Jazz can be a truly joyful musical experience, and it can be almost as much fun for the listeners as it is for the players. But any art form that can uplift us like that can do the opposite just as effectively.
Here are some of the best sad jazz songs from some of the biggest names in the genre.
“Strange Fruit” by Billie Holiday
Song Year: 1939
Based on a poem songwriter Abel Meeropol wrote a few years earlier, “Strange Fruit” is one of the darker songs in the jazz genre. Though acts as diverse as Nina Simone, Siouxsie and the Banshees covered it over the years, Holiday’s version remains the definitive one.
With its graphic description of the aftermath of racially motivated vigilante violence, the song stands as a brutal depiction and damning portrait of lynching.
Unsure of the content? The strange fruit is the bodies of murdered African-American men hanging from the trees in the American South.
“Lush Life” by Billy Strayhorn
Song Year: 1948
Strayhorn wrote the joyous “Take the A Train,” but he also wrote this dizzyingly sad portrait of the emptiness that a pleasure-seeking lifestyle can leave one feeling.
The narrator thinks back on his nighttime adventures, but rather than feeling happiness, he realizes that he’s missed out on meaningful connections with people and has yet to experience a fulfilling relationship.
The wordplay of the title revolves around “lush” as an adjective meaning rich and luxurious and the pejorative noun meaning of the word— a drunk.
John Coltrane covered the song in a seminal recording, but a little of its sadness is lost without the lyrics.
“A Certain Sadness” by Astrud Gilberto
Song Year: 1967
Astrud Gilberto became a huge star in the 1960s when she sang on Antônio Carlos Jobim’s “The Girl from Ipanema.” Her lovely voice took her places in the jazz and bossa nova worlds, and when she recorded her 1967 album, “A Certain Smile, A Certain Sadness,” she included “A Certain Sadness as the album’s second track.
Like so many sad songs, it tells of lost love, but perhaps most striking is when she sings about how much she loves looking into her love’s eyes, but he refuses to look at her anymore. She ends the song voiding the fear that this particular sadness won’t ever go away.
“The Ballad of the Sad Young Men” by Anita O’Day
Song Year: 1962
The saddest part of “The Ballad of the Sad Young Men” isn’t the ongoing description of what seems to be a generation of guys who’ve lost their way, but rather the fleeting reference to the sad young girls who try to pretend everything will be fine.
O’Day does a great job emoting in this one. Even if you didn’t understand English, you can still hear that she’s singing something sad.
“Almost Blue” by Chet Baker
Song Year: 1989
Elvis Costello wrote “Almost Blue” with Chet Baker in mind, so when Baker himself covered it, it was something of a full-circle moment. Baker, known for his ability as a trumpet player, was also a gifted jazz singer, which helped after he was beaten up in 1968— badly enough that his embouchure never recovered, so he never played the trumpet as well again.
The narrator, singing to a lost love, tells her that the one he’s with now is almost her. That’s depressing, man.
“A Stranger in Town” by Mel Torme
Song Year: 1961
Something about Torme’s voice lent the possibility of sadness— or at least melancholy— to anything he sang. But “A Stranger in Town” has sad lyrics to go with the aching in Torme’s voice.
The narrator finds himself not a stranger in just any town, but in his hometown. He steps off the train to notice that everything has changed, and life has moved on there without him.
“I Guess I’ll Hang My Tears Out to Dry” by Frank Sinatra
Song Year: 1946
Sammy Cahn and Jule Styne wrote “I Guess I’ll Hang My Tears Out to Dry” for a 1944 musical that flopped before it reached Broadway. But its authors wrote a well-crafted song, doing things like rhyming “alibi” with “out to dry.”
Sinatra put his pipes to this one in 1946 and wove the sad tale of recalling a lost love and wallowing in the sorrow of doing so.
Saxophone legend Dexter Gordon played an instrumental version that’s every bit as emotive as what Sinatra did, and Gordon did it without words— just with his sax.
“To Say Goodbye” by Paul Desmond
Song Year: 1969
Brazilian legend Elis Regina lent her stellar voice to Desmond’s haunting version of “To Say Goodbye.” Though Desmond is widely known for his intricate and virtuosic work with the Dave Brubeck Quartet, this tune, recorded for Desmond’s solo album “From The Hot Afternoon,” showed off a softer, mellower side.
His alto saxophone tone is sad enough without Regina’s vocal work. Together, they make a really sad song.
“Gloomy Sunday” by Billie Holiday
Song Year: 1941
Originally sung in Hungarian, “Gloomy Sunday” was called “Vége a Világnak,” which means “end of the world.” It was written by Rezső Seress.
Billie Holiday’s version, with English lyrics, came to be known as the Hungarian Suicide Song, and it was so sad that, during WWII, the BBC banned it from its airwaves due to its deleterious effects on morale.