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

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.

Fast forward to today, Diggs has added a few more entries to his rom-com list, including "Brown Sugar" with his costar Lathan, "Baggage Claim," and "Set It Up." Not to mention wowing audiences with his performance as Benjamin in 2005's musical drama "Rent" and cracking up viewers in "Malibu's Most Wanted." In addition to reprising his role as Harper in the Best Man franchise, the 51-year-old actor has a slew of TV credits with stints on shows like "Private Practice," "Murder in the First," "Empire," and currently The CW's "All American" as Coach Billy Baker.

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.

Today, Long is still a booked and busy actor. In addition to "The Best Man: The Final Chapters," she's also starring in an upcoming thriller with Storm Reid called "Missing" and the Netflix rom-com "You People" alongside Eddie Murphy, Jonah Hill, and Lauren London. Some of Long's past notable credits include film franchises like "Big Momma's House" and "Are We There Yet?" and Netflix thriller "Fatal Affair," on which, for the first time in her career, she also served as an executive producer. Moreover, the 52-year-old has graced our screens in many a series such as "Third Watch," "Big Shots," "Dear White People," "Empire," and "NCIS: Los Angeles."

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."

Twenty-plus years after "The Best Man," Chestnut is still a Hollywood heartthrob with an even lengthier bio. The 53-year-old had a nice rom-com run in the early 2000s with movies like "The Brothers," "Two Can Play That Game," "Breakin' All the Rules," and "The Perfect Holiday." He also starred in basketball classic "Like Mike" with Bow Wow, "Ladder 49" with Joaquin Phoenix and John Travolta, and thrillers like "The Call," "The Perfect Guy," and "When the Bough Breaks." Most recently, Chestnut joined an ensemble cast for Fox's "Our Kind of People" and guest starred on season five of "All American" with his "The Best Man" costar Diggs.

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.

Shortly after Lathan starred in "The Best Man," she booked her next big role: Monica Wright in the classic drama "Love & Basketball." The career-defining role soon led the 51-year-old actor, who's also the daughter of big-time producer Stan Lathan, to other films like "Disappearing Acts" with Wesley Snipes, "Brown Sugar" with Diggs, "Out of Time" with Denzel Washington, and "A Raisin in the Sun" alongside Phylicia Rashad and Sean "Diddy" Combs. Most recently, the seasoned actor made her directorial debut with Paramount+'s "On the Come Up," which premiered at the 2022 Toronto International Film Festival.

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.

Since the late '90s, Howard has had an accomplished career with film credits like best-picture-Oscar-nominated film "Ray," "Biker Boyz," "Lackawanna Blues," "Idlewild," "Red Tails," "The Butler," and probably his most notable (and most quoted), "Hustle & Flow." The 53-year-old actor also enjoyed a successful six-season run on Fox's "Empire" as the infamous Lucious Lyon but recently told Entertainment Tonight he has plans to retire from acting altogether.

"This is the end for me," he told the outlet. ". . . I retired two years ago, for the most part. I was done . . . I asked Sidney Poitier 10 years ago does he want to do any more work, and he said, 'Why would I spend my last 10 years doing an impersonation of myself?' And that's what I've gotten to."

Howard expressed similar sentiments in a recent interview with POPSUGAR when speaking about the next generation of actors. "I'm hoping that the actors that come up behind us will make the stuff we did look like it was just fool's play," he said of the Best Man franchise. "You know, impress me. Create something better."

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."

Shortly after Hall's feature-film debut, she starred in "Love & Basketball" as the older sister of costar Lathan's character. She went on to star in other films like the Scary Movie spoof franchise as her iconic character Brenda, "Paid in Full," "Malibu's Most Wanted," the Think Like a Man franchise, "About Last Night," "Girls Trip," "Little," and most recently, "Honk For Jesus. Save Your Soul."

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."

After "The Best Man" premiered, De Sousa enjoyed stints on TV shows like "One on One," "Reed Between the Lines," "Single Ladies," "Shameless," "Black Lightning," and, most recently, "Our Kind of People." The 55-year-old also starred in a handful of movies, including "Miss Congeniality" and "Constellation."

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.

After starring in "The Best Man," Perrineau blazed an incredible trail in Hollywood, starring in everything from "Oz," "The Matrix Reloaded," and "Lost" to "Sons of Anarchy," "Criminal Minds," and Fox's "Star." Most recently, the 59-year-old actor played one of the leads of Epix's "From."

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."

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.