Recently it occurred to me that its been a long time since I’ve heard a new song that is really sad. I’ve encountered plenty of new music that is perverse or aims to be shocking, but not anything that I would categorize as truly sad. And by that I mean the kind of song that has the capacity to create a genuinely sorrowful mood through its lyric and, of course, a melodic structure that reinforces the lyrical theme. This got me to thinking about the saddest songs I know, so here is my top ten list of saddest songs. Obviously, this sort of thing is somewhat subjective. A song that makes me sad might not hit you the same way. But there is also an objective component—attributes which explain why certain songs tend to prompt a melancholy response in listeners. I’ve highlighted some of those features in many of the songs in my list.

But first, here are ten honorable mentions:

  1. Both Sides Now by Judy Collins – A poetic, somewhat stream of consciousness reflection on how personal maturation inevitably involves loss and the discovery of one’s limits. Collins’ vocal is direct and plaintive, supported by rich orchestration. Joni Mitchell’s more spare and intimate original version is also wonderful.
  1. Cats in the Cradle by Harry Chapin – The ultimate song about parental regret over time and opportunities squandered. Our kids grow so fast, and before you know it they’re off to college. Not only that, but the song captures the sorrow of seeing your own faults recapitulated in your own kids: “…and as I hung up the phone it occurred to me, he’d grown up just like me. My boy was just like me.” Ouch.
  1. Those Were the Days by Mary Hopkin – A reworking of an old Russian melody, matched to a nostalgic lyric, Hopkin’s vocal performance is both precise and mournful. The history of art is replete with the pangs of sorrow over human mutability and our inevitable demise. This song captures and conveys that sorrow as well as anything I’ve heard.
  1. Yesterday When I Was Young by Roy Clark – Another song about nostalgic regret. Clark’s vocal performance isn’t particularly great, but the lyrical genius makes up for that. For some other versions with more compelling vocals, check out this version by Glen Campbell (with scrolling lyrics) and this more upbeat arrangement by Dusty Springfield.
  1. I Started a Joke by the Bee Gees – The Bee Gees are most well known for their Saturday Night Fever era disco stuff, but for a decade prior to that they recorded numerous classics, including this tear-jerker sung by Robin Gibb. The Wallflowers interpretation of the song is also excellent.
  1. Long, Long Time by Linda Ronstadt – If anyone was born to sing, it was Ronstadt. She made a career out of making covers of songs that put the originals to shame. This song is brilliantly composed, capturing the feeling of resignation over love lost or never known, and Ronstadt delivers an exquisite performance to match, supported by guitar, harpsichord, and a beautifully scored string section.
  1. Alone Again by Gilbert O’Sullivan – This one is a musical gut punch, as the singer contemplates suicide after being stood up at the altar. From there he proceeds to reflecting on the death of his parents and questioning the mercy and goodness of God. Perhaps the best presentation of the problem of evil in song.
  1. Mr. Bojangles by the Nitty Gritty Dirt Band – Written and originally recorded by Jerry Jeff Walker, the Nitty Gritty Dirt Band version is deservedly the standard, with an understated vocal and perfectly stacked instrumentation. The fact that the song is based on an actual person that Walker met in New Orleans adds to its emotive power.
  1. Mother by John Lennon – John Lennon’s father left him when he was a small boy, and his mother was tragically killed when John was 17. Such pain is not fully expressible, but this song probably comes as close as possible to doing that. The desperation in Lennon’s voice during the closing refrain is almost unbearable.
  1. Somewhere Over the Rainbow by Judy Garland – The signature song in a film whose theme is finding a way home, it captures that unique sorrow inherent to the human condition. We are all longing for home, our heavenly home “over the rainbow.” I’ve listened to this song thousands of times over half a century, and I still tear up sometimes when I hear it. For an equally melancholic rendition in a completely different arrangement, check out this version by Israel “IZ” Kamakawiwoʻole.

7 Responses to “The Saddest Songs I’ve Ever Heard”

    • Jim Spiegel


      Thanks, Lisa. I had not heard that one. What a well-written song and yes, very sad.

  1. Richard Mann


    I can offer up a couple from the same album, er, CD, entitled ‘Genius Loves Company.’ The genius being the incomparable Ray Charles who does duets with more contemporary songsters. ‘Sorry Seems To Be The Hardest Word’ with Elton John … the other is with Willie Nelson – ‘It Was A Very Good Year.’ The strings in that one set the tone for our inevitable fate.

  2. Tom


    If we go way back… 100 years or so. Look for “Where the Silvery Colorado Wends its Way” sung by Walter van Brunt on Edison records.

    Same Old Lang Syne by Dan Fogelberg.


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