Below are five jazz songs with depressing subject matter, for those who aren't feeling cheerful and brimming with love on Valentine's Day. Luckily, despite their focus on the blues, the macabre, or the mournful, these songs are beautiful and even strangely uplifting. Make sure to also read my Valentine's Day List of Jazz Love Songs and my Valentine's Day List of Jazz Songs of Lost Love.

1. ‘Lush Life’ - John Coltrane and Johnny Hartman

Johnny Hartman sings “Lush Life,” Billy Strayhorn’s plaintive song of unrequited love and alcoholism, on the 1963 album John Coltrane and Johnny Hartman.

 

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2. ‘Lonely Woman’ - Ornette Coleman

You can almost hear a woman’s anguished cries in Ornette Coleman’s tone on this 1959 album, The Shape of Jazz to Come.

 

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3. ‘Born to be Blue’ - Wes Montgomery

On the 1962 live album Full House, guitarist Wes Montgomery provides us with the meaning of the blues.More »

4. ‘St. James Infirmary’ - Jack Teagarden

For some reason, trombonist Jack Teagarden’s version of “St. James Infirmary” is included on The Complete RCA Victor Recordings of Louis Armstrong. It’s not clear why, but regardless, this is a great version of a morbid song about seeing one’s lover laid out dead in a hospital.

 

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5. ‘I Guess I’ll Hang My Tears Out To Dry’ – Dexter Gordon

Saxophonist Dexter Gordon gets vulnerable with this misty-eyed ballad on his 1962 album Go!.

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