We already know what #1 is, but today, inspired by Spinner's list of 25, I made a list of my 10. There's more, most certainly, but I've got too much work to do to add another 15.
1. “The Drugs Don’t Work” by The Verve
Holy crap, don’t even get me started or I’ll start crying right here and now. Sad, sad, sad song about someone slowly dying that gets me every time. This is, not doubt about it, the saddest song ever.
2. “I Didn’t Understand” by Elliott Smith
It’s even sadder now that he’s mysteriously dead. Well, the death isn’t a mystery. It’s how he died that’s mysterious. Still, dead depressed person formerly addicted to heroin with a pretty soul who wrote incredible lyrics = sad.
3. “They Can’t Take That Away From Me” by Fred Astaire
Not a song man, more a dance man, but this version of this song is just a sweet and poignant good-bye.
4. “If You Go Away” by Emiliana Torrini
It’s a remake of “Ne Me Quitte Pas” which is sad in and of itself, but this Icelandic sprite has changed the lyrics and made them even more weepy.
5. “Slow Tango” by Jane Siberry
CHRIST this song is sad.
6. “Fast Car” by Tracy Chapman
This is a situational thing. It reminds me of the summer after 8th grade when my family went to Hilton Head with my best friend at the time. The song was everywhere and it just calls to mind reading The Scarlet Letter and wondering a lot if Jennifer and I would still be friends after we started high school. It’s also a super sad song about dreams not coming true, incidentally.
7. Untitled song from R.E.M’s Green album
Totally a personal thing. My friend Chris was leaving for the circus (long, long story) and this was on a tape that he made me.
8. “I’ve Seen It All” by Bjork, from the movie “Dancer In The Dark”
If you haven’t seen this movie, up your dose of Thorazine and rent it. You’re going to need those numbing pills just to get through it. I’ve basically forbidden myself from watching it ever again because the last time I saw it I cried so much I used an entire box of Kleenex. I’m not kidding. An. Entire. Box. This song comes when you realize that no matter what happens, Bjork’s character's not coming out of this in a good place.
9. “Dream A Little Dream Of Me” by any number of people
Who knows why I think this song is sad? I just do.
10. “Strange Fruit” by Billie Holiday
Probably the saddest sad song about something I can’t even comprehend that happened less than a lifetime ago. All the other songs about love and loss can’t compare to the sad history this song relates.
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