Listening to Nashville-based singer-songwriter Jillian Jacqueline gush about her recent late night debut on Late Night With Seth Meyers — one of the “most surreal moments” of her life — it’s surprising to find the veteran performer so starstruck. After all, she was hand-picked to tour with Kenny Rogers at nine years old, will soon hit the road with Thomas Rhett and Brett Eldredge and has written and recorded alongside the Eagles’ Vince Gill and Richard Marx.
But Jacqueline is excited, and for good reason. After inking a deal with Big Loud Records — making her the label’s first female signee — in October 2016, the 29-year-old went on to release her debut EP Side A in September, a startlingly honest collection of break-up ballads inspired by the fallout of her five-year relationship. Standout “Reasons,” a bittersweet melody about falling out of love, is currently climbing the Country Airplay charts, where it sits at No. 55 for the week of March 24.
“I think the complexity of being a human is my theme,” Jacqueline offers with a wry laugh, but the statement is sincere. “Self-reflection is really important to me — I want the songs I write to feel like journal entries.” She opens up easily, delving into the times she’d “eat lunch in the bathroom” in high school before finding her footing in college and why releasing her EP felt like “jumping off a cliff naked.”
Jacqueline’s earliest memories of music take place in the backseat of her mother’s car in Chester Springs, Pa., where she’d sing along to Elvis and Patsy Cline on the way to kindergarten. “I was obsessed with the radio, and it built this tunnel in my head of, ‘That’s what I wanna do,’” she says. “I never questioned it.” By age seven, she began performing at local open mic nights, using a photo she jokes her mom “found in a drawer” as her headshot. With her three sisters, she formed The Little Women Band, named for the Louisa May Alcott book.
Then, around her ninth birthday, an audition listing to join a children’s choir on Kenny Rogers’ holiday-themed Broadway production Christmas from the Heart caught her eye. Jacqueline admits she had little notion of the country legend’s fame — nor, as she would soon find, how much earning the role would boost her career — when she and her mother drove three hours to Manhattan after school to make it to tryouts.
“It was stage kid central,” Jacqueline remembers. She arrived late, and in her mind, bombed the audition: “I couldn’t dance and I had two different pairs of socks on,” she recalls. But her rendition of “Tomorrow” from Annie stunned Rogers, and she scored the part. Shortly after, Jacqueline and her family moved to New York City, and her three-month Broadway stint turned into a five-year tour. “It changed my life, and Kenny became a huge mentor,” Jacqueline says. “It was a step into another world of, ‘I don’t have to be a regular kid. My life can look a lot different.’”
After studying marketing at the University of Philadelphia on the strength of a recommendation letter from Rogers himself, Jacqueline was eager to make music her priority once again. Moving to Nashville after graduation in 2010, she waitressed and took up freelance photography to pay her rent while playing local gigs, eventually catching the attention of Downtown Publishing’s Steve Markland, who signed her in 2014. A record deal with Big Loud followed two years later, as Jacqueline joined a roster of four male artists including Jake Owen. “I realized it wasn’t that they needed a girl to fill their roster — they loved what I did regardless,” she recalls. “On the same coin, they wanted me to be the first female that represents their company, and I think they value what I have to say as a female country artist. By the time I signed, it was just a question of, ‘When can we get the music out?’”
Jacqueline says she had around 15 songs ready to go by the time she signed to Big Loud, most written in the throes of a breakup with her long-term boyfriend. In fact, she was still living with her ex when she wrote the heartbreaking “Reasons,” now passing 13 million streams on Spotify, and pitched the concept to co-writer Tofer Brown as a fictional story before realizing that it paralleled her life. Soon after, she moved out: “I was just sort of unfolding the truth, and once I put [it] into the song, I couldn’t take it back…I was like, ‘Oh shit, this is true.’”
That same transparency is key throughout the EP, with Jacqueline touching on self-acceptance (“God Bless This Mess”), how sometimes “love and misery look the same” (“Sugar and Salt”) and the ripping-off-the-band-aid moment that comes with every split (“Hate Me”).
By late 2018, she hopes to release her yet-untitled debut LP, which will be “the most bare-bones of me that I can give you.” And already next month, she’ll kick off a string of spring tour dates opening for Rhett and Eldredge. But in Jacqueline’s eyes, the most meaningful milestone she has yet to experience will take her back to the place she first started: in the car, but this time in the front seat. “I’m hoping that pretty soon I’ll be driving down the road, and all of a sudden will hear my name on the radio,” she says now with wonder. “I will definitely have to stop the car and have a moment.”