Tribeca Festival screening and talkback celebrating the movie’s 25th anniversary. Going long in a lively discussion moderated by Torell Shavone Taylor at the SVA theater in New York City, the two got candid about choreographing Stella’s sex scenes, casting at 20-something Taye Diggs to “fulfill the fantasy” and trusting an Oscar-winning scene partner like Whoopi Goldberg to hold the film together.
The beloved romantic comedy from 1998 stars Bassett as Stella Payne, a 40-year-old businesswoman who takes a well-needed vacation in Jamaica, only to fall for a handsome man half her age, Winston Shakespeare (Diggs).
Bassett explained that casting Diggs as Stella’s lover for the movie was key to its success — and that it was a tight race between he and two other actors. “It was down to three that we actually put to film [for screen tests],” Bassett recalled of the actors going out for the role.
Sullivan chimed in: “We won’t say any names, but almost all of those guys became famous.” “When it came down to it, Taye had, across the board, the attributes that are needed,” Bassett said. “And the foremost needed was he had to fulfill the fantasy.” Speaking to Stella’s fantasy, Sullivan knew it was important for him to capture her love affair with Wintston from a female perspective.
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