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.
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.