Bailey Bryan
Photo: Nikko LaMere / Courtesy of Shore Fire Media

Bailey Bryan Brings Her “Sensitive Bad Bitch Music” to Bonnaroo and Beyond

Bailey Bryan shifted gears after moving to Nashville and is making the most of a Fresh Start ahead of her first major tour as a pop-R&B headliner.

Fresh Start
Bailey Bryan
300 Entertainment
7 May 2021

While emerging pop-R&B singer-songwriter Bailey Bryan has always shown a passion and unbridled enthusiasm for performing, the genuine excitement she expresses in advance of a 2021 tour exceeds the normal eagerness of most traveling musicians. Especially after the abnormal circumstances caused by last year’s pandemic. 

For one thing, the Nashville-based 23-year-old artist, coming off the 7 May release of the aptly titled project Fresh Start, will make her major headlining debut with 17 dates over the next two months, starting at the Moroccan Lounge in Los Angeles on 21 September. Even better, she’ll get to try out her act with a debut performance at the Bonnaroo Music and Arts Festival on Friday afternoon (3 September). 

“Oh my God! Dude, I’ve been going every summer to Bonnaroo for four [consecutive] years [until it was canceled in 2020],” Bryan exclaims, practically screaming over the phone on 5 August after recently moving into a Nashville rental upgrade. “It’s my favorite festival. It’s really the only music festival I’ve ever attended.” 

Watching some of the best musical acts in the world from the famed festival previously held in June in Manchester, Tennessee, after moving to Nashville in 2016, Bryan would camp out on those hot summer nights in a trailer provided by her music management company with one thought in mind. “Every year, I’d be like, ‘I’m gonna play this festival pretty soon, guys,’” she recalls. “Then summer would roll around and I’d be like, ‘OK, next summer!’ Now it’s finally happening, so it makes me so excited. I’m playing the ‘Who Stage.’ It’s fitting. It’s like, ‘Who?’ And I’m just like, ‘I’m so excited!’” 

Told it’s been billed elsewhere as the “Who’s Next Stage” only adds to her sheer joy. “Ohhh! I love that!” Bryan adds. “I did not think of it that way. (laughs) I love that. I thought of it like, ‘Who the heck is this?’ It fits either way.” 

Repeatedly acknowledging (perhaps half-kiddingly) that she likes to “keep the expectations low” whether it involves reaction to her album, videos, or tour, Bryan possesses a sunny-bright optimism and sweet, almost innocent effervescence. Both glowing qualities complement her charismatic personality and movie star magnetism. Yet nothing seems fake about her feelings regarding life in general and Bonnaroo in particular. 

“The fact that I get to show up is a dream come true in itself,” she continues. “I have so much fun at Bonnaroo. The best thing about Bonnaroo is it’s a really, really positive environment. I feel like everybody is always very happy and supportive, which is really impressive, considering the fact that it’s always so, like, a thousand degrees there and dusty. 

“I don’t know how everyone’s in a good mood, but it’s just the environment. I think it’s a perfect way to kind of kick off this season of getting back into live shows for me because I think the audience will be welcoming. Even if they’re all like, ‘Who the heck is this?’ they’ll probably be nice to me.”

Who could behave any other way? Bryan’s refreshing outlook and self-deprecating humor are clear signs that are prevalent throughout our hour-long conversation, making it hard to believe only days earlier she was feeling under the weather with “just a bad cold” after previously getting vaccinated, then passing a COVID test. “I did one of those IVs with all the vitamins and stuff, and I think it really helped. But I hate needles so much,” Bryan admits. “This dude, this really sweet person from this company, came to my house and was really great about it. … I was fighting back tears when he was getting ready to put the IV in. … Once it’s in, I’m fine. But like the poking part …” 

No wonder Bryan’s fans (nearing 200,000 followers on TikTok) can identify with a rising pop star who grew up in Washington state as a three-sport athlete but “never liked sports that much” and disliked math class even more before beginning her career as a country artist. At age 16, she underwent surgery for scoliosis (curvature of the spine) and experienced a “hard physical recovery” but found inspiration to write the song “Scars”. By displaying such courage in facing a life-altering moment, considering a music-making shift was minimal by comparison.

Brave enough to exit country music and eventually create what she calls “Sensitive Bad Bitch Music” coincided with searching for happiness, confidence, and independence along the way. In this charming interview with PopMatters, Bryan details how writing songs first brought to her Nashville, what to expect during the upcoming concert tour and why such a “relationship person” at heart is getting a Fresh Start. (And don’t miss the PopMatters PopQuiz this really good sport takes to conclude the article.)

A Taste Worth Savoring

Born on 31 January 1998 to Jay and Heidi Bryan and raised in Sequim (pronounced SKWIM), Washington, Bailey MyOwn Bryan — the middle name inherited from her mother — soon realized there weren’t “a ton of music opportunities” available in a place with only four stoplights. While growing up In this “really little, beautiful town a few hours outside Seattle,” the self-professed “introvert at heart” sang in church and school choirs. 

“As soon as I knew it was kind of like an option like it was a thing people did with their lives, I wanted to be a famous singer,” states Bryan. “Then I learned, OK, you can write your music. You can make a career out of it. And I said, ‘I want to be a singer-songwriter.’

“I was that kid when my parents would have their friends over, I would gather everybody in the living room and make them watch a dance that I made up. It’s always been the thing that I love to do the most — perform and create and make people look at what I’m performing and creating.” 

After teaching herself to play three chords at age 12 only to become “a painfully mediocre guitar player,” Bryan decided, “When I was old enough to where I was asking my parents to buy me things, they’re like, ‘Well, you’re 15. You should just get a job.’ I took my guitar and I played music on the sidewalk [busking] for tips outside my favorite taco place.” 

Bryan speaks lovingly of Jose’s Famous Salsa, saying, “I haven’t been back in a minute, but their salsa is so good. Jose would give me a sombrero to wear sometimes outside of the store. I didn’t really like it but, you know, if he’s letting me loiter outside of his business, I’ll wear it.” (laughs) 

Her “super-tall” father, a former basketball player at Eastern Washington University who grooved to rock CDs at the house, and “real cute” mother, whose preference was ’90s R&B like Brandy, TLC and Destiny’s Child, never had musical ambitions for themselves and owned the Anytime Fitness club in Sequim. 

“I don’t know how they got two musical kids,” Bryan confesses, reporting that her 19-year-old brother Cooper will soon move into big sister’s three-bedroom home, where they’ll turn that extra room into a studio. Yet when her parents knew their daughter had an aversion to basketball (“I just didn’t really like practicing”) and schoolwork (“I’m not an idiot but do I wanna read things about math in my free time?”), they helped her “find whatever opportunities I could” in music. 

While all those influences were streaming into her consciousness, Bryan states, “Taylor Swift was kind of a reason I had this dream of moving to Nashville from a pretty young age,” after listening to her debut album. 

Besides vintage Swift, though, Bryan kept enjoying and studying a wide range of genres and artists from Chance the Rapper and Post Malone to JoJo and Kehlani, conceding, “I don’t think I could ever identify as a country girl.” 

Yet that was her ticket to the Music City.  

Bailey Bryan
Photo: Acacia Evans / Courtesy of Shore Fire Media

Country Comfort for a Minute

At 15, Bryan began visiting Nashville regularly to write songs, and signed her first deal with Kompass Music Publishing, “a company that kind of took a chance on me” that was run by family friend Becki Devries and Dennis Matkosky. 

Called “country music’s newest leading lady” by People and nominated by Hillary Scott, co-lead singer of the group now known as Lady A, for the fan-voted Grammy Artist of Tomorrow award in 2017, Bryan has fun with the latter distinction. “I still don’t really know what it means. But it was definitely a cool thing for me,” she shares, shouting in mock disgust about finishing second to Drake White (“How dare he!”). That simply meant her day in the sun was still to come.

Unlike others who felt betrayed by the country music industry at some point in their careers, Bryan doesn’t seem bitter — maybe just a little misunderstood — in explaining why she took her career in another direction. Guided by Red Light Management’s Callie Cunningham, who’s “definitely helped raise me a little,” Bryan calls her “my closest co-conspirator” since becoming a client at age 17.

“Honestly, I think I was really going through a major Taylor Swift phase when I started writing professionally and coming to Nashville,” Bryan reasons. “When you’re figuring out who you are and what you want your sound to be as an artist, you do it by emulating what you like and what you’re listening to at the moment. … So it was country, you know, for a minute. And I’m really grateful that I got my start as a writer in country music just because the focus is so much on the lyrics and the story and — even if I’m in pop or R&B, hip-hop, whatever — I could never be lazy with my writing. I really want it to say something. And I credit Nashville and a country music background for that a lot.”  

Also signed at 17 to New York-based 300 Entertainment, known primarily for hip-hop, pop and R&B, while Warner Music Nashville helped direct her country career, Bryan began evolving as an artist through daily cowrites and studio experiences for EPs like 2017’s So Far (buoyed by debut single “Own It”) and 2019’s Perspective

She asked herself, “What does my voice even sound like? What kind of production do I like?” Her inner voice replied, “A double shot of pop and R&B.”

Bryan’s parents knew it was all happening, though. After staying in Nashville with their daughter for less than a year and watching her get the record deal, turn 18 and graduate from high school by taking online courses, Bryan recollects, “They were like, ‘All right, you’re good! ‘Cause we miss Washington.’ They kind of helped me get my footing here and I think I got a really cool team around me way quicker than anybody expected when I moved here.” 

Jay and Heidi sold their fitness business, moved to a cabin in the Bavarian-style village of Leavenworth, Washington, in the Cascade Mountains, while Bryan’s little brother — “the cooler, younger boy version of me,” she modestly claims — continues exploring music and living “in a tiny house in their backyard making beats” before joining his sister.

Although her parents may have made a stunningly shrewd lifestyle move, Bryan’s genre shapeshifting shouldn’t be viewed as either surprising or surreptitious. 

“I didn’t actually go to my team and be like [whispering], “Hey, guys, I know we’re doing this country thing, but I want to switch.’ It was actually them coming to me,” declares Bryan, who was totally receptive to the idea after already considering a change.

“The biggest roadblock for me when I started in country was people kind of not really believing it. Which I get. They were just like, ‘Why is she in country? She seems to like other kinds of music and she wears sneakers and doesn’t know any Garth Brooks songs. What is she doing here?’ And I’ve just been like, ‘I don’t know. I’m making the music that I’m making. I don’t care what you call it.’” 

Stating “we don’t care what genre you are,” 300 Entertainment offered firm backing, according to Bryan, and she was supported by Warner Nashville (the label was “super-cool” about her position). Maturing before their eyes while leaving that teenage country girl behind, there was a brainstorming innovator at work who felt comfortable realizing, “It was a really natural kind of painless process. If we’re being honest, I think that’s just because it was the most authentic thing for me to do.”  

All grown up, Bailey Bryan was fully prepared to make a Fresh Start.