More Web Laziness, Negligence and Incompetence: “The Saddest Songs In History”

I know, I know: these slideshows are clickbait. That’s no excuse for presenting what is supposed to be a definitive list when you haven’t done any research, talked to anyone with more perspective than you, or bothered to even think hard about what you are doing.

A web hack named James Cannon purported to have a slideshow of the 40 “saddest” songs “in history,” —someone may have even paid him for it—but as is usually the case with such stunts, “history” meant the obscenely narrow band of this guy’s experience, Because he didn’t know what he was talking about, he had to resort to filler, including songs that aren’t sad by any standard, like “It’s a Wonderful World,” while somehow missing classic songs that are world famous as heart-breakers. like, for heaven’s sake, “Danny Boy,” written by English songwriter Frederic Weatherly in 1913, and set to the traditional Irish melody of “Londonderry Air.” The song is still played at funerals, which would be a big hint, if Cannon performed a modicum of due diligence before making readers culturally and musically ignorant.

My objective isn’t to argue about all 40 songs; he’s as welcome to his list as I am to mine. But if your category is “history,” you can’t limit the field to recent pop music, which is, with a few (and seemingly arbitrary) exceptions what he does. You can’t make the list he purports to have made and completely stiff country western music, which is famously sad. This Hank Williams classic isn’t on the list of 40, for example:

And Hank wrote and sang many other sad songs; he had a sad life. The list also ignores Broadway, which is just nuts, frankly. This ballad from a forgotten musical called “All American” has been covered over a hundred times, and that’s because it is a killer. Bobby Darin did this painful version shortly after he had divorced the love of his life, Sandra Dee:

There are lots of competitors for saddest Broadway song, but Cannon apparently didn’t bother to listen for any of them. Also beyond his experience or work ethic is Tin Pan Alley, which has given us some of the saddest songs imaginable. Judy Garland specialized in them, with songs like,


The list includes songs that are wistful, reflective and yearning, so how did “Over the Rainbow” miss the cut? Because the writer is lazy and wasn’t paying attention, that’s how. Did he consider the saddest Christmas song of all time, “Have Yourself A Merry Little Christmas”? Of course not.

I subjected myself to clicking through the entire 40 slides, looking specifically for three epic songs of loss and yearning to determine if the list had any integrity at all. No list that was assembled with any care by someone with a rudimentary knowledge of music history could fail to include them; right up to Number 1, “Nothing Compares 2 U” by Sinéad O’Connor (Meh), I assumed one would show up, validating the exercise a little bit. Nope.

Here are the three:

If you don’t like Billie–she is an acquired taste to be sure— there are dozens of other recordings of this iconic World War 2 iconic lament.


This song’s back story (I have never been able to verify it) makes it sadder still. Supposedly the lyrics were adapted from a letter left by a man whose wife had been sitting by his bedside for days as he was dying. She woke up to find that he had passed when she fell asleep. Ugh. Gets me every time.

But the clear winner is this immortal Gary White song, which Linda Ronstadt has said, and I agree, will probably stand as the song she’s most associated with. Few singers have the guts to cover it, because you just can’t rip hearts out any better.

24 thoughts on “More Web Laziness, Negligence and Incompetence: “The Saddest Songs In History”

  1. “Against All Odds” by Phil Collins makes me cry every time.

    “Have Yourself A Merry Little Christmas” is sad so long as its Judy’s version and not the one that Frank sang after having it pepped up. “Hang a shining star upon the highest bough” instead of “Until then, we’ll just have to muddle through somehow” makes a big difference.

    He probably never heard either version, though.

  2. Speaking of Linda Ronstadt, how about “Guess It Doesn’t Matter Anymore?” About as sad as they come, and nobody could do it as well. Here’s a live version:

      • Haven’t heard that one, I’ll have to look it up.

        Linda has a ton of sad songs. Hell, she may be the modern queen of the genre. “Tracks of my Tears,” “The Moon’s a Harsh Mistress,” there’s just one after another.

          • I haven’t looked at the list and won’t. Is “I Can’t Make You Love Me,” covered by Bonnie Raitt, on the list. The quintessential unrequited love song. “Tell Laura I love Her?” The epitome of ’50s morbidity. I find “I’ll be Home for Christmas” almost unbearable. Or how about Richie Havens’ rendition of “Morning, Morning.” The most brutal portrayal of clinical depression I’ve ever seen expressed in art.

      • I actually prefer Buddy Holly’s version, but my tastes tend to run to a little quicker, more upbeat versions of more than one song.

  3. The list, if you haven’t gone through it, really is pathetic. “God Only Knows” by the Beachboys? I’m not sure any Beatles song belongs on the list, but if one does, it isn’t “Yesterday.” “For No One,” “She’s Leaving Home” and surely “While My Guitar Softly Weeps” deserve mention ahead of that one.

  4. This guy didn’t even bother to add “Gone Away” by The Offspring. Its acoustic cover version is heartrending. It doesn’t hit as hard as Eric Clapton’s Tears in Heaven, but part of that may be from knowing where Clapton was when he wrote that one.

  5. Since I heard it long ago, Stevie Nicks “Beauty and the Beast” (No, not the movie one) was always the saddest song I’ve heard.

  6. Even Elvis Presley called “I’m So Lonesome I Could Cry” the “saddest song I’ve ever heard.” Of course, country music is so replete with really sad songs that choosing a “saddest” is largely a matter of personal preference. For me, Vern Gosdin’s “Chiseled in Stone” and George Jones’ “He Stopped Loving Her Today” are the saddest. Losing all four grandparents and a few aunts and uncles to the Grim Reaper before I was out of my teens makes me a sucker for songs about loss and death of loved ones.
    Concerning Linda Ronstadt, I always though her cover of Roy Orbison’s “Blue Bayou” was the saddest of her repertoire.

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