Fain and Irvin Kahal, but it became a huge emotional hit during World War II, when families were lamenting the absence of loved ones fighting overseas. Holiday's arrangement with Eddie Heywood and his Orchestra in 1944 (the same year Bing Crosby took the song to No. 1 on the radio) may be the best-known version.

3. "Solitude"

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Perhaps my favorite Billie Holiday song, "Solitude" is a classic 1934 Duke Ellington composition that reflects on the loneliness of loss. As with many of her early recordings, the nostalgia of her words starkly contrasts with a breezy accompaniment.

4. "Blue Moon"

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"Blue Moon" has a rich history in American music, both at home and abroad. Written in 1934 by Rodgers and Hart and as a radio show theme, the record became a jazz standard after turning up in several MGM motion pictures and has been performed by everybody from Frank Sinatra and Rod Stewart to Ella Fitzgerald and Bob Dylan. Holiday's fantastic 1952 version is a standout despite the havoc that drugs and alcohol wreaked on her voice in her later years.

5. "Lover Man"

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This jazz standard is particularly associated with Holiday, who recorded it in 1941, the year she married James Monroe, an abusive playboy who was, as TLC would call it, a scrub. Monroe introduced her to opium, which set Holiday on her later path to heroin addiction (introduced by Joe Guy, another no-good musician she dated). Her 1958 live version is particularly haunting, paralleling her struggles to find a "lover man" who will treat her right.

6. "Billie's Blues (I Love My Man)"

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First recorded in 1936 with Artie Shaw and later in 1944 with Eddie Heywood and His Orchestra, "Billie's Blues," also known by the hook "I Love My Man," was Holiday's first copyright. Her first solo recording was largely improvised during the session, and since Bernie Hanighen had originally suggested that she sing a blues song, it became "Billie's Blues."

7. "Them There Eyes"

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Holiday is best known for her slow ballads, but let's not forget that the lady had rhythm. "Them There Eyes" is a big, swingy song with fun, catchy call-and-response band improvisations that make you want to do the Lindy Hop all night.

8. "All of Me"

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This is one of my favorite jazz standards of all time, and I love Holiday's recording with her lifelong friend and muse Lester Young. Holiday's definitive 1944 version is sadder than those of many of her peers — when she asks, "Why not take all of me?" it's a plaintive plea dipped in bittersweet memories, echoed by Young's effortless tenor. We've all been there, girl.

9. "Easy Livin'"

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Teddy Wilson tapped a young Holiday to sing vocals for this song in 1937, and the magical session included Young on tenor sax, Buck Clayton on trumpet, Walter Page on Bass, and Wilson on piano. Holiday's luxurious vocals weave effortlessly with their playing and capture the mood of a tie being loosened and a cigarette being sparked.

10. "God Bless the Child"

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According to her autobiography, Lady Sings the Blues, Holiday wrote this song after an argument with her mother about money. Holiday says that during the argument, her mother uttered the chorus’s inspiration: “God bless the child that’s got his own.” Writer Will Friedwald notes in his 1990 book, Jazz Singing, that the sacrilegious song heavily references the Bible as it points out how religion seems to have little effect in motivating people to treat one another better. The song won Holiday a posthumous place in the Grammy Hall of Fame in 1976.

What are your favorite Billie Holiday songs? Let us know in the comments below.