The original Dreamgirl made an appearance on Island this weekend.
Jennifer Holliday, who originated the role of Effie White in the hit 1981 Broadway musical Dreamgirls, gave a talk Saturday at a private Oak Bluffs fundraising event for the Boston Arts Academy Foundation. Ms. Holliday is the 2026 music honoree for the foundation, which funds the only public arts high school in the Commonwealth, and will accept her award on Oct. 22.
“While talent is easily distributed, opportunity is not,” said Denella J. Clark, Boston Arts Academy Foundation president and CEO, in a conversation with the Gazette Saturday. “It takes people like Jennifer Holliday... [to] keep the arts in Boston Arts Academy and make those opportunities possible.”
At the home of foundation board member Raynya Simmons and her husband Omar Simmons, Ms. Holliday sat down with Tony-nominated producer and arts advocate Giselle Byrd to discuss her career.
Dreamgirls chronicles the journey of the Dreamettes, an all-Black, all-female R&B trio from Chicago, as they navigate the music industry of the 1960s and 1970s. Ms. Holliday was only 20 when she became a Broadway sensation as the resolute and vocally gifted Effie, a role that would earn her a Tony and a Grammy.
But before Dreamgirls hit New York, the show ran its out-of-town previews in Boston, the city Ms. Holliday ultimately credits with launching the project.
“If it was not for Boston, then Dreamgirls definitely might have opened... but not with the great awards and the fanfare,” she said.
In Boston, it became clear that Ms. Holliday’s signature number, And I Am Telling You I’m Not Going, was so powerful that it had to be moved from the middle of the first act to the very end. Otherwise, standing ovations for her performance would have interrupted the flow of the show.
“Those ladies in their blue rinses on Wednesday afternoons would not let me off the stage,” she said.
Despite finding success so young, Ms. Holliday said her career stalled out by the time she was 27. The music industry was moving away from the kind of music she wanted to make, and her label was critical of her body. Music video directors either wanted to stretch footage of her to make her appear thinner or hide her in a shadowbox.
Eventually, her label dropped her, and she filed for bankruptcy.
“I couldn’t even afford to be Jennifer Holliday,” she said.
But after securing a role on Ally McBeal in 1998, she was able to reenter the mainstream.
“I was reintroduced to the world, and I started working again,” she said. “What if I had given up?”
Chasing dreams, Ms. Holliday said, often means facing rejection and failure. But she warned that not going after what you want, means someone else will beat you to it.
“You have to make a decision... to keep showing up,” she said. “Not only do we have to show up for life, but we have to show up for what it is that we want out of life.”
Ms. Holliday closed the event with a surprise performance of A Dream Out There With Your Name On It, a ballad from her 1991 album, I’m On Your Side.
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. Now, she’s working on a new album called Dream Woman, an ode to the role that made her famous and how far she’s come.
“I’ve been through so much,” she said.
Ms. Holliday confirmed she hadn’t planned to serenade guests — not until it became clear how much the Vineyard crowd cared about the cause. She only informed one crucial person beforehand.
“I snuck the music to the DJ,” she said.
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