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The Best Man’s Last Hoorah: An Inside Look Into The Cast’s Grand Finale

The ensemble cast and franchise creator, Malcolm D. Lee, take a stroll down memory lane to say goodbye.

When The Best Man first came into our hearts and movie screens in October 1999, it instantly became a regarded classic within the culture—a goal creator Malcolm D. Lee knew he’d achieve when he wrote the script. Between the ensemble cast—Morris Chestnut, Taye Diggs, Nia Long, Harold Perrineau, Terrence Howard, Monica Calhoun, Sanaa Lathan, Regina Hall, and Melissa De Sousa—who showed the real, Black, successful, multifaceted human experience in a comical albeit messy way, the franchise only matured with time leading to the blockbuster film success 14 years later with The Best Man Holiday and now its culmination—almost 10 years after that sequel—with The Best Man: The Final Chapters.

We grew to love, hate, defend, and admire the philandering athletic playboy Lance Sullivan (Chestnut), problematic drama magnet Harper Stewart (Diggs), overachieving commitment-phobe Jordan Armstrong (Long), lovably meek and indiscreet Julian Murch (Perrineau), imperfectly angelic Mia Sullivan (Calhoun), soul-seeking loverboy Quentin Spivey (Howard), fiery avoidant force-of-nature Shelby Taylor (De Sousa), fluid advocate Robin (Lathan), and the sexy intelligent student of the world Candace (Hall).

Greg Noire/VIBE

As The Best Man cast and crew say goodbye to their characters, stories, adventures, and fans, their sentiments are reflective about their final round. Lee remembers being close to quitting the business when he finished the script for the first film—“I came upstairs and I said, ‘If this ain’t the script that they want, I don’t know what they want. I’m going to not pursue filmmaking.” Fast forward 23 years, and he’s grateful to have been able to pour so much into its subsequent sequel-turned-series to end things his way.

“I felt like it was a story that was universal, that everyone would be able to relate to, had cultural specificity, and it was going to feed an audience that was really hungry for it,” recalls the Queens, New York native, while talking over Zoom. What he wasn’t expecting, though, was for it to grow into a franchise. “But just so happens that it was the right story to tell with The Best Man Holiday and I really wanted to give the characters something more adult to deal with. With The Final Chapters, it’s even more adulting that is going on—everything that happens when you are in the sandwich years with taking care of your parents, taking care of your kids. You are reevaluating your life and who you are, who you’re going to spend the rest of your time with. It’s a lot that goes on at this stage of our life, and I wanted to just display that.”

When the gang returned for Holiday, audiences admired how they embodied the fountain of youth and how, yet again, this story emotes a different type of pain as we had the tragic deterioration of Calhoun’s character—a central force and guiding light among these friends. It caused each person to grow up for different reasons. Jordan needed to open herself to love. Robin needed to stop seeing Jordan as her enemy. Shelby needed to stop pining after Julian while he needed to learn how to communicate effectively with his wife. Harper and Lance needed to address their passive indifference, which couldn’t have happened without Lance and Mia coming to terms with their unfinished business.

The Best Man: The Final Chapters comes in a new package as an eight-part episodic series through NBC’s Peacock streaming platform. However, the themes are familiar enough to touch on the layered complexities associated with grief, mental health, newfound love, raising your parents and teenagers, and outgrown relationships, which all fall under the “midlife metamorphosis” umbrella. That term was coined by co-showrunner Dayna Lynne North.

“The biggest thing was that midlife does not have to mean crisis. That’s, for me, what was so important,” the acclaimed writer-producer explains. “For some characters, it’s a renaissance and I think we kind of keep going through rebirth and renaissance, if we’re lucky, throughout our lives.”

Throughout the limited series, there will be a time for joy, anger, relief, angst, surprise, fear, and of course, laughter. It is a ride, so prepare accordingly.

Each character was tailored for the cast (as told on Zoom) as individuals and now lives within them. The actors were granted the license to express us in an authentically relatable way, which is how they gained such a steadfast fanbase.

“These are people you want to talk to, you want to hang out with or maybe even emulate,” Perrineau says with passion. His onscreen partner, Hall, added that the franchise “showed the humanity and complexity of relationships between friends.” Particularly, with where her relationship with De Sousa’s character lands by the end, the comedic actress states, “I think it’s the potential of where adult friendship can go. I mean, Shelby’s a rooted part of this group of friends and I think what’s honest about it. They didn’t get here easily. But when you love a group of people, you have to set aside a personal grievance and be bigger. I think there’s a real honesty and truthfulness to that.”

For their respective romantic relationships, they each experience an awakening whether it brings them closer together, drifts them further apart, or seeks out an entirely new beginning. Howard jokes, “Well, I believe that Quentin has now realized that he had more in common with Murch than he ever thought he would. Oh my God…”

To tag on to character detail, Diggs expresses, “My character has gotten even more in his head than he was in the past. And even in success is questioning who he is and what he really wants and what he should be striving for.” Coincidentally, Harper finds himself successful professionally—a trait he shares with his twin flame Jordan—but both actors admit that, in life, your soulmate doesn’t have to also be your romantic partner.

“Well, it’s definitely not as cut and dry as [you think]. I think there are levels and it’s about a connection,” Diggs explains.

A similar relationship that chose to accept their lovers-and-friends fate was Quentin (Howard) and Shelby (De Sousa)—spoiler alert! After years of ignoring the obvious and nearly losing each other forever, they both stop fighting the true desires of their hearts. On Shelby, De Sousa admitted, “She is a full woman with a full range of emotions who’s coming to face what life is really about and then has to adjust.” Howard calmly chimes in, “There’s a simplicity in complexity, because you know at the end it all comes together. But you will trip and stumble over yourself in trying to navigate and control the complexity.” Having a career that spans many memorable scenes and characters, Howard’s breakdown shows he understands his roles from a bird’s eye view and ground level.

Sanaa Lathan, Nia Long, Regina Hall, Melissa De Sousa dressed in black and gray evening attire on red carpet
“The Best Man: The Final Chapters Premiere Event” (L-R): Sanaa Lathan, Nia Long, Regina Hall, Melissa De Sousa at the Hollywood Athletic Club on December 7, 2022. Arnold Turner/Peacock

“The best thing to do is to be patient and walk your way to the other end of it. And that’s what you as an audience member get to watch,” he continues. “And you can see the stumbling blocks that may trip someone else, and you can turn them into stepping stones for the next person by how you deal with it. So that’s something that we gained in these three interactions that we’ve had to show our world.”

What The Best Man franchise has done for Black cinema was change the game. Chestnut extends that sentiment: “I think there have been a lot of different films and projects that try to recreate that same type of tone and image.” Diggs jumps in and boldly adds, “There would be no Black cinema without The Best Man.”

The indelible mark they’re leaving behind goes beyond the cast. We’d be remiss if we didn’t highlight the cultural focal points like Cameo’s “Candy” being paired with the Electric Slide dance, the men performing AirBand with New Edition’s “Can You Stand The Rain,” Stevie Wonder’s “As” being the record for both mourning and moaning, or the genius of D’Angelo’s “S**t, Damn, Motherfu**er” serving as the soundtrack to Lance uncovering Mia’s infidelity.

“This cast and Malcolm [D.] Lee in particular, have given audiences, especially in the African-American community a chance to experience our culture in ways that weren’t previously available,” adds Perrineau.

As you’ll see with Final Chapters, old dogs can learn new tricks. Everyone was allowed to bloom and branch out in the ways they needed to, whether it was apparent to them or not. “I think The Best Man showed that Black people are not a monolith and that we can show up on screen in many different ways and still be profitable, still be enjoyable,” he points out. “That’s one of the legacies I think The Best Man leaves.”

Their found family—whom Lee affectionately calls “The Black Pack”—and friendship, furthermore, is definitely one that cannot be duplicated. During card and billiard games, intimate poolside chats, and even within screaming matches, they play hard, occasionally fight dirty, but love harder.

“What will stick with me most is the amount of love, artistry and fun that this group of human beings bring,” reflects Perrineau on their unique, collective relationship. “They are the best group of people on- or off-screen, and I love getting to play with them. Because that’s what we do on screen, we play, and that’s dope AF.”

Their foundation is rooted in unwavering love.

“The Best Man: The Final Chapters Premiere Event” (l-r): Morris Chestnut, Terrence Howard, Malcolm D. Lee, Taye Diggs, Harold Perrineau at the Hollywood Athletic Club on December 7, 2022 Photo by: Arnold Turner/Peacock

Like their Final Chapters, the cast is asked to give their goodbyes to their characters. Their answers varied between playful suggestions and earnest farewells. Long tells Jordan to “live a little. Go get on a strip pole. Have some fun.” Hall reminds Candy, “You know, you did good. Life turned out well.” To which Chestnut adds, “I think all the characters, I mean to a certain degree, throughout all of our challenges and everything that we’ve gone in personally and professionally, I think they’ve all done well.” De Sousa urges Shelby to “trust in love and trust in yourself.” While Howard shares, “continue to live. And if not, I’ll see you in the next life.” 

The greatest takeaway is that everyone involved is proud of what they’ve done. North equates the road to this project this way: “The journey is going to be so fun and so satisfying and surprising, but get ready.” As for Lee, he finished what he started. “There’s nothing else to tell,” he states.

Final Chapters may be a wrap on these stories—a “fitting tribute” as described by the leader of this moment—which is still hard to grasp. However, to the cast, crew, and fans, Lee bows out with these words: “It’s been a great ride. Hope you enjoyed.”