Winston portrayed Nell in musical The Me Nobody Knows (1970−71)[5][7] before landing the role of Sylvia in Shakespearean comedy The Two Gentlemen of Verona (1972−73), replacing Jonelle Allen.
Winston then appeared as Cleo in musical I Love My Wife (1979), with Lawrence Hilton-Jacobs playing her character's husband.
[12] She co-wrote the musical Nativity: A Life Story alongside James Stovall, which has been performed frequently since its inception.
Winston's most notable character was Valerie the Librarian, the girlfriend of Easy Reader (portrayed by Morgan Freeman).
[22] For her work on Homefront, Winston was nominated for an NAACP Image Award for Outstanding Actress in a Drama Series in 1994.
[28] In 2001, Winston received her second NAACP Image Award nomination, in the category of Outstanding Supporting Actress in a Comedy Series as Margaret.
Following her run on Becker, Winston made guest appearances on ER, Cold Case, Castle and Mike & Molly.
In film, Winston portrayed Mrs. Todd in Beverly Hills Cop III (1994),[1] Simone in Jackie Brown (1997)[29] and Angela Russel in True Crime (1999), the latter opposite Clint Eastwood.