A booming voice filled the Ogunquit Playhouse in Maine, posing a question to the young singer onstage. “What are you going to sing for me, Jenna?” The voice belonged to Kara DioGuardi, former “American Idol” judge and organizer of New England Sings, an annual competition held at the Playhouse. The question was addressed to Jenna Holiday, then 16, who had been invited by DioGuardi to perform in the competition after a friend of DioGuardi’s sent her a video of Holiday singing.
Holiday replied that she planned to cover “Brazil” by Declan McKenna. When she performed the song, the crowd sang along and cheered her on. By the end of the night, Holiday had been crowned the winner of New England Sings 2017 by audience votes.
“It definitely changed my entire perception of myself as a vocalist,” Holiday said, speaking by phone from Los Angeles. “Up until that point, I wasn’t a singer. And then suddenly, I was, because I won a singing competition. Suddenly I realized that my voice was another skill I could use.”
From then on, DioGuardi became a mentor to the Andover native. The original prize for the winner of New England Sings was a chance to take a free class at Berklee College of Music. However, DioGuardi had other plans for Holiday. She told the teen she didn’t need more training and instead sent her to Los Angeles to meet industry professionals and future collaborators. A few months after the trip, DioGuardi signed Holiday to her publishing company, Arthouse Entertainment.
Now 19, Holiday released her third single “Egoist,” a song that explores the line between romance and self-love, on March 27 under Arthouse.
“Finally, we’re in the process of preparing for another release, then another release and I don’t think it’s going to stop from here on out,” Holiday said. “I feel like all my hard work over the past couple of years is actually going to come to fruition.”
Holiday moved to Los Angeles full time after graduating early from Andover High School in 2018. “I think it’s an essential part of what I’ve had to do, and it’s given me a lot of life experience I wouldn’t have had without moving out so young and going into an industry that I barely understand,” she said.
Though navigating the industry required a learning curve, writing songs didn’t. Holiday said she has been telling stories through music for as long as she can remember. She recalled a memory from third grade of herself and a friend writing a silly song inspired by “High School Musical.”
For a while, she never shared her songs with anyone unless specifically asked to. When she was 15, she posted a few lyrics she felt especially proud of on her Twitter account. The lines gained traction on the platform, prompting Holiday to upload a video of her singing them. And her Twitter audience went crazy for it. After working with family friend and producer Dave Ingham, Holiday debuted that song as her first single. Titled “21,” the song has had more than 1 million streams on Spotify.
“The mentality I’ve developed about it is if I’m good enough and I work hard enough on my own talent, then I’m going to be wanted,” Holiday said. “People are going to notice that.”
After “21” got attention on social media, Holiday went on to cover Linkin Park’s “Heavy” at Red 13 Studios in Framingham with singer Blayk. Through mutual friends at the studio, the resulting video of the cover caught DioGuardi’s attention initially. That song was the only professional video Holiday had made until recently when she traveled to Nashville to shoot “Egoist.”
Holiday’s team chose an old mansion for the setting of the music video. “My whole life, me and my brother would just make stupid music videos because we were kids,” Holiday said. “Now suddenly, there’s someone else holding the camera.”
Adding to the list of credits the young singer has already accumulated, she co-wrote “Unstoppable” with rock band New Politics in 2019. The song, Holiday’s first professional writing credit, has since been licensed for use by the NFL Network and a slew of TV shows including “American Idol” and “Good Morning America.”
Drawing inspiration from Doja Cat, Billie Eilish, and Lorde, Holiday hopes to break boundaries, hone her craft, and assert her independence as a pop artist. “I really want to start bringing attention to detail back into the spotlight,” she said. “I want to challenge people’s perspectives of what pop music can do and what pop music can be.”
When venues reopen, Holiday plans to perform in Los Angeles and dive into directing and producing her own music videos for future releases. In the meantime, she’s gone back to where she started, writing lyrics and adding to her catalog of 100 original songs.
“I have so much fun when it’s just me and a producer and I get to just explore my mind, and no one gets to sit there and reel me in,” Holiday said. “That’s really why I do it.”