Sir Elton John said it best (er, or at all): Sad songs say so much.
I got a real kick out of last week’s “Lady Songs” so I decided to start another theme week. But instead of pining / humorous / pitiful songs featuring a lady’s name in the title, I figured I’d take a walk down Depressing Lane and (starting tomorrow!) come up with some of the best, saddest, songs that I know.
It might sound like a pretty morose theme for an entire week, but let me explain: just because a song is sad doesn’t mean it’s bad. It doesn’t even have to be about a sad topic; sometimes the melody or the key or the what-have-you just implies a sort of musical melancholy that hits me in just the right spot. Sometimes you just need to hear a sad song to cheer you up. Twisted? Maybe.
So what songs get you each time?
the sloppy copy 
I don’t think it’s even really about anything sad, but when I heard Hoobastank’s “The Reason,” I pictured a guy who lost someone he had treated poorly and no longer has the chance to make things right (cuz they died or something morbid like that) and sings about it in the song. And so that song makes me sad every time I hear it. I dunno why I interpreted it that way. Something about the way he sings it.
For years, James Taylor’s “Fire and Rain” made me cry every time I heard it. Actually, about half of James Taylor’s songs have made me cry at one point or another. He’s got a lot of sadness in his voice. Sad songs, like sad movies, are among my faves, so here’s a short list, off the top of my head: “Tears in Heaven,” Eric Clapton (an obvious choice, but no less poignant for being so), “Painters” by Jewel (a sentimental choice from my angsty high school days), and my current favorite sad song “I Know It’s Over” by the late, great Jeff Buckley. Buckley having died way, WAY too young makes it even sadder.
Michelle, I agree with you on “The Reason.” The way he just belts it out is just sad.
Katie, thanks for reminding me of some of these. Now I’m thinking about Jeff Buckley and getting sad
“Ashokan Farewell”