She portrayed Dina in the 1988 film School Daze and Whitley Gilbert-Wayne on the NBC The Cosby Show spin-off A Different World, which originally ran from 1987 to 1993.

Guy won four consecutive NAACP Image Awards from 1990 through 1993 for Outstanding Lead Actress in a Comedy Series for her role on the show.

Born in Boston, Massachusetts, to Jaye (née Resendes) and William Vincent Guy,[5] she was raised in the affluent historic Collier Heights neighborhood of Atlanta, Georgia, where she attended Northside Performing Arts High School.

In addition to her defining role on A Different World, she appeared in a 1991 episode of The Fresh Prince of Bel-Air as Kayla, one of Will Smith's girlfriends.

In 2002, Guy lent her voice to the PBS math-based animated series Cyberchase, playing Ava, the queen of the cybersite Symmetria, and made a cameo appearance on the Moesha spin-off The Parkers.

Guy played Roxy Harvey, a meter maid turned police officer and one of the core group of grim reapers around which the series was based.

In that program, Guy played Sheila "Grams" Bennett, the grandmother of Bonnie (Katerina Graham), who proved to be a descendant of Salem Witches.

During the following year, she appeared as Dominique La Rue in Harlem Nights starring Eddie Murphy (who also directed), Richard Pryor, and Redd Foxx.

In 2015, she appeared in the film Big Stone Gap with Ashley Judd, Patrick Wilson, Jenna Elfman, Anthony LaPaglia, Jane Krakowski, and Whoopi Goldberg.

[7] Guy has performed in several Broadway productions and national tours, including as Crow in The Wiz, Mickey in Leader of the Pack, Betty Rizzo in Grease, and as Velma Kelly in Chicago.

On April 6, 2009, Playbill reported on Guy's return to the stage, starring in the True Colors Theatre Company production of Pearl Cleage's Blues for an Alabama Sky.

[16] Blues came on the heels of Guy's held-over run in True Colors' Miss Evers' Boys, which co-starred TC Carson of Living Single.

[17] Guy directed the world premiere of I Dream in July 2010 on the Alliance Stage of the Woodruff Arts Centre in Atlanta.

Also in 2010, Guy was a member of the cast of the Alabama Shakespeare Festival and the Alliance Theatre Company co-production of Pearl Cleage's The Nacirema Society Requests the Honor of Your Presence at a Celebration of Their First One-Hundred Years.