<P> How Stella Got Her Groove Back is a 1998 romantic comedy film directed by Kevin Rodney Sullivan, adapted from Terry McMillan's bestselling novel of the same title . The film stars Angela Bassett, Taye Diggs, Whoopi Goldberg, and Regina King . The original music score was composed by Michel Colombier . </P> <P> Stella Payne is a very successful 40 - year - old stockbroker raising her son, Quincy, and living in Marin County, California, who is persuaded by her best friend from college, Delilah Abraham, to take a well - deserved, first - class vacation to Montego Bay, Jamaica . As she soaks in the beauty of the island, she encounters a handsome young islander, Winston Shakespeare, who is twenty years younger . His pursuit of her turns into a blossoming romance that forces Stella to take personal inventory of her life and try to find a balance between her desire for love and companionship, and her responsibilities as a mother and corporate executive . </P> <Ul> <Li> Angela Bassett as Stella Payne </Li> <Li> Taye Diggs as Winston Shakespeare </Li> <Li> Whoopi Goldberg as Delilah Abraham </Li> <Li> Regina King as Vanessa </Li> <Li> Suzzanne Douglas as Angela </Li> <Li> Michael J. Pagan as Quincy Payne </Li> <Li> Sicily as Chantel </Li> <Li> Richard Lawson as Jack </Li> <Li> Barry Shabaka Henley as Buddy </Li> <Li> Lee Weaver as Nate </Li> <Li> Glynn Turman as Dr. Shakespeare </Li> <Li> Phyllis Yvonne Stickney as Mrs. Shakespeare </Li> <Li> Denise Hunt as Ms. Thang </Li> <Li> James Pickens, Jr. as Walter Payne </Li> <Li> Carl Lumbly as Judge Spencer Boyle </Li> <Li> Victor Garber (uncredited) as Isaac </Li> </Ul> <Li> Angela Bassett as Stella Payne </Li>

Who played winston in how stella got her groove back