17 Sad Jazz Songs, The Saddest Ever

“Sentimental Journey” by Ella Fitzgerald

Song Year: 1947

Originally recorded by Doris Day, “Sentimental Journey” tells of longing for home. There’s some intimation in the lyrics that the narrator can’t seem to make it back there, though Ella Fitzgerald does sing about having a reservation for the next train.

As melancholy as the song feels, there’s every possibility she never makes the train home.

“Dark Was the Night, Cold Was the Ground” by Blind Willie Johnson

Song Year: 1928

Blind Willie Johnson taught himself to play the guitar at the beginning of the 20th century. He ended up learning to make sounds on the guitar that no one previously had and helped usher in the era of the guitar as a lyrical instrument.

“Dark Was the Night, Cold Was the Ground” was adapted from an 18th-century hymn, and Johnson added some call-and-response elements and others from African-American musical traditions. The lyrics detail the sorrow Jesus felt on the night before his crucifixion.

“It Never Entered My Mind” by Miles Davis

Song Year: 1960

The 1940 Rodgers and Hart show “Higher and Higher” gave us “It Never Entered My Mind,” a song about someone realizing that he’s lost his love, though it had never occurred to him that he’d end up alone.

Trumpet legend Miles Davis recorded this instrumental version in 1956, but it never saw the light of day until the release of “Workin' with the Miles Davis Quintet,” a 1960 album. Davis’ muted trumpet and Red Garland’s heartbreaking piano work make this song as sad as can be even without hearing the words.      

“Oh, You Crazy Moon” by Sarah Vaughan

Song Year: 1963

Tommy Dorsey made the first recording of Jimmy van Heusen’s “Oh, You Crazy Moon” in 1939. This ridiculously sad song went on to get sung by Sinatra, Mel Torme, and Wes Montgomery, to name but a few.

But Sarah Vaughan’s emotive, evocative voice does the song real justice. The narrator scolds the moon for promising a future with a love she no longer has.

“B Minor Waltz (For Ellaine)” by Bill Evans

Song Year: 1981

Bill Evans forever altered the landscape of jazz in general and jazz piano in particular. He had a gift for crafting melodies that didn’t need words to get their message across, and “B Minor Waltz (For Ellaine)” stands as a terrific example.

What’s the song about? Who knows? But it’s such a melancholy melody that you almost have to assume that the titular Ellaine has gone away and Evans is broken up about it.

Released posthumously, the song is one of the last great things the world got from the Bill Evans Trio.

“Don’t Be Sad” by Brad Mehldau

Song Year: 2010

Another tune that can evoke sadness without lyrics, “Don’t Be Sad” from Brad Mehldau (who has been the Next Big Thing in jazz piano for a few years now) paints sonic pictures that don’t really need words.

Steeped in church music as a kid, Mehldau crafts tunes and chord progressions reminiscent of hymns. With that kind of backbone to a piece of music, even the saddest melodies have some hope behind them.

“I Get Along Without You Very Well (Except Sometimes)” by Chet Baker

Song Year: 1956

A paean to broken hearts everywhere, “I Get Along Without You Very Well (Except Sometimes)” effectively conveys the feeling anyone who’s ever lost a true love knows: I have, for the most part, moved on and gotten over you, but there will always be little things that remind me of you.

When I see or hear them, I’m taken back to those first few moments of loss when I thought there was no way I could ever survive this loss.

We’ve all been there, and Hoagy Carmichael wrote this song, but Baker’s rendition stands as the definitive interpretation.

Sad Jazz Song, No.1 by l i l a · 2018

Song Year: 2018

If Mazzy Star were a young Canadian guitarist who sang lots of surrealist lyrics, that young Canadian guitarist would be named l i l a, and she would record “Sad Jazz Song, No. 1.”

This song is almost spookier than it is sad, and while l i l a considers herself more of a dark folk act, her chords and the voicings on her guitar evoke an undeniable jazz ethos.

Sad Jazz Songs, Final Thoughts

The power of music is unmatched when it comes to conveying emotion. After all, the Romantic composers of the 19th century explicitly sought to convey, through music, the non-conveyable. Jazz can do it just as well as any other form of music. These sad jazz songs are just a sample of the emotive might that music can wield.