Michelle Billingsley Cuts Through The Chase On Biting & Enigmatic “When Will You Learn”

Michelle Billingsley is not your typical folk singer. For starters, in her own words, “Folk music does not talk about f*cking.” But she does. Billingsley sings about a whole lot of subjects considered taboo for polite women. Though you might not catch it on first listen—she wraps her charmingly cutting lyrics in boisterous acoustic strumming, her dryly dark sense of humor and a (whip)smart-assed vocal delivery. It all sounds a bit like Emmylou Harris went through the looking glass.

Billingsley’s new debut album for Western Myth Records, Not the Marrying Kind (out 6/12 on Western Myth Records)—produced by her friend, multi-instrumentalist Matt Brown—is an Americana gem. Out of the gates, Brown made the sage choice of putting legendary producer/engineer Brian Deck (Modest Mouse, Josh Ritter, Iron & Wine) behind the boards—and the drum kit—for the sessions. The resulting record is genuine, irreverent, unique and fearless. Its spare, moody vibe draws you in close with your guard down, and once you pause long enough to get your head around the songs, the depth of Billingsley’s talent comes sharply into focus. It’s a deceptively heavy record, yet somehow it’s still undeniably fun—fantastic whimsy mixed with black comedy and brisk little melodies that make the journey all the more powerful, human and affecting.

As fully formed of an artistic statement as the record is, it’s hard to believe Billingsley had exclusively been performing other people’s music until she started writing Not the Marrying Kind. Her work was the culmination of much romantic and artistic frustration. “I remember walking down the street because the CTA rush hour buses come every 25 minutes,” the Chicago-based artist says. “I was thinking about how hard it was to find something to sing in my range, and then this bubble burst in my head and I thought, ‘I can write songs and say whatever I want.’”

Many of the songs from this period deal with the dysfunctional relationship Billingsley was caught up in for more than a decade. “I think, ‘I’m great, I’ve moved on,'” she says. “Then I’ll flash wide awake at 3 a.m.—‘How could I have been so stupid for so long?!’ But then I take a breath and I remember, ‘That’s how I got where I am now, and now is good.'”

Glide is proud to premiere “When Will You Learn” (below) a dusty ditty that carries a spaghetti western aroma mixed with the knock em dead bravado of Nancy Sinatra and blunt story-telling knack of Neko Case.

“When I wrote “When Will You Learn,” I was listening to a ton of Kris Kristofferson, and I can see how much he influenced this song,” says Billingsley. “I hadn’t really heard him before so I totally binged on him, album after album straight through, and his storylines kept getting mixed up in my head. “When Will You Learn” feels like it was set in some fever dream where the characters from “Silver Tongued Devil” and “Chase the Feeling” are sharing a drink. Hell, the line “she was younger than her sister, younger than alright” was almost too obvious a tip of the hat, but no one’s pointed it out to me yet. So I’m keeping it.”