Regina Hall Looks Back at Her Most Iconic Roles

Welcome to Look Back At It, a monthly column where some of the most iconic Black actresses in Hollywood reminisce and reflect on the roles that made them stars. For this month’s installment, Regina Hall breaks down her career—from the Scary Movie franchise and Girls Trip to her most recent film, Honk for Jesus. Save Your Soul.

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“It’s really interesting to see my evolution,” says Regina Hall as we slowly parse through her two-decade-long film career. “It’s weird to see yourself change and grow. Starting from The Best Man and ending with Honk for Jesus, I went from a stripper to a pastor’s wife.”

Since her debut in 1999, Hall has starred in comedies, thrillers, and what she affectionately calls “hood classics.” From Love & Basketball and Paid in Full to Think Like a Man and Scary Movie, her talent knows no bounds. And throughout the years, her career has only gotten bigger. In 2017, her film Girls Trip became the first Black-led movie to make over $100 million at the Box Office. The following year, she won the New York Film Critics Circle Award for Best Actress for Support the Girls, making her the first Black woman to receive that award.

As she looks back at her career, she can’t help but beam with pride. “I’m proud of all of it,” she says. “It’s amazing to see this continuing journey. I always get excited to see what’ll be next, but I’m always a Black woman out here trying to represent us as best as I can. I guess the thing that sticks out the most is that, minus two, my mom got to see them all. My dad didn’t get to see any because he passed when I was young, but my mom saw most of them. So [these roles] are all my babies. You can’t really pick a favorite child.”

Below, Hall takes us through her most iconic roles.

Candy in The Best Man and The Best Man Holiday (1999 and 2013)

“This is incredibly special. It was my first studio film and it’s where I met so many friends who have been lifelong. Pretty much all of them. This was the beginning. It’s the thing that brought me to L.A. and it was a big deal. I didn’t know what the movie was or who was in it. I didn’t even get the whole script, so it was a surprise to book it. And then, obviously, The Best Man Holiday was two decades later. And Candy was able to come back and be in the sequel. I only worked two days on the original. [Laughs] Well, it actually ended up being a few weeks because the wedding scene went long, but now she feels important in the grand scheme of things. So it was a great beginning and a great reunion. And Malcolm D. Lee [the director], who I worked with on Barbershop and Girls Trip ended up being a major part of my career. We also have The Best Man: Final Chapters releasing this December on Peacock.”

Lena in Love & Basketball (2000)

“Love & Basketball was my second movie. I just love this film. I also met another first-time director, which was Gina Prince-Bythewood who I ultimately worked with again on Disappearing Acts. By this time, Sanaa [Lathan, her co-star in The Best Man] and I had become really close, so this was another exciting movie. You know, Gina thought I was an actual stripper in The Best Man. She was like, ‘How’d they get a stripper to act?’ So she was very hesitant about casting me because she thought people might remember, but no one did.”

Brenda in the Scary Movie franchise (2000-2006)

“It depends on how you look at the phrase ‘breakout role,’ but Scary Movie was definitely it. This was incredible. It was from these movies that people started to see me as a comedic actress. For me, what stands out is the Wayans family. I was such a fan of Keenan Ivory Wayans and I’d watched In Living Color, so to work with them and have Keenan be like, ‘I think you’re funny,’ I can’t tell you what that did for me as an artist. I learned so much from that. Keenan was really profound in how far and how comfortable I felt in pushing the idea of comedy. I played Brenda four times. And it’s been great to be able to reach younger generations and to still have relevance for a movie that’s over 20 years old now. These make me profoundly happy.”

Keisha in Paid in Full (2002)

“The fact that you can have a hood classic? Wow. [Laughs] I mean, Wood Harris is such a phenomenal actor. Mekhi [Phifer] was amazing. This movie is also where I met Charles Stone III, who directed two of our Best Man episodes and I worked with him on Black Monday as well. Ironically, the young woman that I played actually went to my school. So it was bizarre. But I love this movie. I didn’t do a lot because it’s really the guy’s story, but the fact that people still love that ‘I’m boring, too’ scene with Keisha and the fact that I had that kind of connection and chemistry with Wood who I was a huge fan of, was great. So this is another classic.”

Kelly in Law Abiding Citizen (2009)

“This was a fun ride. I got to work with F. Gary Gray and I was a big fan of him, Jamie Foxx, and Gerard Butler. This was a surprise because I didn’t expect to get this movie. I remember I was really annoyed that my agent had made me go audition for this. I was like, ‘You know I’m not gonna get it.’ So this is a great memory. This was before you did a self-tape, so I went into a casting room with Joseph Middleton, who I adore. I actually loved having casting directors in the room because I always found them to be helpful. But with this one, for my audition, I had to do a light scene. I don’t remember the scene exactly, but he was like, ‘I actually want you to do the opposite and make it heavy because you’re so known for comedy. You have to go against the levity of the scene.’ And when I got the job, F. Gary was like, ‘I didn’t even wanna look at your tape. Your agents kept harassing me.’ [Laughs] So this was a fun and wonderful experience. It was cold in Philly, but outside of that I loved it.”

Michelle in Death At a Funeral (2010)

“I loved the original and I was really excited to get to work with Martin Lawrence. I had met Zoe [Saldana], but never worked with her. I was a fan of everyone, really. This was a wild movie. It was one of those movies where you had one outfit the entire time because it was all day at the funeral. But it was so smart and not something that you necessarily get to see us do a lot. So I was really excited to be able to do this project and I have great memories from this set. I’ve gotten to work with so many comedians and talented people during my career. I feel really blessed because I’m always getting to learn something.”

Candace in Think Like a Man and Think Like a Man Too (2012 and 2014)

“I love everyone in these movies. The first one was great. This was actually the first movie that I did with Will Packer, which obviously led to the Think Like Man Too, About Last Night, Girls Trip, Little, and the Oscars [this year]. So this was the beginning of a huge relationship with Will Packer Productions. This is a movie that my mom and my aunts would watch over and over again. It has a lot of really wonderful memories. This is what really led to Kevin [Hart] and I working together on About Last Night. I feel like we really bonded on this movie and people saw how great we worked together comedically. The first Think Like a Man was incredible because no one was expecting it, and I loved Taraji [P. Henson] and I as best friends; I loved [our] dynamic.”

Laura in When the Bough Breaks (2016)

“This was fun. I loved Morris [Chestnut] from working with him on The Best Man. This was the first time I had gotten to do a thriller. We had a really good time in New Orleans making it. The jazz was sweet, but I think I ate too much. [Laughs] My wardrobe didn’t call for anything, so I was like, ‘Let me enjoy this food.’”

Ryan in Girls Trip (2017)

“I remember I was on a plane doing press for About Last Night. Will was on the plane and he’s like, ‘I got an idea for this movie.’ They were still working on the script [at the time]. Then when we started filming, we really forged a friendship on set that was really joyful. Obviously, I’d been a fan of Jada [Pinkett Smith] and of Queen Latifah. I don’t know what expectations I had for the movie. I won’t speak for the other cast because they may have been thinking, ‘Oh, it’s gonna be great.’ But I’m talking about its reach. I didn’t know we would reach so many people. I just remember we were like, ‘We’re Black women and we’re getting to do a comedy that’s gonna be a hard R-rating and we gotta represent us. We gotta do a little class and a little crass, and then have fun so that all women are able to experience it with their girlfriends, whether they’re Black, white, Spanish, or Asian.’ It could be universal, but you also could feel like you’re watching Black women. So this is a really, really special movie. I love it. It was so much fun to make. We laughed a lot. It was a very special moment in time.”

Lisa in Support the Girls (2018)

“This was right after Girls Trip. I read this script and I kept reading it and waiting for a bad moment. Like, ‘Lisa stole it, Lisa did this.’ I met with the director and he didn’t write anything racially specific in the script. It was an easy story that you could have made salacious. And he just gave all the women so much heart. He was able to create a community of sisterhood. Lisa was just good. It was that slice of life that represented hard-working people, just being. I remember thinking about how cathartic the ending was with them leaving the place. It was a small move, but it’s the small moves that are usually quite profound in our lives. I felt like a mama bear around all my little young babies who worked beside me and who are just so talented. I loved working with them. In combination with Girls Trip, this was really important for my career from a critical point of view. So this was a profound experience, both personally and professionally.”

Maya in Shaft (2019)

“I got to be the baby mama to Shaft, the Badass of All Badasses. I love this movie, but it disappoints me. A lot of people didn’t see it. But I loved the way Tim Story took Shaft and brought together three generations. And I’m such a huge Sam Jackson fan. I think people didn’t know what to expect from this movie. They thought I was going to be a different kind of Shaft girl. But then when they saw it, they were like, ‘I laughed out loud.’ I just thought it was a really fun movie.”

Jordan in Little (2019)

“Well, this is hard because I’ve never liked Issa [Rae] or wanted to work with her. [Laughs] No, but this was a special one because Marsai [Martin] came up with it and I love Issa. I got to executive produce it. And this was different because Jordan was a monster and I loved having the audience see me as bad. She was unapologetically horrible. So I had fun. Marsai and I thought of things where she would watch me and I’d watch her. She felt like a little version of me. I loved this movie and had a great time in Atlanta.”

Trinitie in Honk for Jesus. Save Your Soul. (2022)

“I mean, what can I say? This was with another first-time director, Adamma Ebo. I loved working opposite Sterling [K. Brown]. I loved the point of what the film was trying to say and its message. I loved playing Trinitie. This was a fun movie to make. There was a depth to the story and characters that you didn’t expect. You had compassion for them. There was no villain and no hero. Like I said, I feel blessed. Every time I get a project, I feel like I get to work with someone who teaches me. I hope this eventually becomes a classic.”