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“There are two kinds of people in the world: normal people who listen to a song once or twice and then move on, and weirdos who put a song on repeat for an hour, a day or sometimes even a week,” Karen Pittelman, lead singer of Americana outfit Karen & the Sorrows, quips. As a “proud weird,” she found herself obsessing over a collection of songs, enshrined in hooky melodies, haunting musicianship and universally-daunting songwriting. “I thought I’d share a few of the songs I’ve been playing again and again…and again lately,” she adds.

Pittelman’s playlist, exclusively on B-Sides & Badlands, spans fellow country outliers and pop/rock icons to one audacious purveyor of venomous, well-whipped lyricism. Enjoy one essential track from Lilly Hiatt‘s latest album, along with entries from Silversun Pickups, Gillian Welch, Radiohead and Stevie Wonder. Below, the vocalist and talented player walks us through each song, detailing personal enlightenment and exactly why she just can’t move on.

Earlier this year, Karen & the Sorrows ⎯⎯ also comprised of pedal-steel guitarist Elana Redfield and drummer Tami Johnson ⎯⎯ dropped their second roots album, The Narrow Place (out now).

“The Night David Bowie Died” by Lilly Hiatt

This song was love at first listen for me, and I’ve had it on repeat ever since she released her new album last month. I love that weary sadness in her voice. And the guitar solo that makes me think of my favorite My Bloody Valentine songs.

“Give Me the Night” by George Benson

In a Quincy-Jones-produced masterpiece like this, every layer is perfection. So, there’s always lots to obsess over when you listen to it 40 times in a row. For about a week, all I wanted to talk to anyone about was the amazing reverb on the backing vocals. It turns out this is not what most people want to talk about, in case you were wondering.

“Circadian Rhythm (Last Dance)” by Silversun Pickups

This song makes me feel like it’s 1986 and my babysitter’s daughter, with her beautiful hairsprayed-to-heaven hair, is driving me around in her Toyota Corolla with the sunroof down. I’ve been listening to this whole album, ‘Better Nature,’ on repeat.

“Women Without Whiskey” by Drive-By Truckers

This is what I love most about the Mike Cooley side of DBT. That dry wit that is both elegantly simple and unexpected. Also that variation on the guitar riff at 1:23 is probably my favorite moment.

“Supermoon” by case/lang/veirs

This song from k.d. lang, Neko Case, and Laura Veirs’ supergroup is what I’ve been listening to on repeat at 2 am when I’m lying in bed but I don’t really want to go sleep. Those echoing harmonies and eerie strings sound perfect with just the late-night light from the street lamps streaming in my bedroom window.

“Annabelle” by Gillian Welch

I love the guitar solo in this song so much, especially that delicate last bit at 2:24 that takes you back to the verse. David Rawlings is also one of my favorite harmony singers. I could listen to him and Gillian sing together all day. Well, I guess sometimes I do.

“Nobody Wants a Lonely Heart” by Arthur Russell

If you’re feeling lonesome and you want to just snuggle down into your sadness, this is the song for you. Plus, “Now as you eat, don’t think of the one you love” is one of the best opening lines ever.

“Decks Dark” by Radiohead

On the other hand, if you’re feeling lonesome, probably the worst thing you could do is listen to this Radiohead song on repeat. I can promise from experience it will only make you feel worse. Still, when that change-up hits at 3:23, it’s so, so good, I have to start it over so I can hear it happen again.

“Father Stretch My Hands Pt 1” by Kanye West

At first, I felt confused about this song’s mix of gospel, love, redemption, and the story of fucking a model who just bleached her asshole. But once I listened enough times, I started to see that Kanye is looking at how the sacred and the profane are always intertwined with each other and how this is our struggle. And then I just wanted to hear it again and again.

“I Don’t Know Why” by Stevie Wonder

This song is like a masterclass in how to use repetition. Stevie takes the simple phrase “I don’t know why I love you but I love you” and bends and breaks it every which way until your heart is in a million pieces.

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