’90s Favorite “The Best Man” Returns with Holiday Sequel

“The Best Man Holiday” cast talks love, life and sequels with ORANGE Arts + Culture Assistant Editor Helen Fernandez.

By Helen Fernandez

The cast of “The Best Man” has reunited for a much-anticipated sequel. The best part? It’s just in time for the holidays.

On Nov. 15, “The Best Man Holiday” will hit theaters, along with the original cast members, such as Taye Diggs, Morris Chestnut, Nia Long, Regina Hall, Terrence Howard, Sanna Lathan, Harold Perrineau, Melissa De Sousa and Monica Calhoun.

It’s been 15 years since we last saw them in “The Best Man” in 1999. Things got a little crazy before the wedding when Harper’s (Taye Diggs) dirty laundry rose to the surface and all hell broke loose. The Best Man Holiday picks up where The Best Man left off a couple of years later. This time, the movie takes place around Christmas time and Lance (Morris Chestnut) has invited the gang over to his home for a reunion.

Some of the cast members took time out of their busy schedule to chat with ORANGE about what viewers can expect from this sequel.

Writer’s note: If you haven’t seen the “The Best Man,” no worries! The cast all seemed to agree on one thing, if you haven’t seen the first one you’ll still be able to enjoy the sequel.

ORANGE: How does this film differ from the typical movie sequels?

Sanaa Lathan: The characters are at different times in their lives. Some of them are completely different people than who they were in the first. And what you like about the first — all of the layers and the chemistry, the laughs, the drama — is incorporated into this, as well. But it’s a completely different take.

Taye Diggs: Right, you don’t have to have seen the first one to get the second one. And we’re hearing back from a lot of people that the fact that real time actually has passed is something that differs from a lot of sequels. I know that as an actor it was great to come back and see the group 15 years later as friends, but then also deal with the same group of actors that have matured 15 years as actors, as well. That was something we enjoyed.

Diggs and Lathan on the representations of African-Americans in Malcom Lee’s films: 

Diggs: We, as black people, we have come along way, since you know, 15 years ago. What was great about the first one was that there weren’t a lot of movies like “The Best Man,” unfortunately, because, you know, that’s just not where the industry was. We, as a black people, have come further and I think you can see that in the film.

Lathan: And still there’s a long way to go. I would like to see us in more films. More diverse films.

Diggs: I think that these characters are even more relatable than they were 15 years ago.

Both Lathan and Diggs on being able to portray their classic roles from “The Best Man” fifteen years later:

Diggs: I attribute it to our personal relationships.

Lathan: You can’t create chemistry. It’s either there, or it’s not. And it’s still there 15 years later. In fact, we had such fun doing the movie that I think they should have made a movie about making the movie. Y’all should have seen what was going on behind the scenes. I mean, I know that in between takes we were having too much fun.

Diggs: I think you can attribute, you know, how good the movie is and the chemistry that exists in the movie, to that.

Nia Long on playing Jordan and Eddie Cibrian on playing Brian, her boyfriend, in the film:

Long: This business is difficult. You have to take your time. You have to be motivated by the things that really move you artistically and stay true to yourself. And I think with that you have a career rather than just a moment where you seem to be famous and then five years later they just don’t even know your name.

Cibrian: Very well said Miss Nia Long.

Long: Haha, thank you Eddie.

Both Long and Cibrian on interracial relationships in the The Best Man Holiday: 

Long: I believe you should love who you want to love and be with whom you want to be with. I think that the fact that Brian’s character is not African American is probably 10 percent of what makes Jordan uncomfortable when she brings him to meet the group. And unfortunately there are those people that are just ignorant to the fact that black people and white people can fall in love and make babies and have families. And I think we just need to broaden our horizons. And just be open to the fact that it does happen and it can happen. And it doesn’t mean that you’re selling out or you’re turning your back to your own group. It just means that you happened to fall in love with — because I think when you fall in love with someone you’re not falling in love with who they are, you’re falling in love with their soul. And souls are colorless.

Cibrian: I don’t think anybody is pure bred.

Long: Right! Haha.

Cibrian: It’s not like a dog breed where you’re just trying to you know breed pure. Everyone’s mixed.

Long: Especially now.

Cibrian on how he felt coming into the group of actor’s and being the only new one in the cast: 

Long: He was so scared!

Cibrian: Yeah, Nia saw that the first day. I was very intimidated by everybody. When you come into an environment where people have worked together before, they have a certain comradery that they’ve built already. You are stepping into a new situation with uncertainty, but I’ve been working with a handful of the actors on this movie before and everyone made me feel welcome and it was fine.


Long on how her character’s gotten over her romantic feelings for Harper: 

Long: I mean, look who’s sitting next to me! How could she not [laughs]? You know what, when Jordan sees that Robin is pregnant, that kind of seals the deal for her. Like, okay, they’re married now, they have a child on the way, time to move on. But there’s still that unspoken tiny bit of tension between Jordan and Harper, but I don’t think it’s sexual tension anymore. I think it’s just that thing that happens when you could have been with someone, and it actually never happened and then you both move on and there’s this little tinge of ‘what would have happened?’ or ‘could it have happened?’ right?

Cibrian: Yeah, always. The what ifs?

Long: The what ifs. The what ifs are big.

Both Cibrian and Long on how the movie will be appealing to those who didn’t see the first one: 

Long: I don’t think you need to see the first one to enjoy the second one. I think it’s a fun thing to do, but I actually think you can see the second one and then go back and watch the first one. Or you can do it the other way around. And Malcom did something really cool, the big montage in the beginning of the film, which sort of catches the audience up to speed on what’s happened in the last fifteen years. So yeah, I think you can enjoy them together or separately.

Cibrian: Yeah, at the time I didn’t see the first film when I read the script. And when I read the script, I already knew, just by the way Malcom set up all the characters and the way they were interacting, you can tell what their relationships were. You can tell the kind of subtext within the scene just by the writing. So you know, it’s a standalone movie for sure, and like Nia said, it would be interesting if you haven’t seen the first film, to watch this one first and then go back and see everything that transpired beforehand. It’d be pretty fun to do.

Long on why Eddie’s character, Brian, is such a good match for Jordan: 

Long: It’s the dimples. I mean, have you seen the dimples? I know he’s heard this his entire life, but she literally dove into the dimples and fell in love.

Cibrian: It’s as simple as that.

Long: It’s that simple [laughs].

Cibrian: You don’t have to make it complicated guys [laughs].

Long: Right? It’s like come on! Take advantage of the obvious [laughs]. But on a more serious note, I do think that, you know, we work in the same world. We have a respect for understanding business. And our paths crossed. And we explored one another, right?

Cibrian: Yeah. There’s a strong connection that the audience will see that they have. And we’ve both come to realizations about our relationship. I think that we might stay together.

Long: I think we might have some babies.

Cibrian: You never know.

Long: Yeah, might get married. You never know.

Cibrian: We’ll practice a lot.

Long: For sure. Definitely. We’ve already made that real clear [laughs].

Long on how The Best Man Holiday is a realistic sequel: 

Long: Yeah, I think so, I think you’re catching up with these characters fifteen years later. Getting to see how they’ve grown. Your’e seeing the mistakes they’ve made. The process of life.

Long on her character Jordan’s biggest flaws: 

Long: She’s a perfectionist. She, you know, wants everything to be perfect. She probably over-thinks. She doesn’t trust as easily as she should.

Both Cibrian and Long on what they want viewers to take away from the film: 

Cibrian: For me, this whole movie, you really go through life experiences. Friendship, lost friendship, reconnection, dealing with loss, what’s important in life, love, there’s just so many things.

Long: Forgiveness. There’s so many themes. So many things, that when you leave you’re gonna go, “wow, I’m experiencing some of this in my own life.” And I think that’s what makes the film special. It really does mirror the journey of life from being fresh out of college, to starting your career, to being an adult, to getting married, to having children. And then some of the things that happen in life that may not always be so pleasant.

Long on how the relationships reflect the current culture: 

Long: I think if you watch this film you can find a little bit of yourself in one of the characters if not a couple of the characters put together. Malcom is great with character development. He really is able to give each character a very strong voice. And that’s a difficult thing to do.

Cibrian: These are all contemporary issues. There’s nothing old-fashioned about it. This all resonates with people today. You’re gonna find yourself in one of these characters. You might have not dealt with it the same way these characters have dealt with it, but you can definitely relate.

Long on how her character has evolved: 

Long: Jordan is a lot more vulnerable and open to love and now that she’s sort of gotten her career in order and she’s where she wants to be career wise, I think she’s realizing there’s more to life. And when the whole group gets together over the Christmas holidays, she sees how a lot of her friends have moved on, they’ve had children, they’ve gotten married, and life continues to grow and move. And she’s sort of been on this one-way street to success and she gets that, but then realizes ‘oh which way do I go now?’ And once she connects with Brian, I think she realizes that there’s a lot of power and importance and beauty in falling in love. And she kind of allows it to happen. She’s grown up.

Didn’t catch “The Best Man” in 1999? Watch this trailer:

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