The story of how 23-year-old singer-songwriter Lily Meola went from being a jazz-loving kid performing covers at local cafés on her native Maui to an artist-on-the-verge reads like a rock and roll fairytale. It involves her being mentored by super-producer Bob Rock, touring with the likes of Willie Nelson, being taught to write songs by Jackson Browne, and duetting with Steven Tyler, Kris Kristofferson, and Sammy Hagar.

But Meola, a charmingly laid-back, beach-loving Maui girl, is way too humble to trumpet such connections. Not to mention that to her, these music legends were just friends of her mom Nancy’s boss, legendary manager Shep Gordon. Ask Meola about the time Hagar called her up onstage to perform an impromptu number at one of Gordon’s star-studded parties, and she brightens at the memory, exclaiming, “Oh, yeah! Well, that’s just a typical night at Shep’s house,” she says, neglecting to mention that the drummer backing them was Mick Fleetwood (because that’s just a normal thing that happens), and that the performance aired on Hagar’s web series Rock and Roll Road Trip. “I didn’t see my upbringing as anything out of the ordinary,” she says, “but I do understand now that it was special.” 

What Meola remembers most about her childhood was falling in love with music. “I think the reason it happened is because my mom would play all this awesome, classic shit, like the old jazz standards,” she says. “Ella Fitzgerald and Joni Mitchell were my idols, as well as Nina Simone, Billie Holiday, Frank Sinatra, Cat Stevens, and James Taylor.” At age 11, after landing the lead in the Haleakala Waldorf school production of Man of La Mancha, Meola felt some vocal coaching would be helpful. “I knew singing was what I wanted to do,” she says. “Well, there was a minute where I was like, ‘Maybe I’ll be a hairdresser,’ because I was giving my friends haircuts in the bathroom at school, but the play did begin the artist journey for me.”

By middle school, Lily had landed a weekly show at Café des Amis in Paia where she performed Joni Mitchell and Carole King covers as well as some old jazz standards. Family friend Annie D’Angelo, began coming to see Meola perform, sometimes bringing her husband Willie Nelson. One night Willie sat in with Meola on Patsy Cline’s “Crazy.” “After the show, Willie handed me a napkin with a few song titles written on it and said, ‘Would you like to record any of these?’" Meola recalls. “He asked me if I wanted to be on his duet album. I was like, ‘Hell, yes.’" 

Meola duets on “Will You Remember Mine,” on Nelson’s 2013 album To All The Girls… and has performed with him at his annual Farm Aid concert each year. She has also toured with Nelson and his musician sons Lukas and Micah. (Meola's brother, pro surfer Matt Meola, was in a home-schooling program with them, which led to friendship between the two families.) “Willie is the most genuinely nice human on the planet,” Meola says “and he works harder than anyone I know.”

As she continued on her path to becoming an artist, Meola also spent time in the studio with producer Bob Rock, whose daughters she grew up with, and who helped her land a development deal with Verve Records after she wowed then-label head David Foster, though a recording contract didn’t materialize. “I was 17,” Meola says. “I just wasn’t ready.”

Then a few years ago, Meola found herself performing on the same bill as Jackson Browne at a charity event. “It was in Bend, Oregon, and we were both staying at the same house,” Meola says. “Jackson said, ‘Do you write?’ and I was like, ‘No, I don't really know where to start.’" He said, ‘I can teach you everything you need to know about songwriting on the piano in one lesson.’ And I said, ‘I'm taking you up on that!’” The next time Meola was in L.A., she visited Browne. The two sat at his piano and talked for a long time, and he played her songs he was working on. “He taught me to use one legal pad for each song,” she says, “so you don’t get lyrics for different songs confused. Then he gave me my own golden pad.”

Meola had thought about writing songs before meeting Browne, “but I honestly didn’t think it was possible,” she says. “I have dyslexia and a hard time paying attention. School was really hard for me -- writing, math, everything. So writing a song just seemed impossible. How could I do that?”

Fast-forward to today and Meola has been in the studio with various co-writers crafting the bluesy, soulful pop songs that will make up her debut release for later this year. “This past year has been like writer speed-dating!” she says. “It’s meeting new people almost every day.” Still in the early stages, the music matches Meola’s sophisticated sensibilities with a soulful intensity and blend of live instrumentation and gritty, modern-sounding production. Though her rich, supple voice has led to comparisons to Amy Winehouse and Adele, Meola is currently experimenting and finding her own sound through songwriting. “I believe less is more,” she says. “Just stay soulful and try and write about something you’re passionate about.” The songs, some of which are about loss and grief, while others are about living in the moment and enjoying our time here on earth, are infused with Meola’s endearing vulnerability and fierceness of spirit.

“Turning words into music is a huge accomplishment,” Meola says. “I also just like being able to say what’s on my mind.”

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Responsible Agent Corrie Christopher Martin

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