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
Courtesy of Impulse! Records
Johnny Hartman sings “Lush Life,” Billy Strayhorn’s plaintive song of unrequited love and alcoholism, on the 1963 album John Coltrane and Johnny Hartman.
Download "Lush Life" single track.
2. ‘Lonely Woman’ - Ornette Coleman
Courtesy of Atlantic Records
You can almost hear a woman’s anguished cries in Ornette Coleman’s tone on this 1959 album, The Shape of Jazz to Come.
3. ‘Born to be Blue’ - Wes Montgomery
Courtesy of Riverside Records
4. ‘St. James Infirmary’ - Jack Teagarden
Courtesy of RCA
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.
5. ‘I Guess I’ll Hang My Tears Out To Dry’ – Dexter Gordon
Courtesy of Blue Note Records
Download "I Guess I'll Hang My Tears Out to Dry" single track.