Angela Bassett Remembers Casting Taye Diggs for ‘How Stella Got Her Groove Back’: ‘He Had to Fulfill the Fantasy’

Tribeca 2023: Bassett and director Kevin Rodney Sullivan reflect on the classic comedy’s legacy at 25 years

Angela Bassett speaks onstage during a Q&A at the “How Stella Got Her Groove Back”
Angela Bassett speaks onstage during a Q&A at the “How Stella Got Her Groove Back” screening during the 2023 Tribeca Festival (Credit: Dominik Bindl/Getty Images)

“How Stella Got Her Groove Back” star Angela Bassett and director Kevin Rodney Sullivan didn’t hold back Saturday night at a 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. During a steamy scene of Stella and Winston in the shower, for instance, only Diggs is nude. 

“I knew that it was important for me to make the love scenes from a woman’s point of view,” Sullivan said. “It was not Winston’s story. It was Stella’s story. And it wasn’t and it shouldn’t be clouded by my maleness, my gender deficiency. So I thought of Angela as my partner. We were partners. We made the movie together.”

“So I developed some ideas around the love scenes,” he added. “And I storyboarded them and I shared them with Angela so that she could see exactly what I wanted to do and we could talk about it and we [could] be specific… In that process, she definitely gave me input that ultimately made it to the screen.”

Though romance is at the heart of “How Stella Got Her Groove Back,” the other key component of the film is friendship — and Stella would be nothing without her Deliliah, as played by Goldberg. The quintessential best friend character, played with marvelous wit and depth by the heralded actress, is the glue that ties the movie together and certainly gives it a ton of heart. According to Sullivan, he initially went to the studio to float the idea of casting Goldberg initially, but when he learned that she wasn’t attainable for the project, he took matters into his own hands.

“I went to her house and had a conversation with her. And she said yes,” Sullivan revealed. “So that was really the turning point in some ways for the comedy of the movie because I felt like someone as funny as Whoopi would elevate everything comedically — and of course she did.”

Goldberg elevates the film’s drama, as well. In fact, she is arguably the dramatic core of the movie. Sullivan seemed to agree, because he further opened up about how the heart-wrenching hospital scene between Stella and Delilah was crafted. 

“It happened not from what was on the page, but from a rehearsal we had on a Saturday. We went onto that little set that had been built, [Angela] and me and Whoopi, and made up most of what you saw,” he explained. “Cockeyed Charlie, the dancing, Angela’s idea was ‘Row, Row, Row Your Boat.’ All of those moments were created in a rehearsal a couple of days before we shot it. It was one of the most beautiful Saturdays of my life. I mean, can you imagine? To be with the two of them and let’s just make something happen… It’s my favorite scene in the movie. What they did there was just extraordinary.”

Finally, further reflecting on the film’s legacy 25 years later, Bassett gave due recognition to author Terry McMillian, who wrote the novel “How Stella Got Her Groove Back” is based on. McMillian’s work has long been impactful for Black women; Bassett even starred in another adaptation of her work called “Waiting To Exhale” in 1995. 

Touching on McMillian’s legacy in Black literature and what the writer did for her portrayals of Black women, Bassett said, “She ushered in this moment through her books of Black female strain and assuredness in what you want and what you need in spite of, regardless of, what society says. I wish she could be here with us today. But we love her, and she continues to do that.”