Like a great comic book, retro-country singer Ashley Monroe’s rise to regular rotation in the house band for Jack White’s Nashville-based Third Man Records has a truly surreal origin story—one that started, innocently enough, way back in 2006, long before she released her two Vince Gill-produced solo albums for Warner Brothers, 2013’s Like a Rose and the brand-new The Blade. She and her pal Taylor Swift were sitting at their airport gate, en route to a radio show appearance, when Swift glanced at the prior flight’s disembarking passengers and gasped. “She goes, ‘Oh, my gosh! There’s Jack White! Let’s go get his autograph!’” recalls Monroe. “So we go over there, and everyone was recognizing her then, because she was really starting to blow up. He had his head down, and she was like, ‘Hi! I’m Taylor Swift!’ And he didn’t really respond, one way or the other.”
Monroe remembers thinking that was unusual at the time. But that’s not how the enigmatic Jack White rolls, she quickly discovered, as she cleared her throat and quietly introduced herself, too. White froze. “He said, ‘Ashley Monroe? The singer?’” she says. “And I thought he was making fun of my name, because it kind of sounds made up, so I was like, ‘Yeah, right—he knows who I am, but not who Taylor Swift is? Okaaayy…’” But the White Stripes/Raconteurs/Dead Weather anchor had actually heard her singing on the Grand Ole Opry while driving one night, and pulled over to the side of the road and turned off his engine to listen, he was so taken with her crystalline, mountain-spring-pure singing voice. “He even named the song I sang and said ‘I can’t believe I’m meeting you!’ And Taylor was like, ‘What is happening right now?!’ Everyone was like, ‘Why?’”
White didn’t forget her. Two years later, Monroe got an email from him, asking if she would trill on The Raconteurs’ bluegrass version of “Old Enough,” alongside C&W legend Ricky Skaggs himself; White had his own imprint—he could record whatever and with whomever he wanted. She pounced at the rare opportunity. “So that was the first time we ever hung out, and we really hit it off,” she says. “So I got to sing on the Wanda Jackson stuff he was producing and go on the road with them for a few dates. I even got to sing with Willie Nelson at Third Man for his 80th birthday party. Jack has really supported me all along, and I appreciate that, big time.”
The ultimate honor was recently bestowed on Monroe, when she was invited to record a full-length live album in a single, high-pressure take at Third Man, which was instantly pressed onto acetate, then issued on limited-edition black and blue vinyl. It features rarities, like her mournful cover of the Gram Parsons standard “Hickory Wind.” When she arrived at her benefactor’s label/studio, he was already there, checking the sound and helping with the lighting. “He really cares, and he wanted everything to be perfect,” she says. “And afterwards, he and Brendan [Benson, fellow Raconteur and one of her favorite co-writers] were waiting, right where I walked offstage, just clapping. It was like that scene from Titanic at the end, where all your friends are there, and you die. I was like, ‘My God! This is amazing! I need to do this more often!’”
But all of the vocalist’s favorite recordings were done in one take, she adds. In fact, everything about Monroe is old-school, from her collaborations (with not only White, but her honky-tonk side project The Pistol Annies, with Miranda Lambert and Angaleena Presley, and duets with Blake Shelton, like the recent CMT Award-nominated “Lonely Tonight”) to her Roger-Miller-wry phraseology on The Blade (The Elvis-meets-Jordanaires stomper “Winning Streak,” with “I got a good foundation on a bad reputation…if losing’s a game I’m on a winning streak”; the pedal-steel-loping “If the Devil Don’t Want Me” and “If the devil don’t want me/ Where the hell do I go/ If I can’t see the light in the neon glow”; and the Gothic-blues “Dixie,” via “If I ever get out of Dixie I’m gonna me buy some brand-new shoes/ I’m gonna have somebody shine ‘em up soon as I pay my dues”). It all follows classic suit mapped out on Like a Rose, courtesy of a chugging “Weed Instead of Roses” (“Give me weed instead of roses/ Bring me whiskey instead of wine/ With every puff and every shot/ You’re looking better all the time”) and the read-between-the-lines “Two Weeks Late” (“The man is gone, what a damn cliché/ And my mama says looks like I’ve gained some weight/ Landlord’s at the door, he says the rent can’t wait/ But I’m a dollar short and two weeks late”). Or, as Gill aptly put it recently, “She writes great songs and sings like a bird.”
Is Monroe an old soul? Or in touch with some bygone Carter Family era, or at least the real-deal ‘60s/’70s sincerity of female trailblazers like Dolly Parton or Loretta Lynn? She’s not certain. Ever since she was young, growing up in Knoxville, Tennessee, she somehow felt out of place, ahead of her time, she recollects. When her parents found her crying sometimes and asked what was wrong, she reported that she simply felt lonely, even though she was unsure exactly what the term signified. Like an adult, she was eerily wary of hurting others, too. “I remember my first birthday, vividly,” she says. “I didn’t like my dress, but I didn’t want to hurt my mom’s feelings, because she liked it. And that was my first birthday. So I definitely feel like I’ve probably been here many times before.”
Monroe inked her first Music Row publishing deal as a teenager, then had a debut disc called Satisfied ready to go in 2006. But the label sat on it, releasing tentative singles instead, which failed to chart, thereby keeping the full-length shelved (three years later, it would finally be issued, digitally). But by then she had blossomed into quite the popular composer, working and recording with other vintage-minded songwriters like Trent Dabbs (they put out a 2008 EP under both their names) before teaming up with Gill for Rose. Shelton chimed in on that set’s roadhouse-twangy, low-rent karaoke tale “You Ain’t Dolly (and You Ain’t Porter),” and Lambert went on to complete two rollicking albums with her as part of The Pistol Annies, 2011’s Hell on Heels and Annie Up in 2013. Shelton officiated at Monroe’s marriage to Chicago White Sox pitcher John Danks; Lambert was her maid of honor.
As easy as her team-up with White might have seemed, it hasn’t been easy carving a career in country, Monroe admits. “It’s tough,” she says. ”So tough. And I do have moments where I think, ‘Oh, I’ll just be a songwriter—I can go home and sleep in my own bed every night and be a songwriter.’ But most of that happens when I do radio shows where no one’s listening, where they just want to get drunk and they don’t care about what I’m singing. And that? I can’t explain how bad that hurts your feelings, how much it hurts that no one’s paying attention to your songs. I would rather go work at Walgreens. Me and Rodney Crowell actually wrote a song with that line in it, and I love Walgreens, I’m not bashing it. I’m just saying that I would rather work at Walgreens than be put in those positions. So I’ve definitely had my down moments.” She pauses. “But when it’s good? Like that Third Man show, when the audience listens and they care? The fire burns so deep inside of me that I realize I’ve got to keep going. I have to do this.”
Mention that Walgreens also has an insurance and retirement plan, and Monroe gushes. “I know! And I’m sure you get great discounts on all their products!” Ultimately, what keeps her happy is an emerging Nashville sisterhood—strong female writers like Lambert, Presley, Brandy Clark and Lindi Ortega, who are essentially composing circles around their more staid male counterparts. “I think we definitely all have each other’s backs,” she declares, devoutly. “All of us have known each other for a long time, and it sounds cliché to say it, but country music is a family.” For evidence, she offers another tale, wherein she wound up sharing an awards-show dressing room with one of her idols, Martina McBride.
“I mean, I grew up trying to sing her ‘Broken Wing’ on karaoke, and I could never hit that last note, I never could,” she concludes. “So I said, ‘Martina, do you still get nervous before you go out to sing?’ and she gave me some advice. And I thought, ‘How cool is that, that I can just sit here and talk to someone who’s like a legend? That I used to sing karaoke to?’ My life really is pretty amazing.”