What is the Saddest Song?

Living life to the fullest isn’t just about maximizing the happiness in it, it is also about embracing the sadness and the pain. I use the word embrace very deliberately. After all, one can’t know happiness without knowing its opposite and all that one may feel in between. If you want one side of the coin, you have to put the whole thing in your pocket. Embrace the sad, the grief, the frustration, the disappointment. Trying to ignore or suppress it only makes it worse anyway.

All of which brings me to the idea that when the sadness falls, a really sad song might be very helpful. It is reassuring to know that someone else out there is hurting, but more than that, and at the bottom of that well of tears, there is this gift: Someone has put words to your sadness, a melody to your grief, and when that gift is delivered by the perfect voice, then you have a tool by which to embrace the sadness—to face it, talk to it, understand it, and begin heading towards the next happy wave in the ups and downs of life.

I got to thinking about this while watching the PBS documentary, Country, which is really a biography of country music. No one writes or sings sad songs like the old-time country musicians, and I expect it’s because they were people who happened to sing, and not singers trying to be real people. An example from Country is the fact that Johnny Cash and Carl Perkins became immediate friends when they discovered that both had scars on their fingers from picking cotton as kids.

Most sad songs are about love that is no more, but not “Blue Bayou.” Written by Roy Orbison, who also recorded it, the most haunting version is by Linda Rondstadt. The song captures the longing for home: “I’m going back some day, come what may to Blue Bayou,” and images of that beautiful place drift by in the lyrics that follow. The sadness lies between the lines, however, for we all know that quite often “some day” never comes, and if it does, home won’t be the way we remember it.

Another “between the lines” sad song is “I’ll Be Seeing You.” The most popular version was by Bing Crosby. Released in 1944,  it’s the historical context that gives the song its sad flavor. Many families no doubt sent their boys and girls off to fight with the words, “I’ll be seeing you,” but they were said with false courage, for everyone knew that they might be parting for the last time. Another Crosby song, released the year before, contains the same theme, waiting until the last line before facing the reality: “I’ll be home for Christmas, if only in my dreams.”

Roy Orbison’s “Crying” should be on everyone’s list. “I was all right for a while, I could smile for a while . . .” And right there, after the first line everyone starts nodding. Orbison’s delivery is perfect. He just stands there, straight as can be, his voice strong and steady, but he makes you feel that at any moment, he might drop to his knees and start sobbing. But he doesn’t, and we think, Well, if he can stand there and sing that song, then I can go to work, or do whatever it is we need to do to carry on.

Many Patsy Cline songs are like that. “I Fall to Pieces,” and “Crazy” wouldn’t be so sad were it not for her strong delivery. She seems to shake her head and say between the line, “I’m doing this to myself,” and we shake our heads and say, “Yep! Me, too.” Perhaps, her saddest song is “Faded Love,” the very title of which is haunting. As Patsy sings the final line, her voice catches before the last word—“I’ll remember our faded . . . love.” Some in the studio thought this ruined the take, but producer Owen Bradley left it in much to his credit. (To add another level of poignancy, “Faded Love” was recorded in Cline’s final studio session, a month before the plane crash that took her life.)

As much as I love Patsy Cline, I’d have to say that “I’m So Lonesome I Could Cry” by Hank Williams is the saddest song I know. It’s not until the penultimate line that we learn what caused the emptiness about which Hank sings, but by that time, it doesn’t matter. We say we’re down when we’re sad, but this song shows just how far down down can get.

There’s no sense in me talking about it, anymore: Just listen. Then tell me the saddest song you know in the comments below.

About Austin Gisriel

You know the guy that records a baseball game from the West Coast in July and doesn't watch it until January just to see baseball in the winter? That's me. I'm a writer always in search of a good story, baseball or otherwise.
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8 Responses to What is the Saddest Song?

  1. Dick Snyder says:

    Another great article! I so much enjoy reading everything you write. But with that said, I’m far from sad at this point in the fall – OCTOBER 4TH – GO YANKEES! 😄⚾️😄⚾️


  2. Hunter Hollar says:

    Well said Austin, but here is old all-time sad song by Ronnie Milsap–who can sing a song about as well as anybody for my money.


  3. Jerry Lane says:

    I’m not known for being able to recite song lyrics so I’ll just posit that “I’m so Lonesome ” is surely near the top of the “Saddest” category. For all the covers of “I’m so Lonesome”, Hank Williams Sr. has no peer, IMHO. The voices of Hank and early country singers such as Jimmie Rodgers, Earnie Tubb and Bill Monroe are an acquired taste, but if an effort is made to just listen one will be vastly rewarded. They have “edge” that is not pretty or sweet. To my mind, the honest simplicity of their tone and style “makes” everything they do. That one voice accompanied by one or maybe two guitars and possibly a fiddle can do so much for a song, WOW. This genre of song does not need the full blown orchestra and choreography so typical of modern country.


  4. Don Hoover says:

    Mary and I watched most of this PBS series and I have to say it was quite educational. We knew most of the performers, however the behind the scenes of their lives and lifestyles were what really impressed us the most. Sorry to see it end last night.


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