Lily Meola, Home for the Holidays

Weaving a tapestry of grace from the shreds of a grieving heart

Maui singer-songwriter Lily Meola could give a master class in discovering the beauty and grace within the paralyzing sadness of losing a loved one. Through her emotional appearances on “America’s Got Talent!”, she already has. At age 28, Meola is more familiar with grief than she ought to be. She was a rising star in the music world with a record contract in hand and the support of collaborators like country music legends Willie Nelson and Kris Kristofferson when her mother was diagnosed with cancer and her world fell apart. 

Photo by Vivian Kim

Lily’s mother Nancy had been her biggest cheerleader as she developed her talent and found her sultry and soulful voice. Now an inoperable tumor was constricting her pulmonary artery. A longtime assistant to talent manager Shep Gordon, her passing was felt across the local music community.

“Even though she’s not here, physically, I’m still chasing every day to try and make her proud,” Meola told MauiTimes during a rest stop on her fall tour of the deep South. “It’s been really difficult and what I’m finding is that chasing after stuff and going on this tour and just continuing on is how I communicate with her.” 

The two held a deep mother-daughter bond, strengthened by their mutual love of music and butterflies. “I talk to my mom all throughout the day every day,” said Meola. “I still feel lost, but you’ve got to make do with what you’ve got and try to keep a smile on my face.” 

“America’s Got Talent!”

When a last-minute opportunity to audition for “America’s Got Talent!” came up last spring, Meola wasn’t quite ready for the limelight, still mired in a lingering depression brought on by her mother’s death. But she threw caution to the wind and went for it, choosing a heartfelt, inspirational original song, “Daydream” for her first audition. The song, which exhorts the listener not to let go of their youthful ambitions, was a favorite of her mom’s. 

Simon Cowell’s questioning before the performance led to Lily revealing the loss of her mother, and with it, the loss of her first major label record deal. The tearful, heartbreaking performance made her an immediate audience favorite and earned her the Golden Buzzer from judge Heidi Klum.

“It was a bit more of a sob story than I would have liked,” she said of the way the show focused on her mother’s passing. “I guess being super honest and spilling my heart out might be uncomfortable for me—and maybe for some viewers, too—but it’s a moment to connect.” And connect she did, winning thousands of new fans literally overnight. 

“Honestly, I don’t think I did well,” she admitted. “I’m all about showing myself in my rawest forms, but I lost it during that performance.” Her emotion was genuine, and intense.

“You know when you’re, like, crying and you have a lump in your throat? I felt like I didn’t hit one right note the whole song,” she said. “I was so choked up and had snot dripping from my nose. It was so bad! But another day arose and I’m still kicking and people still understood the message and felt connected to it, and that’s all that matters.” 


For Meola’s second performance, on the program’s fourth live show August 30, she chose an original song she had written about her mother’s passing called “Butterfly,” its bittersweet chorus ending with the words, “I know we’ll meet between Heaven and the sky, I’ll try, I’m gonna try to find the good after goodbye.”

“After going on the show, I kind of felt inspired again. I was in a moment of kind of needing to take my own advice,” she explained. “It wasn’t just to inspire other people, but to inspire myself, too. I felt so much love after the show it got me back in the studio writing again.”

Meola and her older brother, Matt, comfort their mother, Nancy, as she battles lung cancer. Courtesy Lily Meola

“Butterfly” was the first song Meola had written since her mother’s death. “It was just so healing and really helped me kind of understand where I was in my emotions and stuff,” she explained. “So, it felt like the natural thing to do, rather than a song about a heartbreak or something.” 

The story behind “Butterfly” is a beautiful one. When she was little, Lily’s mother would collect caterpillars from the garden and they’d watch them pupate and emerge from their cocoons as monarch butterflies. It was a hobby the two shared throughout her childhood. 

During the COVID-19 pandemic, family members weren’t allowed into the hospital where Nancy went for treatment, so Lily found herself absent from her mother’s presence for the first time in months. “I went upcountry, and it was kind of weird to be away from her,” she recalls. “I ended up stumbling across some milkweed, which is the plant that hosts the butterflies. I was so excited, I said ‘Oh, my gosh, I’m going to bring some caterpillars home to mom and we’ll watch the butterflies grow, like we had done in the past.’”

She brought the branch home and put it in a vase and the two watched the little caterpillars grow until they formed cocoons. “The first one hatched just 20 minutes before my mom took her last breath,” she explained. “It’s like it hatched while she was transitioning. It was just such a beautiful moment in such a tragic moment. Then the day that they took her body, our first day without her, the next butterfly hatched and it stayed with me and my brother for what seemed like hours.”

Despite a beautiful performance of “Butterfly,” Meola didn’t garner enough viewer votes to continue in the competition, but an online survey the following day found that 48 percent of those polled felt like she had been robbed of a spot in the finals.

“Just thinking back on it, I think, ‘Wow, I can’t believe I actually did that.’ I stepped out of my comfort zone,” she reflected. “But I’m really grateful for it, even though it pushed me really emotionally.” She’s tripled her social media following and gets recognized by strangers, now.

Jazzy roots

It was her mother’s love of jazz that gave Lily her start in music. “She loved Ella Fitzgerald and Aretha Franklin and Louis Armstrong and all these old jazz standards,” she said.

Lily thinks she was only about six when she first performed for an audience, and 10 or 11 when she landed her first job as a vocalist. 

“I remember my first paid gig was at the MACC (Maui Arts and Cultural Center) and I couldn’t believe it,” she recalls. Her mother had landed her the gig, singing in the courtyard before a show. “They gave me a check and I was like, ‘that means I’m a professional,’” she said with a laugh. 

Meola got even more serious about having a music career after she landed the lead in a high school musical, portraying Dulcinea in “The Man of La Mancha.” “It’s really funny. I was so bad!” she said of the performance. “I found the video of it recently and I was like, ‘what the heck was I thinking?’” Mom promptly enrolled her in voice lessons. 

She eventually landed a weekly gig singing at Café Des Amis in Paia, where the old outlaw Willie Nelson was so moved that he invited her to record with him. 

Befriending Willie

“Our families knew each other,” Lily explained. Her brother, pro surfer Matt Meola, went to school with Willie’s sons, Lukas and Mikah, which led to Nancy becoming good friends with their mother, Willie’s wife Annie. “Annie would come to my shows, and occasionally she would drag Willie along,” said Meola. “So, one day he sat in and we sang ‘Crazy’ together.”

After her set, Willie handed her a napkin with a list of song titles scrawled on it and simply said, “If you’d ever like to record any of these, let me know.” 

Photo by Vivian Kim

Sadly, a bad sound board corrupted the files from their session together, rendering them unusable, but the friendship led Nelson to ask Meola to appear on his 62nd studio album, “To All The Girls…”, a collection of duets with female singers on which she joins Willie for the soulful, heartbreaking ballad, “Will You Remember Mine.” The album put young Meola in the company of Dolly Parton, Roseanne Cash, Emmylou Harris, and Loretta Lynn.

Their collaboration led to an invitation to join Nelson on tour, followed by duet performances at several Farm Aid benefit concerts over the years. Now if they find themselves performing in the same part of the country, Meola is often invited to open for Nelson and join him onstage for a song or two.

She found another mentor in Jackson Browne, whom she met at a benefit concert in Oregon. Browne felt that Meola was ready to begin crafting her own songs and told her, “Next time you’re in L.A., come over to my house and I’ll teach you everything you need to know about songwriting in one sitting,” she recalled. “So, I’ve sent him some songs that I’ve worked on and he really listens to every line, and…gives his two cents. It’s really cool. For such an incredible songwriter to listen to such a newbie’s work is pretty exciting.” 

Meola released a solo album titled “They Say” in 2016—which included duets with Nelson and Kristofferson—but has since cast it aside because the songs were not her own. “I threw that record away, because that was before I really started writing,” she explained. After I found my voice and knew what I wanted to say, I said ‘this isn’t me.’ 

“I need to represent myself in the way that I want to and put out songs that came from my heart.” A second “debut” album of all original songs is in the works. It might have been released sooner had the representative from Interscope records who signed her stuck around. But he moved to Warner Brothers, and being under contract, Lily couldn’t follow him there. So, she languished until Interscope abruptly canceled her contract, just as her mother took ill. 

In March 2016, Rolling Stone magazine listed her among their “10 new country artists you need to know,” but Meola doesn’t like to be pigeon-holed. “It’s funny, I don’t really think of myself as a country singer,” she asserted, despite being associated with Nelson and Kristofferson. “I mean, there’s part of me that feels I have a bit of country soul in me, and in parts of my voice you can hear it, but I’d say more of a singer-songwriter and pop singer. I don’t like to limit myself.”

Homeward bound

Meola has been living in Encinitas, just north of San Diego, as she pursues her music career in California, but she still calls Maui home “forever and forever.” Her wing-foiler father Gary and pro surfer brother Matt seldom leave the island.

She spent most of the fall on a 20-city U.S. tour opening up for folk rocker Ray LaMontagne. Two members of her all-girl Maui band have joined her on tour, Olivia Morreale on keys and Tina Hughes on guitar. Having them along helps to keep Meola grounded. 

“The girls I’m with are so sweet, and we obviously have a lot in common, she said. “We’re all three female musicians hustling, trying to make it in this world.”

Her boyfriend, Forrest Dein, joined the tour for a few days, between hosting events for his hard kombucha business, Juneshine. She keeps in touch with friends and family on Maui as best she can. “FaceTime is my best friend,” she declared. 

But it’s still not easy knowing that her biggest cheerleader is no longer by her side. “Obviously I would do anything and everything to have her back here,” Lily said, “but I have no control over that so I’m just trying to make her proud.”

Dan Collins