“It takes people like Jennifer Holliday... [to] keep the arts in Boston Arts Academy and make those opportunities possible.” Despite finding success so young, Ms. Holliday said her career stalled out by the time she was 27. Chasing dreams, Ms. Holliday said, often means facing rejection and failure. After the event, Ms. Holliday told the Gazette she was happy to be on the Vineyard, where she had spent some time in her younger years. Ms. Holliday confirmed she hadn’t planned to serenade guests — not until it became clear how much the Vineyard crowd cared about the cause.