From A Striptease To A Lifelong Friendship: Regina Hall And Morris Chestnut Look Back On Their Projects Together

Regina Hall and Morris Chestnut met on the set of the 1999 classic The Best Man and have remained close friends to this day. Both Morris and Regina went on to build impressive résumés for themselves, filled with unforgettable movies and bingeworthy series, but there's something about seeing these two together onscreen that we can't get enough of.

So last month, I sat down with Regina and Morris to reflect on the sets they've shared, behind-the-scenes laughs on The Best Man: The Final Chapters, and what they've learned about each other along the way.

THEN: When was the first time you two actually met, and what were your first impressions?

Morris Chestnut: Let me go first.

Regina Hall: We met at the same time [laughs]!

MC: It was on a set of this movie called The Best Man. We were doing a scene — it was a bachelor party scene — and someone comes in and they don't have any clothes. Her body's all fine and everything, and it was Regina [laughs]!

RH: And I was like, "Oh shit, it's Morris Chestnut!" I was very excited. My friends were very excited. They had a million questions.

MC: We were at a bachelor party scene, and all the guys were very excited for Regina. That was the first time we met.

NOW: After getting to know each other more and working together on multiple projects, how has your opinion changed about them? And what surprised you the most about them?

RH: Morris was and is fine, right? But I think when a guy is really handsome and is aware of it, then it's not handsome. Morris isn't aware of it. He doesn't think about it. It's not a part of how he presents himself. So that was probably the nicest — not that I would have thought about it at that age. I was like, "Ooooh!" But I think him being really kind, really inviting, and warm.

MC: In terms of Regina, the Candy role was very impactful, but it was really just a sliver of what she could do as an actress. To see her career evolve and see just the range of things that she's done throughout the years, it's been very, very impressive!

THEN: Regina, The Best Man was actually your first feature film. Was there any initial hesitation when you first considered taking on the role because of the striptease scene? If so, what made you ultimately decide that that was the right move for your career?

RH: Yeah. No! I mean, if I got it, I was gonna do it. With the dancing, I was more so thinking, Was I going to be able to pull that off? Was I going to be able to pull off that she's supposed to be enticing to the men? You wonder, are you going to be attractive enough? You know what I mean?

Also, being surrounded by such an incredible cast of women. You have so many beautiful women who are in the cast as well, so I think it was just, like, being new and fitting in. There was nervousness, but the excitement was just as big!

My brothers seeing it...I think I also thought about my brothers seeing it. My father passed away, but I remember I was like, What are my brothers gonna feel?

MC: And what did they say?

RH: They were like, "Gina, you had your ass out?" I mean, it was a big deal for my brothers.

MC: Yes, she did [laughs]. Yes. She. Did.

RH: It was a big deal for my brothers, but yeah, that was a thought that I had.

NOW: Well, you left a lasting impression on fans, and your character was ultimately bumped up to the main cast. How do you feel about your character’s trajectory throughout The Best Man franchise, including The Final Chapters?

RH: Well, I think we've all been happy. I think one of the things director Malcolm D. Lee has done well is servicing everybody, without doubt, but still keeping true to what the story is about. I feel blessed that I was asked back the second and third time, so I have no complaints.

THEN: Speaking of the second time, the cast got together again for the 2013 sequel The Best Man Holiday. What was your favorite behind-the-scenes moment from that film?

MC: We just had a really good time! I think that...

RH: ...you learning the dance?

MC: [laughs] That was fun! I was just nervous learning that dance, because you know Harold Perrineau is an incredible dancer, and Taye Diggs can really dance — me, not so much...and Terrence Howard, not so much [laughs]. So I was like, "Listen, man, when we gonna get together and do?" Terrence would always miss rehearsal; that's why, when you actually see the movie, he's kind of improvising and doing some Michael Jackson stuff.

RH: But with full confidence he was doing the dance [laughs].

MC: With full confidence [laughs]! You know T-Howard!

RH: It was fun doing the fight scene. It was fun with Melissa De Sousa, especially because we were all together. So the whole house was waking up seeing the craziness of the fight!

MC: Yeah, you guys really went for it. They went for it!

RH: [laughs] We really did!

NOW: When you first heard that Peacock was interested in creating a series instead of a film to close out the franchise, what were your thoughts?

MC: I think it was a lot of intrigue because it's a different platform. We had read a script that was in feature film–length version, but then we were like, "Okay, it could be kind of interesting exploring eight episodes instead of just a two-hour movie." It's basically eight hours of our characters, so it was intriguing.

Was there any behind-the-scenes talk about making that decision? Like, did you all get together beforehand or discuss it via text?

MC: There was behind the scenes, but it wasn't about sticking with the movie. I think once we heard it was going to be on Peacock, we were open to it.

RH: Yeah, I think it was more just collective time frame, and we were just committing to do it together. It wasn't about like, "Well, I'm not sure about this if it's going to be a limited series." I think we were like, "Oh, okay. Let's see if we can find four and a half months."

MC: Yes.

RH: The window of time was really the issue.

THEN: Morris, fans were shocked by the plotline of The Best Man Holiday after eventually learning that we’d be saying goodbye to Monica Calhoun’s character, Mia. Your tears brought me to tears. What was the most challenging and rewarding part for you about making the sequel?

MC: There were two particular moments with the tears. The first one was at the casket, and Malcolm says, "Okay, when you're there, you're not breaking, but when the casket starts to go down, that's when you start to cry and break down." I said, "Okay." So those days are always tough, because the cast is all there and they're over there having fun and laughing, while I'm over here by myself with my earphones on and everything. On the first take, the casket didn't go down. He said, "Action," and it didn't go down. I was just waiting, holding it in, and waiting. And then I wasn't crying, so he goes, "Cut, cut. Morris, what are you doing?"

Another part of that was when I returned home, and we're crying in the bed; that was a lot. I don't know why we did that scene so many times. So at some point, I was just dry. I would just go into the closet, and I was waiting and just listening in the closet. I was just trying to get to a place that I was just emotionally fatigued, but it worked out. But that was the most challenging — the emotional stuff was the most challenging. I think the most rewarding was just seeing the whole thing put together, just the whole cast and the stories, and everybody coming together. That was the most rewarding for me.

And how is your character dealing with Mia's absence? How has your storyline progressed without her?

MC: I'm grieving! She's still there with me, and I'm still very much grieving over her. I'm coping.

THEN: A few years later, you and Regina reunited for When the Bough Breaks and had amazing onscreen chemistry, just like we remembered. What was it like filming in New Orleans, and did you get to experience any of the nightlife during your downtime?

RH: We liked filming in New Orleans! But these two [points to herself and Morris], we don't do nightlife.

MC: We don't.

RG: We're not out late.

MC: Well, there was a day when...damn, that's crazy. God rest his soul. Remember you and Michael K. Williams went out during Mardi Gras?

RG: Yeah, we did Mardi Gras!

MC: They didn't invite me, but yeah.

RH: Another fun day I remember with Morris, when we were shooting — remember the beignets?

MC: Oh yeah! It was the whole bag.

RH: We couldn't stop eating the beignets.

MC: They were so nice and warm!

RH: Whew, they were good [laughs].

NOW: Lastly, I noticed time doesn’t seem to matter when it comes to The Best Man franchise, because years will go by in between projects, and fans still show up eager and ready to watch. What does that mean to you as an actor, and what are you hoping fans will take away from The Final Chapters?

RH: Well, that feels great! You have fans who support something you do for decades? I mean, that's the biggest reward of all.

MC: It really is. I don't think anybody who's done every single movie that they've done have people who have just been waiting to see it. To have a project that spans over the length of time that this has and having people eagerly anticipating seeing it, it's very rewarding.

RH: There's no words for that. People don't get to see what that means to us, but it's why we come back. We get excited. It means so much to us because we want the fans to be happy and satisfied.

As a fan, I can confidently say we are both happy and satisfied!

For more of Morris and Regina, be sure to check out The Best Man: The Final Chapters. All eight episodes are now streaming on Peacock.