‘The Best Man’ director revisits film 24 years after its release

Screening and talk with Malcolm D. Lee held at MFA Boston

I’m reminded of a few things when I watch ’90s films. Relaxers and thin eyebrows were pervasive. The soundtracks always make me want to dance. And Terrence Howard has been playing ne’er-do-well characters for quite some time. None of this is more apparent than in the 1999 film “The Best Man,” starring Taye Diggs, Nia Long and Morris Chestnut, with Howard in a supporting role. The film’s release 24 years ago was Malcolm D. Lee’s directorial debut and a hit with Black audiences.

On Nov. 3, the Museum of Fine Arts hosted a screening of the film in partnership with the Roxbury International Film Festival (RoxFilm). A conversation and audience Q&A followed with Lee and RoxFilm’s artistic director, Lisa Simmons.

“The Best Man” director Malcolm D. Lee PHOTO: UNIVERSAL PICTURES

“The Best Man” follows Harper (played by Diggs), a writer whose autobiographical novel, “Unfinished Business,” inevitably dredges up unfinished business and creates problems for his group of college friends. The group gathers for a few days before the wedding of their mutual friends Lance (played by Chestnut) and Mia (played by Monica Calhoun). Tensions and truths come to light, and by the end of the film, the unfinished business is resolved.

Lee is known for comedic ensemble movies like 2017’s “Girls Trip.” He was raised in a family of musicians, actors and filmmakers, including cousin Spike Lee, whose production company 40 Acres and a Mule produced “The Best Man.” As a result of his early introduction to the film business, Malcolm Lee is keenly aware of the business of Hollywood.

During his conversation with Simmons, Lee remarked that he knew a film like “The Best Man” could be made because it was coming on the heels of other African American films like “Soul Food,” “Love Jones” and “Waiting to Exhale.” Plus, wedding movies are profitable. “‘The Best Man’ was the right script at the right time,” Lee said to the audience. In the entertainment industry, where trends leave just as quickly as they come, timing is everything.

Lee also said he wasn’t as interested in positive images of Black people in film as “fuller images.” Unfortunately, the director missed the mark with some of his characters in this regard, especially the female ones. Harper’s girlfriend Robin, played by Sanaa Lathan, has little backbone and little character development; the actress Melissa De Souza, who plays the resident shrew Shelby in the film, told Refinery29 in a January 2023 interview that her character lacked depth.

Lee did tell audiences, “I didn’t consider it a movie for women. I said, ‘I’m making this for dudes, making this for the brothers.’” However, as press for the film increased, people asked if the film was for women or men. Over the years, many women watched the movie and continued with the franchise. Meanwhile, the actresses in the cast advocated for more complexity in their characters.

During the audience Q&A, someone asked Lee what he disliked the most about the entertainment industry. He said, “I wish there wasn’t such a pressure to make money, but I don’t want to see everyone’s inner demons, either,” which drew a few chuckles. Lee also shared that he originally had Will Smith in mind to play Harper and Jada Pinkett Smith to play Jordan after reading an interview of Smith where the actor discussed the dearth of roles in Hollywood for Black actors and actresses. Other actors that didn’t make the cut were Regina King, Michael Jai White and Steve Harris.

At the end of the conversation, Lee shared that he wanted to show the humanity of Black people, especially educated Black people. At the time, he felt there wasn’t enough on-screen representation of the African Americans he knew and grew up around. He wanted his films to change that.

“That’s my whole mission,” he said, “to normalize Black life in America.”