I went downstairs to eat lunch and realized that I couldn’t leave Pete Seeger’s “Where Have All The Flowers Gone?” out of the discussion started in the last post.
It may not be one of the 40 saddest songs of all time, but I know this: Marlene Dietrich’s performance of the anti-war ballad was the most emotional performance of any song I have ever witnessed in my life. She used “Where Have All The Flowers Gone?” as the encore in her concerts, and the combination of her unique voice, amazing face, and what we know of her activities during the war, made the whole package overwhelming.
Here it is, essentially the same performance I saw live, almost 20 years later.
Ethics Alarms 
I didn’t have a chance to listen to the whole song, but the first verses were something. Then I looked up the lyrics and the final verse hit me like a bag of bricks. To sing that song without her voice breaking must be something.
I’ll admit that I didn’t look at the list, but I did get a sense of what made it from the OP comments section. I wouldn’t disagree with any of the addenda above or in the previous post comments.
However, how could anyone leave off Cole Porter’s “Ev’ry Time We Say Goodbye”? I’ve always thought it to have been maybe the saddest love song ever written. Can’t really beat Ella’s version, but then there’s the one by Ray Charles, too. I get moist just thinking about it.
Not to be left out are a few classical pieces that just tear your heart out: Barber’s Adagio, Albinoni’s Adagio, and I’d even include the 2nd movement of Beethoven’s 7th Symphony. These all work for me, but I didn’t know if the original clickbait specified “pop” tunes.
MB
I started down the opera and operetta road, but this guy never heard of Rodgers, Berlin, Porter, Gershwin, Sondheim, Loesser…that was obviously way beyond him.
Typo fixed…
I clicked through the list. I agree the guy has tunnel vision. Here are some on my list: “Drive” by The Cars 1984. “Memphis Tennessee” – the Johnny Rivers cover. I choke up every time I hear it. And, can a protest song be also sad? “Strange Fruit” by Billie Holiday.
Yes.
“Memphis Tennessee” is an interesting choice. Not all sad songs have to be downbeat.