How "The Best Man"'s Cast Are Saying Goodbye to Their Franchise 20+ Years Later

It's been 23 years since fans were introduced to Malcolm D. Lee's "Black Pack" in his 1999 debut film, "The Best Man." Now, the cast — including Taye Diggs (Harper), Morris Chestnut (Lance), Nia Long (Jordan), Sanaa Lathan (Robin), Melissa De Sousa (Shelby), Terrence Howard (Quentin), and Regina Hall (Candace) — are bidding farewell to their cult-classic franchise with Peacock's "The Best Man: The Final Chapters," an eight-part limited series that follows the college friend group in their older years as they navigate their evolving relationships and past grievances.

"It's an opportunity to embrace them, see a reflection of themselves, and have some great nostalgia flowing."

The backdrop of the show is, of course, Harper's infamous novel "Unfinished Business," which gets adapted into a movie in the series, providing the perfect full-circle moment to close the book on "The Best Man." "'Unfinished Business' was a key part of the 'Best Man' film. It felt right [to include] some 20-something years later if we're revisiting and bringing this group and stories forward for a series," coshowrunner Dayna Lynne North tells POPSUGAR. "It's a way to connect the past to the present because, for me, this is not a reboot, it's a 'Where are they now?' kind of thing. So 'Unfinished Business' and Harper, still a source of mess. The more things change, the more they stay the same."

Fans have been waiting for Peacock's highly anticipated series ever since it was first announced in February 2021. Lee, the creator of the Best Man franchise, notes that the final instalment was originally supposed to be a third and fourth film but thought a limited series was much better suited for what audiences have been "clamoring" for.

"They really feel an affinity to them, so I love that people still want to see them and I still have something to say about these characters," Lee says. "That's rare. I think [viewers] are going to appreciate this time, especially around the holidays, to spend time with old friends that they met back in 1999. It's an opportunity to embrace them, see a reflection of themselves, and have some great nostalgia flowing."

THE BEST MAN, from left: Morris Chestnut, Harold Perrineau, Terrence Howard, Taye Diggs, 1999. ph: David Lee / Universal /Courtesy Everett Collection
Everett Collection

The "Best Man" cast credit Lee's genius writing as the reason their franchise has lasted so long. "It started on the page," De Sousa remarks. "He wrote a great script for the first movie, he wrote great characters, and he picked the right actors. It's literally one of those things that you can't explain. It was magic. We wouldn't have known from day one that it would've lasted all of these years."

Hall adds, "I think people really got invested in those characters and they've grown up with us, so they've watched us go through things that they've gone through. The good thing about the franchise is that it's had enough time between each reincarnation for people to experience them at different stages in their lives."

"We wouldn't have known from day one that it would've lasted all of these years."

The fervour of "The Best Man" has largely remained in fans' hearts because every member of the cast has been booked and busy since 1999. "One of the things that have helped sustain the interest is when you look at the cast from the very first 'Best Man,' we've all continued to go on and do so many other things," Chestnut explains. "Our fan bases from the other things have continued to grow, so when we came together for the second [movie], it brought all the fans back. They've seen all the films throughout the years, so not only have they followed us in the movies, they've followed our careers on different paths, [too]."

All these years later, the cast find comfort in knowing their franchise is iconic enough to last another 20-plus years for the next generation to enjoy. Looking back at "The Best Man," some of them still laugh at their favourite scenes from the film. "My favourite one is my first Shelby scene where you're introduced to the character," De Sousa shares. "Because I remember at the premiere, that scene, the audience burst into applause after my first scene: 'I'm watching you, Harper.' I can't ever repeat that, I don't know how that happened — some of it was improv on my part — but it's one of my favourite moments of my career."

Meanwhile, Chestnut, Long, and Hall note that the latter may have had the best scene of them all. "We talked about the stripper scene with Candace," Chestnut quips with a laugh, while Long adds, "That was a long night. I was so proud of Regina. I always think of her and how this was one of her first roles and she came in and just owned that strip scene and I was in awe of her like, 'Holy sh*t. I don't know if I could do that.'"

There are plenty more beloved scenes the Best Man franchise has gifted us over the years — from all the guys lip-syncing New Edition's "Can You Stand the Rain?" in "The Best Man Holiday" and Lance's smooth and sexy entrance in the first movie to Jordan's iconic "I don't want to hear about no godd*mn peas" line (and her slap for Harper heard around the world). Now, the hope is that "The Best Man: The Final Chapters," now streaming on Peacock, will offer fans more warm memories.

Ahead, take a nostalgic look back at "The Best Man" cast's careers and where they are today.

01
Taye Diggs Then
Getty | Ron Galella

Taye Diggs Then

Diggs was in the early stages of his acting career when he was cast in "The Best Man." At the time, he had only starred in notable films like "How Stella Got Her Groove Back" with Angela Bassett and "The Wood" alongside Omar Epps and Richard T. Jones. However, he bolstered his reputation in the rom-com realm when he took on the role of Harper Stewart, bestselling author of "Unfinished Business" and certified troublemaker who nearly derailed his college best friend's wedding on account of a one-night stand with his bride.

02
Nia Long Then
Getty | New York Daily News Archive

Nia Long Then

The '90s It girl was dazzling audiences long before she stepped into Jordan Armstrong's pumps. Before "The Best Man," Long had standout roles alongside major stars in "The Fresh Prince of Bel-Air" with Will Smith, "Love Jones" with Larenz Tate, "Boyz n the Hood" with her costar Chestnut, in addition to starring in cult classics like "Friday," "Soul Food," and "In Too Deep." But Long's role in Lee's 1999 film certainly became one of her most celebrated characters, gifting us the infamous improv slap scene we still love to this day.

03
Morris Chestnut Then
Getty | Ron Galella, Ltd.

Morris Chestnut Then

Compared to some of his costars, Chestnut had a nice-size résumé before he graced the big screen as the smooth playboy/womanizer Lance Sullivan. His credits included stints on shows like "Out All Night" and "Living Single," a couple of TV movies, and 1994's "The Inkwell," which starred heavy hitters like Tate, Glynn Turman, Jada Pinkett Smith, and Joe Morton. However, Chestnut's biggest role at the time was, without a doubt, Ricky in "Boyz n the Hood."

04
Sanaa Lathan Then
Getty | David LEFRANC

Sanaa Lathan Then

Lathan got her start in Hollywood in the mid-'90s with small roles in sitcoms like "Family Matters," "Moesha," and "In the House." But just a few short years later, her career picked up when she starred in films like 1998's "Blade," "Life," "The Wood," and eventually "The Best Man" as Harper's chef girlfriend, Robin.

05
Terrence Howard Then
Getty | Steve Granitz

Terrence Howard Then

Howard's acting career began nearly a decade before "The Best Man," and before audiences got acquainted with his eccentric Quentin Spivey character, some may have first seen him in a few episodes of the classic soap opera "All My Children." He also famously portrayed Jackson 5 singer Jackie in the "The Jacksons: An American Dream" TV biopic. Howard's other '90s roles include brief guest appearances on "Living Single," "Family Matters," and "New York Undercover." He also starred in "Dead Presidents" with Tate and Chris Tucker and "The Players Club" with Calhoun, Jamie Foxx, and Lisa Raye McCoy.

06
Regina Hall Then
Getty | Frederick M. Brown

Regina Hall Then

The year was 1999 when Hall made her big-screen debut as Candy in "The Best Man" with her iconic strip scene at Lance's (Chestnut) bachelor party. In a recent interview with Essence, the 52-year-old actor revealed that she got pointers for her dance scene from an actual stripper. "She said 'Put something on and look in the mirror and dance until you turn yourself on,'" Hall shared. "You can't turn anyone on if you don't believe it."

07
Melissa De Sousa Then
Getty | Ron Galella

Melissa De Sousa Then

De Sousa's acting career began years before she made an impression in "The Best Man" as her stuck-up character, Shelby. Prior to the film, the actor made a ton of appearances on sitcoms like "Living Single," "Moesha," and "The Wayans Bros." and also starred in series like "ER" and "Valley of the Dolls."

08
Harold Perrineau Then
Getty | Scott Gries

Harold Perrineau Then

Before he was motormouth nerd Murch in "The Best Man," Perrineau famously starred as Mercutio in 1996's "Romeo + Juliet" alongside Leonardo DiCaprio. He'd also appeared on shows like "Law & Order," "ER," "Living Single," and "Fame" the series as a dancer.

09
Monica Calhoun Then
Getty | Ron Galella

Monica Calhoun Then

Calhoun was already a seasoned actor by the time she played the role of Lance's bride-to-be, (not-so) innocent Mia, in "The Best Man." Before the 1999 film, she starred in "Children of the Night," "The Jacksons: An American Dream," "Sister Act 2," and "The Players Club." She also had small roles on shows like "A Different World," "The Wayans Bros.," and "The Jamie Foxx Show."

10
Monica Calhoun Now
Getty | Frazer Harrison

Monica Calhoun Now

After adding "The Best Man" to her résumé, Calhoun went on to star in other films like "Love & Basketball," "Civil Brand," "Pandora's Box," and "The New Edition Story" TV miniseries. The 51-year-old also had roles on shows like "NYPD Blue," "Everybody Hates Chris," and "Diary of a Single Mom." Her most recent role was in a Lifetime thriller called "Safe Space," starring Nicole Ari Parker and Boris Kodjoe.