I was lucky enough to join a small group of journalists for an interview with Lee about the original film and the updates. He told us that it was the sixth script he wrote while he was still living in his parents’ basement, and the thought that if this one did not sell, he might give up.

He said that Jeff Friday and Nicole Friday of the American Black Film Festival, the founders wanted to honor him and the cast for the 20th anniversary of its release, but because of the pandemic it was postponed and they got IMDb to televise it. “I asked the cast if they wanted to do it and they kind of all jumped at the chance to do so because the film was wildly respected, loved and beloved. We got together. It was a really good fun time. Lot of laughs. A lot of stories exchanged. Things I didn’t know. Things that they didn’t know. There’s a lot of great energy when we get together. I think it’s a testament to how the actors feel about the movie and about each other.” And we can look forward to another update on Peacock: “The Best Man: Final Chapters

Lee said he never planned that it would become a franchise.

My inspiration and impetus for writing “The Best Man” was the fact that I wasn’t seeing myself represented on screen. The people that I knew, Black American educated middle class aspirational people in movies and television to that point were very unrecognizable to me. Super stiff, clipped English, and devoid of cultural specificity. I said, “I love reunion movies. I love college movies.” College movies rather. I remember seeing “Waiting to Exhale,” which is four very distinct black women and they were all these unremarkable archetypal black men portrayed and I was like, “I want four Black men.” This is fully different and it will all be college friends and have different philosophies and what not and that was the kind of the impetus behind it. The fact that people really took to the movie is great and there was talk of a sequel back then but I didn’t want to be a one trick pony. I didn’t want to just tell one kind of story. I said, “If I’m going to revisit these characters,” which I was interested in doing but I want to do it like maybe 10 years later when the characters have a chance to live some life, and I had a chance to live some life and so that we could tell a fuller story. Not just be like, “What different story are we going to tell now that we just told a year ago.” A lot of time when they make sequels it’s a money grab. It’s like, “Oh. How do I what I did? How do I capture that magic again?”

One core element of the original film was a character’s writing a novel that exposed some of his friend’s secrets, so it was inevitable to ask Lee whether he based the characters on people he knew and how they responded.

It is funny too because the friends that thought they were those characters. I was like, “Well you were not exactly the person I was thinking of.” What’s great about it is that I took pieces from a lot of different people. I knew what I wanted for each of these characters and who I wanted them to be but nobody was a specific individual. They were just pieces of people.

We asked him about casting.

I think when we go to the movies there’s an aspirational aspect, a heightened reality, a little bit of an escapism as well, but also a place where we can say, “Oh like that I can relate.” People love seeing people get married. People love seeing beautiful people get married. And we had such a tremendous response in the acting community to the script. A lot of black actors weren’t getting that opportunity to play full people. Here was an opportunity for eight of them to play these roles. Not just to be the sidekick or the best friend or the one that’s packing the funny jokes or the sassy one or whatever. It was an opportunity for them to play real people and so the response was tremendous.
They were all very excited to take this on.

There was a real joy and opportunity for them to showcase themselves. They trusted the script. They trusted me. I wasn’t just like, “All right. Let’s read the lines.” We worked rehearsal for two weeks. Really let them dive into character and backstory and subtext. I think that was what they were all really excited about and all wanted it to be great. It was even more so for “Best Man Holiday” because the energy in Hollywood was in a weird place at that time where they weren’t really putting much stock into African American-cast movies.

We had to ask about “Space Jam: A New Legacy.”

I think it’s probably the coolest movie that I have ever done. I really like the movie. I like and care about the characters. I think it’s fun. I think it’s funny. There’s a lot to like about it.