“Terrifying, exhilarating, gratifying.” When asked to choose three adjectives to describe her career, that’s what actor Cheryl Singleton ’81 offered up. Singleton, whose most recent role was Calpurnia in To Kill a Mockingbird at the Gloucester Stage Co., was a theater major at Amherst, where she excelled as a stage manager. Her passion lay in acting, but the times weren’t in her favor. Unlike today, few productions at Amherst then featured nontraditional casting, so while she did some sketch revues, she was never cast in plays with parts ostensibly slated for white actors.
After graduation this Brooklyn native returned to New York to reach for a career on stage and screen. She landed a part in Spike Lee’s 1986 movie She’s Gotta Have It. Talk about a fiery cameo: Singleton starred in a nightmare sequence, playing a vengeful girlfriend who menacingly holds a lit match to protagonist Nola Darling’s mattress.
As Singleton acted more, she also kindled a prime reputation as a theater director and stage manager. But competence can be a curse. “If you’re a stage manager and you’re good, they want to keep you there,” explains Singleton. “I really had to stop and say, ‘OK now, I’m an actress and you need to think of me in those terms.’”
This led to a makeover move to Boston. She got a job at a financial services market research firm, where her people skills and stage manager talents converted winningly; she began as a receptionist and worked her way up to the publishing division, and then human resources, staying for 25 years.
Meanwhile, over the decades (often using her vacation time to do the shows), Singleton has made a name for herself in the New England theater scene.
She has acted with the New Repertory Theatre, The Huntington Theatre Co., Commonwealth Shakespeare Co., the American Repertory Theater, Providence Stage and more. Her stage credits include Chekhov’s The Seagull and Shakespeare’s Comedy of Errors, Lynn Nottage’s Intimate Apparel, Melissa Sanchez’s Sonia Flew, the transgender-themed theater piece Home and the six-hour historical epic The Kentucky Cycle.
Singleton has also done commercials and voice-overs, and she can sing, having appeared in musicals such as Rent and Passing Strange. Improv is also in her wheelhouse. At Musical Improv Boston, she has helped whip up three-act musicals on the spot (“so challenging and a ridiculous amount of fun”).
In addition, she coolly played Condoleezza Rice in David Hare’s Stuff Happens (a box office smash for the Zeitgeist Stage Co.) and hotly played Storm, the weather-commanding X-Men character, in the satirical Superheroine Monologues (“also a ridiculous amount of fun”).
In her online profile for StageSource, a networking site for the theater community in Boston, Singleton singles out her Wade Fellowship experience. She first learned about Harold Wade ’68, and Amherst’s history of African-American students, at her own first-year orientation. “That was a very important thing for us to be told that first week: ‘These are the people who came before you, and you should know that these are some of the things that happened, and you may encounter racism while you’re here. You probably will. It hasn’t left the campus.’”
During her 1990–92 fellowship, Singleton came to campus and spoke about the business of being a theatrical professional, “because that’s not something that we talked about in the major when I was there,” she says. “I wanted them to know you really need to think about it as a business like any other.”
Singleton has hosted alumni-mentoring events for students in Boston, too. But the Wade experience is closest to her heart: “I was just very proud of being chosen and being thought of as someone who could carry that mantle.”