The beloved 1998 rom-com “How Stella Got Her Groove Back” saw Angela Bassett — at the peak of her movie career — and the illustrious Whoopi Goldberg pack their bags and head to Jamaica with fresh-faced newcomer Taye Diggs, in his first film role as young, handsome islander Winston Shakespeare.
Back then, 27-year-old Diggs was best-known for originating the role of Benny in Jonathan Larson’s “Rent. The film also marked the feature debut for director Kevin Rodney Sullivan.
Also Read: Angela Bassett Set to Play CIA Director in 'Mission: Impossible 6'
The film, and book it was adapted from, captured black and female audiences in the late 90’s and early 2000s. Sullivan, who’s directed many episodes of TV since, as well as films like “Guess Who” and “Barbershop 2,” told TheWrap that people still come up