Kara Jackson: “Dickhead Blues”

There’s an important part of the Book of Genesis that’s easy to miss. Right after God cursed womankind with painful childbirth, he threw in an even worse fate: falling for dickheads. Lord knows those men are charming at first. Then their wit turns into snark that whittles at your self-esteem. A century of weariness makes itself home in your voice, as if you’ve traversed the Western frontier with nothing but the clothes on your back and a Billie Holiday record on the Victrola.

This is the spirit of Kara Jackson’s “Dickhead Blues,” an embittered and hilarious read of asshole lovers who spout empty promises and “make a vacation out of you.” The Chicago singer-songwriter’s voice is so doleful, so tired, that listening might make a cigarette magically appear between your fingers. The instrumentation is initially spare as Jackson identifies her problem as pretentious, coffee-guzzling men—“coyotes in culottes,” she says. But the song pivots to self-affirmation—“I’m no longer amused by losers who find themselves losing me”—taking flight in the latter half as the drums build, strings swell, and xylophone twinkles. “I am pretty top-notch,” Jackson concludes, finally relinquishing care for the careless.