Maia Sharp
Photo: Black Oak Artists

Maia Sharp on Testing Her Own Truths

For singer-songwriter Maia Sharp, every song is both a mirror and a map, a way of testing her truths against the larger, shifting world.

Tomboy
Maia Sharp
Crooked Crown
12 September 2025

On the surface, Maia Sharp’s songs sound effortless—phrases that float with conversational ease, melodies that feel inevitable once you’ve heard them. Ease, however, is an illusion; the heart of her craft is wrestling with uncertainty. For Sharp, every song is both a mirror and a map, a way of testing her own truths against the larger, shifting world.

“I’ve always tried to find that line right at the intersection of confidence and humility,” she tells PopMatters. “And it hasn’t always been easy. But I’ve pushed myself through the songwriting. It’s how I find out who I am.”

That pursuit—part excavation, part surrender—has defined her decades-long career. Across ten albums and countless collaborations, Sharp has favored questions over answers, inviting listeners not to follow her lead but to walk beside her in the search. “I know I’ve been careful over the years to not sound like I think I have the answers,” she added. “But, like, hey, let’s all look for the answer, period. That just feels more relatable, more universal.”

The Storm Before the Calm

When Maia Sharp left California after decades—trading the dry light of Los Angeles for Nashville’s humid thrum—she stepped into a kind of free fall. She had dissolved a 21–year marriage, left behind a community she once thought permanent, and entered a city that hums with ambition and competition. It could have swallowed her. Instead, it became a proving ground.

Her 2021 record, Mercy Rising, sounds like someone writing from the center of the cyclone. “So much of that album was written from the eye of the storm,” she remembers. “The upheaval was self-imposed, but it was still, what have I done? Everything was uncertain.” The songs carry that vertigo: equal parts exhilaration and ache, the sound of someone remapping her own life.

By 2023’s Reckless Thoughts, the ground had steadied—though not without its scars. She survived an actual tornado, weathered a brutal bout of COVID that left her winded for weeks, and found a rhythm in her new city. Her songs shifted in tone: less panicked, more contemplative, like journal entries written in the pause after a storm has passed. “That record felt calmer, maybe a little wiser,” Sharp says. “But still absolutely en route.”

The single “Old Dreams” captures that pivot, its refrain a revelation: what I want is ever-changing, and that’s okay. “There’s no real arrival,” Sharp says. “And I love that.”

Tomboy: The Next Chapter

Maia Sharp’s newest release, Tomboy, is the most playful and raw of the bunch. It brims with percussive energy, an insistence on rhythm and motion, even as its lyrics look backward. “I wanted to keep it percussive, not slick or perfect,” Sharp says. “The fun I had showed up in this album, and I want to keep bringing that out.”

The title track rewinds to childhood, where Sharp, at five years old, walked into a strip-mall hair salon and pointed not at the “girl” styles taped to the wall but at Chachi’s feathered cut from Happy Days. “I knew what I wanted,” she recalls. “And fortunately, my parents were awesome. They never forced me into dresses. They let me be me.”

That defiance became its own kind of identity: a girl on the baseball team, short-haired, mistaken for a boy but unbothered by it. Looking back now, Sharp marvels at that child’s quiet conviction. “She was kind of a badass,” she says. “She knew who she was long before I did.”

On Tomboy, that kid meets the woman in her 50s who has weathered storms and found her footing in art. Together, they create a record that is as much a celebration of self as it is a continuation of the lifelong search.

Raised in a House of Sound

Maia Sharp’s gift is born of immersion. Her parents met in a high school band; her father, Randy Sharp, went on to a successful career as a songwriter and producer. By the time Maia was five, the family relocated to Los Angeles so Randy could sign his first record deal. “Music was just in the house all the time,” she recalls. “There were rehearsals, gigs, instruments everywhere. I’d crawl under the stage at shows and fall asleep.”

The family record collection was rich, but it was k.d. Lang and Annie Lennox who changed Sharp’s chemistry during adolescence. She took up the saxophone at 12, studied it through college, and only later began writing songs—at which point the pull was irreversible. By the mid-1990s, she was writing for others (Cher cut one of her songs in 1996) and releasing her own music, blending introspection with craft.

“I came as a writer first, not a singer who also wrote,” Sharp says. “It took a lot to get past my introverted nature, but songwriting was always the anchor.”

Maia Sharp’s Lessons in Belonging

If Nashville taught her anything, it was the futility of comparison. “As soon as you can shed your urge to compare yourself to other artists, you’ll go so much further,” Sharp insists. “It’s such an emotional wall.” For Sharp, that lesson carries even more weight. “There’s a big part of the population that doesn’t like me because of the fact that I’m gay, even though we’ve never met,” she says. “I had to learn to say: that’s not about me.”

Instead, she’s devoted herself to community: co-writing, collaborating, and serving as a mentor. Twice a month, she works with veterans through Songwriting with Soldiers, distilling their stories into songs in under three hours. She also teaches remotely for NYU’s songwriting program. “Those experiences remind me it’s about keeping the creativity flowing out into the world,” Sharp says. “That flow creates new relationships, new collaborations, new live opportunities.”

Her Music Is a Catalogue of Longing

Maia Sharp’s songs often wrestle with desire, loss, and the fragile balance between strength and surrender. “Backburner” warns of the costs of ego. “A Fool in Love Again” celebrates the risk of vulnerability. Her catalogue, like her life, is a study in paradox: grounded yet searching, steady yet fluid.

She laughs about being “the most single I’ve ever been,” but insists that openness remains her compass. “Everything is fluid,” she says. “That’s what keeps me centered. That’s what keeps the songs alive.”

For Sharp, Tomboy is not a culmination but another chapter in the unfolding. “There’s always a next thing,” she says. “What else could I be? What else can I say? What else can I learn? And maybe I’ll write a song about it.”

In her hands, songwriting is not a mirror but a compass. It points not to answers, but to movement—to the search itself. If confidence and humility can coexist anywhere, it is in that space: the perpetual becoming of an artist who refuses to stop asking.

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