A few weeks ago, while sitting on a porch here on the Vineyard, Jessica Ashley leaned back, closed her eyes and began to sing. Or rather, she belted out a few lines, totally absorbed in the music. Afterwards she opened her eyes and asked, “Do you know that one? My sister and I used to sing that one together.”

Her producer, her manager and a journalist sat in awe at what they had just heard coming from such a slender teenager still seated in an armchair.

Jessica had been on-Island for a few days, taking a break from the busy New York city scene and enjoying some sun and the first of two summer gigs on the Vineyard. She performed at the Pit Stop in Oak Bluffs during round one of her Vineyard vacations. She returns to the Island for a concert at the Old Whaling Church in Edgartown this Sunday, August 12.

Jessica’s manager, Johnny Woluewich, is no stranger to the Vineyard. His stepmother owns a house tucked away in Oak Bluffs where he still vacations every year. But the real driving force to bring the nineteen-year-old rising star to the Island was Paul Adler, who prides himself on his ability to spot talent.

“I don’t need minutes. I need seconds,” he said. “I saw her and said, that’s it.”

Jessica sat smiling as Mr. Adler explained the finer details of his behind-the-scenes job. When he laughed and said, “Artists themselves are generally not business people,” she nodded and added, “We’re not. Often we don’t know what we’re saying yes to.”

But it’s not as if Jessica hasn’t been trained extensively in the music world, both on and off-stage. As a kid growing up in Queens and later in Lynnbrook, New York, she played classical piano with her father and private teachers. In high school she played violin while her sister was trained in opera. Classical music was the accepted sound in the house, even though Jessica dabbled in Disney songs and pop music. She remained in New York for college, enrolling at New York University’s Clive Davis Department of Recorded Music, the same school many succesful musicians attended, including Lady Gaga and Elle Varner.

“I lived in Gaga’s dorm,” Jessica said. “I learned so much there. Literally every single mic and cable.”

But, as with many future stars who passed through those halls, the music world beckoned. Mr. Woluewich discovered Jessica on YouTube performing cover songs.

“YouTube has become an essential resource for artists to use for accessing an independent music market,” he explained. “I stopped what I was doing and went to meet her.”

He liked what he found. “Probably 99 per cent of people are in it for the wrong reasons — for vain reasons. I’m glad to be working with someone who’s doing it for all the right reasons,” he said.

Jessica has since worked with hit producers including Sean Garret, who also works with Beyonce Knowles, Nikki Minaj and Nikola Bedingfield, the sister of pop artist Natasha Bedingfield. Jessica also writes music, and her songwriting talents have already captured the affection of big names like pop star JoJo, who recorded a Jessica-penned song called Limbo.

Jessica is often compared to Christina Aguilera and Mariah Carey. “I like being compared to those women. But I want to bring my own take.”

But being a teenager, her own take still includes influences from home.

“My mom likes to be my stylist,” she said. “I can see it starting — she gets all excited and starts throwing out ideas, adding and altering clothes.”

On Sunday, Jessica will be performing with Sally Taylor.

“It’s the perfect way to pair the new with the old,” said Mr. Adler. “Well, Sally isn’t old, actually” he added, “But she’s been around.”

Ms. Taylor went on a hiatus from the music world when she became a mother, but is now returning to the scene. The concert will feature the resurgence of a familiar Island face along with the introduction of a new one, who over time will grow more and more recognizable.


Jessica Ashley and Sally Taylor will perform at 8 p.m. at the Old Whaling Church in Edgartown. Doors open at 7 p.m. Tickets are $40 and $70; and can be purchased at ticketsmv/kool. Call 508-645-3462.