When Bailey Callahan arrived in Nashville as a tall, blonde 14-year-old with ambitions to be the next Taylor Swift, she was told that wasn’t cool. If she was going to make it Music City, she needed to be the next Bailey Callahan. But the memo about individuality came a little too late. By the time she released her 2014 EP, Tear It Up, she already hated it.
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Back to the drawing board while back home in Winter Park, Florida, the aspiring artist honed her voice, who she was, and what she wanted to say with her music. This self-discovery coalesced in her 2017 self-titled EP.
Though a pivotal point in her artistic direction, the industry folks told her to come back next year when she was 18—when they could do more for her as an “adult.” Her eighteenth birthday came and went, and her perceived “start date” got pushed again to 21, when she could “drink at the Broadway bars.”
“Unbeknownst to them, I’ve been drinking this whole time,” the now 21-year-old artist tells American Songwriter over the phone, laughing. As exhibited in “Sweet Tea” (2019) and “Roll” (2020), she took her frustrations with they age discrimination and went rogue.
“I think that’s the point I got really hardcore,” Callahan recalls. “So I turned into almost like the girl verison of Eric Church, with that image of someone that wouldn’t take that shit. And I ended up really liking it. If you can be portrayed as a badass for a living, why wouldn’t you?”
Unfortunately, this energized shift aligned with the onset of the pandemic last March. For the first time since she was 11 years old, the artist was sitting still. She had her first July Fourth holiday off from work, her boyfriend moved in, which she described as a “learning experience,” and for the first time Callahan—who completed virtual high school and forwent college for her career—began to rebel.
“Oh man, did I learn a lot about myself,” she shares. “I learned about who I was as a woman, songwriter, and artist all at the same time. To cope with the difficulty I was experiencing I wrote. And I wrote the kind of songs that spilled right out of me.”
She continues, “I cussed for the first time in one of them. After so many years working at this, it finally didn’t feel forced. These songs portrayed who I am naturally. Not having to put on some persona, I was genuinely being me.”
In the past, she would stop a song in its tracks if she didn’t love it right off the bat. This time around, she kept digging. Callahan cites her song, “Flip the Coin”—the one she is most proud of from her forthcoming album, The A & B Sides—as an example of this persistence. She says, “I probably called my mom like 11 times while writing because I was frustrated that I couldn’t get the hook.”
Can’t flip a coin without some change, she sings brazenly over the phone with startling vocal talent. She continues, “I was so excited when I finally got that one, and called back to sing it for her. I also showed it to my brother, Aidan, who suggested another line edit so he’s credited on the song as a writer.”
In the process of writing this album, a duality emerged from her songs that became glaring. Songs like “Flip the Coin” and her opening track and single, “Bitter,” reflect the more rock edge her fans are familiar with. But, in the stillness of COVID-19 lockdown, Callahan subconsciously reached back into her gentler girl-country roots. Songs like “Dawning” and the album closer, “Together Again,” are reminiscent of the singer-songwriter spirit that chased Taylor Swift to Nashville all those years ago.
On June 4, Callahan shares her first full-length album, The A & B Sides. Like a vintage vinyl record, she splits her song stories into dueling categories. The artist penned four of the songs solo and partnered with Jared Anderson, Johnny Clawson, Davis Branch, and Kyle Sturrock on the remaining five.
“City Lights,” her final track off the record ahead of release, is one of those Callahan says she couldn’t have written with anyone else. “The raunchy version,” she discloses, “is that I was single, and sleeping around for the first time, and I didn’t like it. I felt weird. I was drinking wine alone on my couch one night watching TV, and it came to me. So I picked up my guitar and began to play.”
As one of her most intimate songs yet, Callahan feels it wouldn’t be fair to herself or her fans to not include “City Lights” and similarly-styled tracks on the album.
In the studio with her longtime producer, Robbie Artress (Priscilla Block), Callahan brought her dyadic vision for the album to life.
“I thought I knew what to say before writing this, and as I started writing I found out what I really needed to say,” says Callahan. “And I always knew there were two sides to myself, maybe I was just not willing to admit it. But this is me accepting, there is a huge part of me that others don’t get to see.”
Listen to Bailey Callahan’s debut LP The A & B Sides below. A limited-edition vinyl album is available, here.
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