How Stella Got Her Groove Back was a hugely successful film from 1998. It is a romantic drama by the director Kevin Rodney Sullivan, based on the same titled novel. The casting in combination with a well crafted storyline made this movie a hit with modern viewing audiences. The story told in How Stella Got Her Groove Back centers around the character Stella, played by Angela Bassett. Stella is a stock broker by trade and a single mother raising her son in California. As she turns 40, Stella is talked into going on a much needed vacation trip to beautiful Montego Bay. The Jamaican holiday is an idea proposed by her good friend Delilah, whose role is played by Whoopi Goldberg. It seems like a simple enough beginning, but surprises are ahead.
As Stella and Delilah take in all the best that Jamaica has to offer, something quite unexpected comes along. Stella finds her self on a rendezvous with romance, but with a much younger man named Winston, who Taye Diggs is cast in the role of. Winston is 20 years younger than Stella, yet there is much to consider on Stella's end. What should she do? What can she do? What shouldn't she do? But most important of all, what will she do to have true love? How Stella Got Her Groove Back takes flight as the story evolves, from passionate love inspiring moments to the greater search for balance in a practical life.