Jill Sobule, "Karen by Night"

Rest easy, and thanks for the music.

Perhaps you’ve heard about the untimely death of singer-songwriter Jill Sobule. For decades, it’s just been one of those things in New York, where you’d hear about some far-flung project and so-and-so’s working with so-and-so, and “also Jill Sobule’s on it.” Because of course. Cartoon voice? Play writing? Solo residency? Cameo in basically anything you can think of? It was never surprising to hear her name pop up. She elevated a room with a frenetic sense of fun and an off-leash imagination, and I think people sensed that the truly outrageous idea was always a little closer when she was there.

Hey, Jill! Same guitar!

To me, Jill wrote as if she were sitting on a park bench with a friend, making up extravagantly detailed histories of ordinary passers-by. With the eye of Flannery O’Connor and the spirit of Kimmy Schmidt, she set their histories to music, but they didn’t really need music—her work could have existed as graphic novels, or a cult TV show, or maybe a collection of short stories to be read under the blankets with a flashlight.

A longtime favorite of mine is “Karen by Night,” a tale about her normie boss at a shoe store who transforms into a badass superhero after hours.

Karen by night
The leather comes out under the moonlight
Takes off her Chanel and hops on her bike
Looking like young Marlon Brando
Karen by night

Beyond being a fun song, it reminds me that normalcy is a fraud, a ruse, a patsy for our secret lives that grow more empathetic and human the more they explode into implausibility. If that’s what’s in Karen, can you imagine what’s in the guy sitting across from you in the subway? Or in anybody? Or in you? She still helps me ask those questions, in my music, and in my life.

Rest easy, Jill. Perhaps we’ll open for Warren Zevon again, soon. But you do the talking this time, I’m not sure he likes me.

Enjoy:

Music, Lyrics, and Life, available in print and audiobook.

Signed copies are available at 25% off on Bandcamp with the promo code: substack2025

…or, if this is all too much capitalism, you could just buy me a coffee.