When the film “The Best Man” was released in 1999, featuring a cast of young, up-and-coming, attractive Black actors including Taye Diggs, Nia Long and Terrence Howard, it wasn’t just a box office hit but also a fresh perspective on film, following the ups and downs of friendship, careers and love through the lens of young Black professionals.
“I remember reading that script and feeling, ‘Oh, this is something I’ve never seen before. Black people represented in this way,’” recalled Diggs, who plays Harper, a successful author. “I had never seen a project where I saw myself.”
Morris Chestnut, however, says at the time he was just thankful for the work and everything that came after is a welcome bonus.
“As an actor, you’re glad to just get a job. You want to work. You want to get a job that pays,” he said. “Starting out, you do things that no one ever sees. I had no idea it would still be around to this day.”
Director, writer Malcom D. Lee reunited the cast for a 2013 sequel “The Best Man Holiday” which was also a success. Now, he’s wrapping up the story with an eight-episode limited series on Peacock called “The Best Man: The Final Chapters.”
Originally Lee envisioned possibly two more films to tie up the stories, but he says with a series, there’s more real estate for storytelling. He used some of his ideas for movie sequels in the show and enjoyed being able to stretch that further and find additional stories for the characters.
“You get a little bit more time to just expand on their story and dig deeper into their home life, their career life, their personal struggles and triumphs. (The films) were the impetus, but it grew into something else.”
Regina Hall says the series gives each character an arc “as opposed to feeding one story, the collective. But to be honest, I would have enjoyed any iteration of it. I would have enjoyed it as a film.
“For me, it’s just the characters and being honest to those relationships that they have and the love they have for each other and their trials and tribulations.”
More time was a welcome idea for Melissa De Sousa, who wanted her role of Shelby, a bossy reality TV star, to be fleshed out.
“Not only was it necessary, it was requested. I said, ‘Listen, if we’re going to do this, it can’t be the same thing over and over. You have to see all sides of her. You have to show why she is the way she is. You have to see a real woman with emotions and struggles, and fears,’ and they did that.”
To transition to television Lee tapped “Insecure” writer and executive producer Dayna Lynne North to be co-showrunner.
“I’ve been a fan of the franchise for my whole adult life. I liken it to going from being in the stands, watching your favorite team, to LeBron (James) or somebody being like, ‘Hey, you, fan. You want to come down and play with us, you know what I mean?’ That’s really what it felt like,” said North. “It felt like going from my cheap seats to down on the field. .. It’s really been an honor and super fun because I’ve loved these characters from the moment that I met them.”
While each character in “The Best Man” franchise weaves a tangled web, the catalyst for drama in each iteration of “The Best Man” is Harper’s novel, “Unfinished Business.” Inspired by his friend group, the book reveals some explosive secrets, including how Harper once had a one-night stand with his best friend Lance (Morris Chestnut’s) fiancee.
In “The Best Man Holiday,” Lance is still bitter about revelations from the book. In the series, Harper could see “Unfinished Business” made into a film. He wants to get in front of any potential drama and get his friends’ blessing for the project, and what better time to ask than at a destination wedding for their friend Quentin (Terrence Howard.)
Lee calls Harper’s book “the magic prop.”
“I was very strategic in the first ‘Best Man’ with trying to create something that was a hot button thing. I called it a magic prop because it kept on getting passed around to the friends and then it got into the wrong hands.
“The ‘Unfinished Business’ book certainly is causing drama this time around as well. Even though it’s not what the series is about, it’s about these folks and about their relationships, but it’s a good engine.”