Annie Clark's poise has only gotten more resolute over the course of her four albums, but her musical life began years before her 2007 debut, Marry Me. Born in Tulsa, Oklahoma, she moved to Dallas following her parents' divorce when she was three. Including step- and half-siblings, she has four brothers and four sisters, though she mostly grew up with her mom, stepdad, and two sisters. "It wasn't like 'The Brady Bunch'," she quips. Though she's loath to talk about her family with a recorder on—"That's not anybody's business"—Clark offers the following when asked about how her childhood may have affected her later accomplishments: "Pain and feeling unworthy is just as good a motivator of success as feeling like you're entitled to everything."

At the start, she wouldn't play guitar and sing unless her family was talking amongst themselves in another room, though that shyness ended quickly. She played her first show around age 15 in Dallas, performing Jimi Hendrix's "The Wind Cries Mary". Standing in the shadows near the back of the room were two musical virtuosos who flew in just for the occasion: Tuck Andress and Patti Cathcart, aka world-touring guitar-and-vocal jazz duo Tuck & Patti, aka Clark's uncle and aunt.

"Even at that early age she was able to go into an all-or-nothing performance mode," says Andress. "She was no more ridiculously outgoing than the average person, but when she was on stage she was like a fireball, even that first time."

Watch an old video of Andress playing an entire band's worth of parts just with his guitar, and his influence on his niece's fingerpicking style and posture (and swirling hair) is instantly apparent. (One YouTube commenter enthused, "He's the fucking bob ross of guitar," which probably isn't too far off.) But while Andress' sister let him know that Annie was following in his footsteps early on, he stresses that he never went out of his way to guide Clark's hand. Instead, he and Cathcart invited Clark to help them out on a Japanese tour less than a year after that first Dallas show, so she could see what the life of a musician was like up-close.

"She would be sitting in the dressing room playing guitar," remembers Andress, "and these Japanese rock stars would walk in and their eyes would open wide when they saw little Annie just tearing it up." Three years later, before heading off to Boston's prestigious Berklee College of Music, Clark road managed one of her aunt and uncle's European tours, handling everything from security, to press, to the equipment onstage.

"I was just in awe of their musicianship," says Clark of Andress and Cathcart, whose original songs and covers of hits like Cyndi Lauper's "Time After Time" could reasonably be described as easy listening. "My tastes were more rock or pop-leaning at the time, but it's unpretentious music and it moved people to tears every night. It's far too easy in this culture to dismiss someone's life's work with arrogant snark, but it's like, 'What have you ever fucking done?'"

Clark's education on the road would arguably prove to be more enlightening than her time at Berklee, where the self-taught guitarist struggled with the school's more pragmatic approach to becoming a musician. "Berklee's primary responsibility is to make you competent and employable, not to learn how to be more creative or more yourself," says Andress. "Annie found that side of it off-putting." After three years, she dropped out.

On the subject of her own startling aptitude on the guitar, Clark can be strident ("I'm an actual musician—I didn't start playing guitar yesterday") and also somewhat proudly ignorant ("I can't read music"). She bristles at the idea of being a "trained" musician. "I feel lucky that when I put my fingers down on a guitar I'm not 100 percent sure what's going to happen," she explains. "Knowledge is something to fall back on if you get stuck, but ultimately the goal is to play with abandon."

St. Vincent keyboardist Daniel Mintseris, who's studied various types of music since childhood, backs up Clark's philosophy. "More than most educated people I've met, Annie's able to use her education selectively, so she develops a language of her own," he tells me. "In some aspects she really can point out a specific step in the scale or a chord, but that doesn't come up all that often. Usually we're able to communicate musically directly—we don't need too many words."