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Regina Hall on Black Monday’s Finale Twist and Why She Loves to Troll Issa Rae

Photo: Arturo Holmes/Getty Images

For two seasons, comedy superstar Regina Hall has delivered a knock-out performance on Showtime’s Black Monday as Dawn, a hilarious and intelligent Black woman trying to climb up the ladder of the white boys’ club known as Wall Street. Despite her best efforts, Dawn does not end up at the top of the food chain at the end of season two, but (spoiler alert!) she’s locked up, having taken full credit for the titular Black Monday scam in order to help her on-and-off again beau Mo (Don Cheadle) avoid life in prison. To have Dawn, the brains behind the Jammer Group firm and the heart and soul of the series, end the season in an orange jump suit instead of one of her signature ’80s shoulder-pad ensembles was something even Hall didn’t see coming.

“Dawn just never gets it right,” Hall joked as she discussed the season finale. The actress, who’s career includes such hit films as Girl’s Trip, The Hate U Give, and Little, hopped on the phone with Vulture to discuss Dawn’s unfortunate fate, the enduring influence of Brenda Meeks and the Scary Movie franchise, trolling Issa Rae, and whether or not she and Mo will ever make their relationship work.

We’ve gotta discuss the twist ending. To protect Mo, Dawn goes down for Black Monday and winds up in jail. What went through your mind when you got that script?
I was like, “Oh, no. Dawn just never gets it right. No credit for Black Monday, prison.” [Laughs.] But I didn’t see it coming, so I always like that. And I did like that it was another layer of Dawn and Mo’s relationship. Her understanding that those three strikes would have put Mo in jail. And it’s not like they get the happy ending, but it’s another level and element to their connection and their love for each other.

I think Dawn and Mo’s relationship is one of the most complicated and interesting will-they, won’t-they romances on TV right now. It’s pretty clear to me why Mo keeps coming back to Dawn: She’s smart, talented, beautiful. What keeps pulling Dawn back to Mo?
Mo, honestly as crazy as he is, I think he loves Dawn. And she does know that. And she understands his damage and neuroses as she has the same ones. Although they can’t trust each other in business, there is a fundamental trust that they have. Even though Mo had a deal going with the FBI, he always tried to keep Dawn safe. It feels like they’ll cross any line when it comes to money, but they don’t want the other to suffer. Dawn knows that Mo can go to the lowest depths, but he doesn’t with her. It’s like the two of them against the world … when they’re not against each other. [Laughs.]

There were a lot of nuanced and hilarious conversations about race this season, like the double date scene with Dawn, Mo, Marcus (Dulé Hill), and FBI agent Connie (Xosha Roquemore). What’s it like to get to work on that type of material?
Well, the fun of it is that it’s very true to the time period, but it’s also really still true. We were talking about that same conversation of voter fraud that was happening in the ’80s, and we’re still talking about it, maybe actually even more now. Maybe we weren’t talking about it as much ten years ago even though it existed. But now it’s incredibly… [phone rings]. Hold on one second. [To mother:] “Hi, Mommy I’m doing a phone interview, I’ll call you back in 15 minutes. I love you.” Sorry.

No, I love that. Please tell her I say hi.
Thank you. [Laughs.] It’s all just incredibly relevant now. You know, we’re looking at Blair and dealing with his sexuality and everything. It’s real and it’s true and we’re even seeing it now. Even the Casey [Rose Wilson] story line with the crosses on the knees. It’s like we have this segment of the population that is so extreme … there’s quite a division. But, you know, it is fun to play, because as we do it, the writers and then the actors on set get to ad-lib with so much of what’s going on. And then I love that [Connie] is, here it is, a Black woman who is actually the FBI agent. It works even better than if she were, you know, white. They think they’re in one conversation at the table, but there are two different points of view.

Absolutely. I must say, I love that your mom called because my mom was a Black woman working in finance in the ’80s and ’90s and I’ve never really seen her represented on screen until Dawn, basically.
Was she? That’s so amazing.

Yeah. The stereotype of Wall Street in the ’80s is that it was dominated by white, straight men, yet Black Monday has found a way to tackle the finance industry while being one of the most subversively queer, diverse, and Black shows on television. Was that always the intention or did it develop over time?
You know, I don’t know that that was the intention when they were creating the show. But once they got the cast, they realized where they could go, what they could play with, and that was what changed the voice. Being like, Well, what was it like navigating the reality of what existed? I think that’s when they decided to explore with Keith (Paul Scheer) and his character being married and Jewish and thinking, “Well, that’s really not my truth.” And then Blair (Andrew Rannells), who is literally in politics and then falling in love with a congressman who calls his wife “mother,” ironically enough. There are certain subliminal messages there. [Laughs.]

[Black Monday] shows the reality of how these worlds don’t allow us to be who we fully are and explores the nature of how these people and lives intersect in that space. Clearly, this is a cutthroat world. What the writers did that was smart was make the firm a place where no one else would hire any of us. Then we got to be the Bad News Bears of Wall Street.

And band together.
And band together, even though we destroy each other. [Laughs.]

I don’t know if you’ve heard this, but one of my favorite podcasts, Las Culturistas, just named their top 200 moments in all of culture, and you were No. 4 for your incredible role as Brenda Meeks in the Scary Movie franchise.
No! [Laughs] That is the best!

How does it feel to know something you made 20 years ago is still in the Zeitgeist today?
That is so amazing. Me and Anna [Faris], we used to have so much fun, and I really love Brenda. She’s one of my favorite characters. But I used to say to Anna, “Why do you think Cindy’s friends with Brenda?” Brenda is so selfish and so awful. I remember the scene where I wanted the skeleton to kill her, and I’m like, now, why are they still friends? I literally prayed for her death. [Laughs.]

Yeah, you really do pray for her death in that scene.
And it was genuine! My character really didn’t care [about Cindy]. I just wanted to leave. But, I mean, I love the fact that new and younger generations still respond to the movie and are discovering Brenda. To me, that’s the best. Being a part of projects that resonate with, honestly, what a lot of Gen X and millennials are going through — movies like The Hate U Give. Even now, [millennials] have been such a big part of Black Lives Matter and LGBTQ issues, there are so many places where people have raised their voice and I think it’s so important. So yeah, it makes me proud.

Absolutely. If I’m not mistaken, you’re about to play a queer Black college master at a white institution in Master.
I am. I have this … well, you have to see it. I can’t say. We’re not done. We got shut down because of COVID. We were filming in New York. I don’t know when we’ll finish, but I also have Tijuana Jackson: Purpose Over Prison with Romany Malco which comes out July 31. And then another movie called Breaking News in Yuba County, which I don’t know when that would come out. And then something else I’ll be going to shoot once we get the date. So it’s all kind of, I hate to say COVID contingent, but we’re working around COVID. Listen, my thoughts and prayers are just for everyone who’s lost people and jobs.

One hundred percent. Before you go, you’re known to be quite hilarious on set, specifically with your Little co-star Issa Rae. Are you a troll on every set?
[Laughs.] I love to troll Issa. I’m like the bad older sister. Like, she should be doing it, but I end up doing it to her. But she does it too! I said to Issa, “I’m going to make a video of you and all your trolling moments.” You know, we just like to have fun. You’re on set for a lot of hours and it’s great when there are people you get to have fun with and just enjoy and feel comfortable around. It naturally happens. And Issa’s so hilarious, she always gets the joke. But she always has a subtle one right there, waiting for me. We have fun going back and forth a lot.

Last question because I know you’ve gotta call your mom back. Do you think Mo and Dawn are gonna make it?
Oh, gosh, I hope so! I want them to make it, but then I’m like, they might be awful together. They’re actually kind of terrible, but wouldn’t it be great if they could make it?

This interview has been edited and condensed.

Regina Hall Didn’t See Black Monday’s Finale Twist Coming