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20. Smokey Robinson, "The Tracks of My Tears"
Like "Crying in the Rain," this is another song about maintaining your pride by not crying in front of the person who dumped you. Though I would recommend you be honest about your feelings with the people you care about, even if they've hurt you.
19. The Beach Boys, "The Old Master Painter"
Sometimes something so simple can be so effective. Here, it's changing the lyrics of "You Are My Sunshine" to the past tense, combining with Brian Wilson's new music to make something hauntingly sad.
18. Magnetic Fields, "Meaningless"
This delivers the perfect dose of cynicism and despair in Stephin Merritt's typically droll and witty lyrics. "Meaningless, like when two fireflies fluoresce, just like everything I guess, less less yes, it was totally meaningless." Amen.
17. Alabama Shakes, "Heartbreaker"
What I like so much about this song, besides Brittany Howard's howlingly wounded delivery, is the implication of the lyrics. "How was I supposed to know you was a heartbreaker?," she sings, as though being a heartbreaker is who this guy is, and breaking a heart not just something he once did.
16. Fiona Apple, "Oh Well"
I imagined some of you giving me shit for putting Fiona Apple on here, but you know what? Fuck it—she's awesome! Her draggy, jerky piano part here creates the perfect landscape here for "oh, Fiona" lyrics like "A voice once stentorian is now again meek and muffled!"