The Best Man Holiday: Director Dishes Getting the Gang Back Together

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The Best Man Holiday director Malcolm D. Lee met us for a chat recently where he talked about getting the “band” back together for the sequel that is 14 years in the making. Before even approaching the studio about making a sequel to The Best Man, Lee gathered the cast for a get together to let them know he had ideas for a second film and to see if they would be game.

The Best Man Holiday Taye Diggs

“I said, ‘Let’s all get in the same room. I have an idea for a sequel, and if you like it, great. We’ll pursue it. If you don’t, we’ve at least all seen each other again and we’ve all been in the same room together.’ It was a great dinner and it was lots of fun and drinks flowing and food eaten and a very high bill that I was paying for,” Lee said and laughed.

“But I was glad to do it because they liked my idea.”

Next up, he approached the powers that be, armed with a cast ready to update these characters audiences first fell in love with in 1999. “I pitched it to the studio and they liked the idea,” he said.

Lee penned a script, and they initially had reservations about what they were reading. Not sure if this is spoiler, but just in case… spoiler alert: someone dies.

“They were like, ‘Oh, this is kind of dark. Do we really think there should be a death? Do we really think that she should die?’ And I’m like, ‘Yes!’ And they were like, ‘Well, what if we were to do a destination wedding?’ I’m not lying to you!”

He promptly told the studio that the script and story that was pitched to the cast and subsequently pitched to the studio is what it would be, no ifs, ands or buts. “I was like, ‘Guys, I don’t want to do that. this is what I want to do. This is what my cast wants to do. Before we entertain any other ideas, let my cast do a reading for you and let’s see where we go,’” Lee recalled.

Then he brought in his cast: Morris Chestnut, Nia Long, Monica Calhoun, Melissa De Sousa, Taye Diggs, Regina Hall, Terrence Howard, Sanaa Lathan, Harold Perrineau… and they read for the execs.   

The Best Man Holiday Terrence Howard

“We had the reading and they were sold. They were like, ‘Okay. We get it. We understand.’ When they were seeing the dailies, they were like, ‘Oh my God! This is amazing.’”

He was surprised that given the success, that has grown exponentially, for the first film that it was even a question over the direction he wanted to take his characters. “People loved the first movie for the reasons I’ve stated before. The reason they were nervous was because it was such a departure from the first one. And I said, ‘Yes, in a way, it is. But it’s still fun. It’s still funny. The characters are still engaging. But we have literally some life and death issues here, and that’s what we’re going to deal with,’” Lee said.

It is kind of like life itself. This is what people would go through over a 14 year period, so why wouldn’t Lee’s film reflect that? “Let’s continue to grow. Let’s not do the same thing. We’re coming back together. Let’s do it and let’s do it really well,” Lee admitted.

“So, in terms of the whole sequel business, it was a departure, but one that was faithful to who these characters were. And people love these characters, and whatever situation we put them in, I think people will be engaged by them.”

Now that he has had 14 years to reflect, Movie Fanatic wondered what he thought it was about this group of characters whose resonance has only deepened with time. Lee compared it to a group of 1980s actors, and a certain film of that era as well.

“In the eighties, there was the Brat Pack, and this is the Black Pack. This is a collection of really talented actors who embodied their role so thoroughly in the first movie. It was a movie that spoke to a generation of African American people who were educated, who were sophisticated, who were going to college, had had experiences, and didn’t define themselves as strictly black,” Lee said.

“The first movie was inspired by The Big Chill and that was a reunion of college friends. It’s funny. Even watching that movie when I was very young, I guess 13 or 14 when that movie first came out, I didn’t quite understand. Every time I saw that movie, it revealed something new to me about the characters and what they were going through. I didn’t even focus on the fact that it was a funeral that they were coming together for.”

The audience for the first film, Lee felt, “had the specificity of being African American, but they were just doing everyday American things and having American ideals. So I think that was refreshing for audiences who hadn’t seen themselves like that on the big screen. It’s very gratifying because that’s what I intended to do. I intended to make a movie that would be regarded as a classic.”

The Best Man Holiday Morris Chestnut

He also did not want to do a sequel right away. “I didn’t want to be pigeon-holed as an artist. I wanted to be able to have other stories to tell. I wanted to live some life, and I wanted these characters to live some life,” Lee said. “I thought there might be an audience that was ready to see these characters again, maybe 10 or 12 years later, and tackle some new territory.”

Lee is also quite proud that the film teased in The Best Man Holiday trailer is closing out a fantastic year for African American movies, with The Butler, Fruitvale Station and 12 Years a Slave all finding diverse audiences and box office success. But, Lee also cautions that he’s seen this type of attention before, and hopes this trend is actually more of a way of doing things in Hollywood.

“We’ve seen these kinds of things before, but it’s different this time. When Spike came out with his movies, it was like everyone was coming out to a Spike Lee movie. Then it was John Singleton making Boyz in the Hood and all these hood movies that followed. And then, there was Waiting to Exhale, Love Jones and The Best Man and a slew of black romantic comedies. And then, there were a couple that just didn’t work and they said, ‘We’re not making these movies anymore,’” Lee said.

“Now, here’s opportunity. What’s great about this is there is a greater diversity of product. I mean, from 42 to Fruitvale to 12 Years a Slave to The Butler, Baggage Claim, and Black Nativity coming out, there’s just a slew of choices out there for African American audiences. It’s for audiences. This should be the norm. We should just keep going with the quality and the diversity of work. We should have choices like everyone has at the movies.”

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The Best Man Holiday Quotes

Harper: Brian McDaniels... I like to ski in Vermont. I like to date chocolate girls.
Jordan: Shut up, Harper.

Candace: I'm just saying, Jordan's good people, you should get to know her.
Robyn: What's to know? She's career-obsessed and lives on her BlackBerry.
Candace: True, but she's not some ideal from a piece of fiction. Now, her man, on the other hand, is iconic. Mmm. If I went that way, that's what I'd get. A tall, vanilla swagger latte. I like, I like, I like.

The Best Man Holiday Review

The Best Man was a surprise hit when it came out in 1999. It shot right to the top of the box office charts. So, what’s really a...

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The Best Man Holiday Trailer

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