When filming for The Best Man began in New York City on October 5, 1998, the members of the ensemble cast were in various stages of their careers. While Sanaa Lathan, Regina Hall, Melissa De Sousa and Monica Calhoun were in the early days of establishing themselves as household names, Nia Long, Taye Diggs, Morris Chestnut, Terrence Howard, and Harold Perrineau were just entering their prime as movie stars. 

“I was so excited to meet Nia Long,” says Hall, who made her feature debut as Candace, aka Candy, in the 1999 film. “I was like, ‘Nia Long, I love Nia Long.’” 

Having already appeared in Boyz n the Hood with Chestnut, as well as Friday, Love Jones, and Soul Food, Long was like a “big sister” on set, recalls Lathan, who, prior to The Best Man, had worked with Diggs on The Wood and would go on to be his co-star again in the 2002 rom-com Brown Sugar. She and Hall, however, who had yet to cross paths in the industry, had what the Black Monday star jokingly calls “pre-meet beef.” 

“There was a dress I wanted to wear, and they were like, ‘Oh, you can’t wear that, Sanaa’s wearing it.’ And then someone says, ‘She’s going to look so beautiful in it.’ And I was like, ‘Who’s Sanaa that I can’t wear this dress?’” Hall recalls. 

“I didn’t like you before I met you either because my cousin auditioned for Candy and I wanted her to get it,” says Lathan. “I was so mad, and then I remember you walked in the trailer, and I was like, ‘Oh, she looks like my family.’” 

“And I saw you and I was like, ‘Okay. Alright. Okay. I get it. She’s beautiful,’” Hall adds. 

The playful banter between the actresses during the shoot for their Of The ESSENCE digital cover illustrates an earlier declaration from Howard, who’d garnered acclaim for his roles in Dead Presidents and Mr. Holland’s Opus by the time the Malcolm D. Lee–written and directed project came around. Speaking to the relationship, the cast has built with one another off-screen, Howard says: “Out of the 25 years that we’ve all been together, not one of us have ever had an argument where we’ve raised our voice to each other.” 

That the cast of The Best Man has maintained an unwavering affinity not only for one another but also the characters they reprised for 2013’s The Best Man Holiday and the forthcoming series, The Best Man: The Final Chapters, is a testament to their awareness of the unique position they hold in Hollywood.  

“I feel like it’s never easy and we’re naturally in a situation to have to be competitive but that doesn’t mean we can’t love and respect one another,” says Long, who plays Jordan Armstrong in the franchise. “It also doesn’t mean that we can’t share what we know because here’s what we do know: this shit goes like this, it goes like this, it goes like this, it goes like this and then it goes right back up,” she says, motioning different directions with her hands. “So, the best thing we can do is at least be consistent with each other because we know that this industry is not consistent at all.” 

During the late nineties’ era of The Best Man, one constant within Hollywood was the idea that there could only be one when it came to Black talent. For Chestnut, who was cast as the once-promiscuous, religious pro-footballer Lance Sullivan in the romantic comedy, that one was a particular type of role for a Black actor. 

“I was auditioning for gangster number one, gangster number two,” he recalls. “It was a gang genre at the time and, of course, I wasn’t getting them. It was just so refreshing to see us all as young, successful Black people on-screen.” 

For Howard, the battle was the pervasive opinion that there could only be one leading Black male. “Head cutting” is how he describes the practice of singling out the “it” Black actor of the time for lead roles, and it’s one he expected to be implored when he read with Diggs during his audition. 

“[Taye] had been offered the lead on The Wood and I had been trying to talk to the damn director. They wouldn’t see me, neither would the casting director. So, when I see him [at the audition], it’s like, wow, the head cutting has to begin. And that’s what I think makes this so great because as much as we became friends, we were always aware that only one person is going to take the frame.” 

Howard, with his biting one-liners and cunning observations as the recalcitrant Quentin Spivey, was often that person. Shelby, played by De Sousa, has been his audacious female counterpart throughout the franchise. 

“Malcolm wrote me the best entrance scene, I think, in cinema,” she recalls of the moment she walks into a bar and finds her then-boyfriend Murch, played by Perrineau, reunited with his college friends. “Well, well, well, the gang’s all here, back in effect,” she remarks disapprovingly. “Break out the 40s.” 

“I remember at the premiere we were at the Mann’s Chinese and everyone was watching and after my scene the audience applauded,” says De Sousa. “That was a great moment for me. Every movie after that I was like, ‘Malcolm, what’s going to be my opening? How am I going to come in?’ I wanted that to be my thing.” 

When pre-production began on The Best Man Holiday in November of 2011, the cast reunited with all of the accolades and real-world experiences befitting established thespians. Howard was now an Academy Award–nominated actor following his lead role as the drug-dealing Memphis pimp DJ in 2005’s Hustle & Flow. Long had just given birth to her second son months before filming commenced. And much like Harper, who found himself in a vulnerable state in the long-awaited sequel, struggling to hold his marriage, finances and career together after his success peaked upon the release of his debut novel Unfinished Business, Diggs was quietly working through struggles of his own. 

“I was going through some really heavy duty, personal stuff and I had to get emotional,” he says of the scene in the film when his character admits to Q that he needs to borrow money. “Right before—this is where I knew you always had my back”—he tells Howard, “I said, ‘Listen man, right before we start the scene, just say this word to me.’ And I gave him a word. And immediately, he didn’t know what I was talking about, but he was like, ‘I got you, man.’” 

“So, we start the scene and he locked in with me. He looked at me and he said the word. Immediately I got emotional,” Diggs shares. “I remember that moment where we were all a team holding each other up, supporting each other.”  

It’s memories like that which make it hard for Diggs to accept The Final Chapters will indeed be just that when the series premieres on Peacock December 22. Picking up just years after the passing of Lance’s wife Mia, formerly played by Calhoun, over the course of eight episodes, the lifelong friends will continue to navigate unexpected changes and celebrate new beginnings. 

“I’m not convinced it’s over, personally,” Diggs admits. “I’m not approaching it like that. Depending on how well this does, who knows what’s going to happen.” 

It makes sense that the All American star would have such reservations. Fourteen years had passed between the first film and it’s Christmas-themed sequel which was a commercial success at the box office, grossing $71 million worldwide against a $17 million budget. Gathering the A-list actors together again another nine years later just to bring their story to an end doesn’t quite feel fitting. 

“I just hate goodbyes,” Diggs adds. “This franchise has meant so much to me and my life and my career. You guys were my first Hollywood friends and this movie really set the bar. So to have it come to an end and not have the possibility of us hanging out again, that’s daunting.” 

That prospect is equally unnerving for Howard. “It frightens me,” he admits. “They must know that maybe all life is about to come to an end on this planet for them to keep saying ‘the final chapters.’” 

He adds, “Everything is an omen. So, I say, okay, if this is the last day, man, it’s been great to hang with you all. I love spending this last day with you.” 

**

Photographed & Directed by Joshua Kissi
Styled by Bryon Javar
Director of Photography – Blake Myer @blakegmyers

Melissa De Sousa

Makeup: Tay Rivera – @tayriverabeauty
Hair: Randy Stodghill using Oribe at Opus Beauty – @hairjunkierandy

Morris Chestnut

Groomer: Gina Lopez using MAC
Cosmetics and Ben Nye – @geelow

Nia Long

Makeup:
Paul Blanch using Danessa Myricks at The Wall Group – @paulyblanch
Hair: Shaylin Jones at Crosby Carter Management – @shaylinjoneshair

Regina Hall
Makeup: Lewina David using Marie EyeLashes at Cloutier Remix – @lewinadavid

Regina Hall

Hair: Shornell Mcneal Young using Oribe at Crosby Carter

MGMT – @saishabeecham

Sanaa Lathan

Makeup: Saisha Beecham using Koh Gen Do Beauty and Sisley Skin Care at
Artists Management Co. – @saishabeecham
Hair: Kim Kimble using Kim Kimble Products at A-Frame Agency – @kimblehaircare

Taye Diggs

Groomer: Schuron Womack at Crosby Carter

MGMT – @iamschuron

Terrence Howard

Groomer: Gina Lopez using MAC Cosmetics and Ben Nye – @geelowSet Design:
Lauren Ivy – @lauren_ivy_one_hundred

Set Design: Lauren Ivy – @lauren_ivy_one_hundred

Set Dresser: Danielle Merendino 

Carpenter: Lee O. Roman 

 1st Assistant: Clark Wacunza  

2nd Assistant: Jesse Belvin  

Photo DigiTech: Sean Kiel  

Key Grip: Bevis Tran  

1st A/C: Billy Brigs 

2nd A/C: Robbie Alpine 

Steadicam + Jib: Kevin Lachman  

Gaffer: Robert Julin 

Video DigiTech: Lanlin Wong 

Best Boy Electric: Bailey Clark 

Electric: Maile Edwards 

Best Boy Grip: Daniel Kang 

Grip: Kane Katubig 

Sound Tech: JP Robelo 

 Styling Assistants: Kimberly Batino, Brandon Washington, Louis Johnson IV  

Hair Assistant: Lena Jaye 

Tailors: Marc Littlejohn, Da Shone Gray  

Production Managers: Perris Cavalier, Eve Van Dyke 

Production Coordinators: Diedre Ehule, Alaura Wong 

Production Assistant: Frankie Benkovic 

Photography Direction by Michael Quinn – @_mq______

Production by The Morrison Group – @themorrisongroup

With Thanks to Heirloom LA – @lermitagebh

Shot at Smashbox Studios – @smashboxstudios