Life in California, Missouri, as recalled by former resident and rising country star Kassi Ashton, sounds something like a Gillian Flynn novel. Ashton’s formative years, shaped by vicious classmates, life-threatening illness (she battled thyroid cancer in 2014), and even family secrets (her sister, still in California, didn’t come out as gay until age 31) were spent in pursuit of a single goal. “I didn’t really want to go outside and play with other kids,” she says. “I wanted to do things that would help me in my future career.”

While she plotted her escape with the doggedness of a classic Flynn heroine, her execution was more Dolly Parton than Gone Girl. “I wore six-inch heels and weird dresses to school,” she says. “I didn’t partake in that small-town mentality that everyone has to be the same, [so] people were really rude to me.” 

Ostracized by her peers, Ashton spent the bulk of her time cultivating her artistic persona—one that, then and now, involved complete creative control, from songwriting to costume design. “I always knew I wanted to be a singer; I’ve never even considered another career path. But I knew I wanted singing to be the introduction to something larger,” she says. “I learned to sew because if I come up with anything in my brain, I need to see it come to fruition.”

She eventually moved to Nashville to make her dream a reality, becoming one of CMT’s “Next Women of Country” in 2017 (other alumna include Kacey Musgraves and RaeLynn). But as in many an engrossing plot, Ashton’s attempts to leave her hometown behind only led her back to her roots. “California, Missouri,” a track off her forthcoming debut album, puts a positive spin on the past with lines like, “I was born in the wrong place in the wrong time/But sometimes the wrong way makes you the right kind.” And in her recently released video for “Violins,” she revisits a site of schoolyard trauma—leading her own high school marching band as a Hollaback Girl-style queen bee.   

The exclusive videos below—the first two installments of Ashton’s new web series, “The Look,” shot in her at-home atelier—offer a behind-the-scenes look at her soup-to-nuts creative process. More than a portrait of an artist, Ashton hopes the videos will serve as calls to action for fellow eccentrics: “I want to empower people to be 500 percent themselves,” she says. “I try to do that as much as possible, so that [others] can do so as well.”