‘Black Monday’s Regina Hall Leaned Into Ruthless Ambition Of Second-Tier Wall Street Trader For ’80s Showtime Comedy

When Regina Hall read the pilot script for Black Monday, the ’80s comedy from Jordan Cahan and David Caspe, she immediately fell for the character of Dawn. A leading trader at a second-rate Wall Street firm, Dawn operates within a toxic boy’s club environment and gives as good as she gets. “I loved that she’s just as ruthless and ambitious,” the actress reflects. “She’s one of the guys, [and] also very much a female.” While pulling back these layers, Hall worked to find her footing in a unique comedic space, which shifted unpredictably between the grounded and the absurd.

What excited you about the idea of working on Black Monday

What excited me was Don Cheadle; he always excites me. I don’t know if that sounds good. [laughs] A little #HeToo-ish. But I’ve always been a huge fan of his work, and loved how he was so brilliant, dramatically and comedically. So, the fact that he was a part of it was already exciting. Then, I read the script for the pilot and was like, “What the hell is this?” It was this world that I loved, and I thought that it could be something that was really special, because the comedy that could come from a period that we’re observing retroactively was really appealing and interesting.

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Why was Dawn an appealing character for you?

 I loved that she was a woman [who] was brash like the boys—that she was incredibly smart, but she also never felt above the guys. That she could do dirty humor, and they didn’t make her the school mom of the group. Like, “Hey guys! Don’t do that.” I loved her being in the ’80s and wanting her career, as opposed to just wanting marriage and kids. I just thought she was dynamic and had a lot of layers. But more importantly, for this kind of show, I thought she was funny.

Black Monday constantly subverts tropes and expectations of gender, in relation to its period setting. It’s interesting to watch Dawn fight for her career, as her husband pushes for having kids, going so far as to poke holes in condoms when she’s not looking.

Yeah. I felt like even when I looked at the scripts weekly, there’d be twists and turns that I didn’t expect. I love that her and Mo [Cheadle] have the most beautiful, unhealthiest relationship. [laughs] It’s awful. When I read the first episode, I knew they had feelings for each other. But that second episode, when she’s trying to get her promotion…The idea that they’re in an office where they’re constantly one-upping each other, and it’s so normal, and everyone around them is like, “Oh, it’s Dawn and Mo,” I love the way they handle all those things.

What did you make of the series’ damning critiques of ‘80s pop culture? It has certainly become difficult to watch certain classic films of the period, given today’s social context.

It’s crazy because until this show, I hadn’t realized what happened in Sixteen Candles. There’s so many things where I’m like, “That’s crazy, what we were watching and loving.” I love the way they take a look at everything, and they don’t make a message, or make it judge-y. It’s just like, “Oh.”

Black Monday uses its period setting as a vehicle, to allow for the discussion of topics that are much trickier to tackle in 2019. Has comedy become a more challenging space to work in, nowadays?

Oh, absolutely. There are definitely things that were said and done before that you just could not do now. In some ways, comedy makes a lot of things more digestible, but I’m sure that especially for stand-up comedians, it’s difficult. [With] comedy, I kind of always felt like, if they made fun of everyone, then it didn’t feel strange. But these are times where there are a lot more voices, and you have to hear people’s feedback, and be responsible in a way that you didn’t have to [before].

One of the episodes I loved in the show was the sexual harassment seminar, because it didn’t really exist back then, you know? I mean, it did; obviously we made it extreme. But not in the way where now, even before we start a show, we have those human resources meetings…It always takes extremes before balance comes.

Tonally, the series is in its own universe. How did you find your way through scene work in the first couple of episodes?

I think we were all figuring it out. There are certain things on the show that deal with issues that are real—personal life, love life, and classism. There’s so many things, and these characters are also incredible flawed. You have these people that are not the nicest, but you need an audience to like them. I think it’s kind of showing the humanity of the characters. What was great was, we all were doing it together in the first season. We were all like, “Let’s try this,” and we had writers who were willing to try anything. You hope that it hits the mark, but I think that’s what made it exciting. Because we were like, “Is this going to work?” [Laughs]

Executive producing the series, Seth Rogen and Evan Goldberg also directed the pilot episode. What have they brought to Black Monday?

They really set the tone. I found for me, and for Dawn, working with them, I got it. They let me know the tone that the show was going to feel like, how far we could take the humor, how grounded it would be. Even though these situations [present] such extremes and decadence, it was still grounded, and that helped a lot. I remember the first time we were on set, there was a big office scene where Mo is like, “I am black Moses,” and I think we all kind of knew what that tone was. Because he’s serious, and they’re buying into it, and I’m like, “Ugh.” But this is a world where we can be free, as long as it feels like these are real people.

It was great for me to be Dawn because she never felt like a victim. So, even when [a co-worker] made comments about her tits, she never felt like a victim of his sexual comments. I mean, she made worse ones of her own. I loved that they were like, “Add what you want, make it your own.” Then, I knew that the amount of ad-libbing, they loved that. They really set that tone, and they were great.

Did you enjoy all the improv that came with making this show?

It was great. Jordan and David love improv. Paul [Scheer] is amazing at it; Don is amazing, and Andrew [Rannells] and Casey [Wilson]. I think we just have a cast that’s really funny. They’re funny people. So, whatever we have written, after the first take, we’re just doing craziness. And that’s what’s fun, because as we discover our characters, we get to discover what we might say. Improv work requires freedom. You have to feel like you have a safe space to try it. So, we try it, and one improv might lead to another one—or even if it doesn’t lead to a comment, it leads to a reaction.

There’s so many times where we’re cracking up in a scene because it was an improv line. I don’t know why we enjoy how debaucherous each of us is, but we love that. It’s kind of like this really funny, and yet sad family. There is something endearing about each and every one of those characters, even Tiff. I mean, she has a line where she’s like, “Daddy used to always say, ‘Nothing ruins a brand faster than seeing it on a bum.’” She smiles, and it’s awful. But you love it, because you understand who she is, and what she comes from, and why she has these beliefs, and you get that she represents that.

So, I love all the characters, and the way that they’re handling being in this boys’ club with intelligence. No one’s made fun of for their flaws, and that’s what I love about it. And they’re all friends—unless there’s business involved, and then they stab each other in the back. But other than that, they all really love each other.

Did you enjoy tapping into the ‘80s through Dawn’s wardrobe, makeup and hair?

Oh yeah, so much. It was so much fun for me to be in the ’80s. I ate too much, because those shoulder pads and belts didn’t make me realize that I was getting bigger. Then, I got home and got in my own clothes, and was like, “Wait, nothing fits.” But I loved it. I love the music in the ’80s, and the hair. I’m having a little too much fun with all the bows in my hair, but I like it.

Reportedly, you shot all 10 episodes in 10 weeks. Did Season 1 feel like a bit of a sprint?

It was a lot of work. We were there a lot, but it was also really fun. I have to say, it went so fast, [because] we all got along with each other. We block shot, so there weren’t really a lot of days off, but I think that intensity and pressure also felt like the intensity that’s in the show. There’s a lot that happens. It’s dense, and there’s a lot of dialogue, so we just would have to be on it. But like I said, I think it’s the same thing that serves the show.

Black Monday will be back for a second season next year. Where are you at with that now?

The writers are back in the writers’ room. We’ve spoken; I’m going to go to the writers’ room myself, and we’ve gotten some ideas about what’s going to be next, what portion of these characters’ journeys we pick up in.

At the end of Season 1, underdogs Blair and Dawn have found themselves in new positions of power. What are your thoughts on Season 2, and your hopes for it?

Well, it was exciting for me, until Blair turned into a vicious cokehead. [laughs] So, now it’s kind of that season, watching where it goes, knowing that the algorithm has caused a complete crash—picking up in the middle of chaos. It’s a little scary for Regina to think of Dawn, because there’s no Mo. I think it would be the first time where Dawn would have to see if she’s actually able to navigate [independently]; it’s different to think you can navigate, than to actually navigate it. So, I’d love to see how Dawn’s going to handle no Mo, and a dark and naïve Blair. It’s all kind of scary, if you ask me.

Black Monday is the first series you’ve produced. What has the ability to contribute behind the scenes in this sense meant to you?

It’s really been great. I’ve always been fortunate enough to be able to have my opinions heard, but to be able to actually be a part of the process—and feel really comfortable and welcomed, because you feel like your opinions are valued—is so great. I’m really grateful, and actually, I really like producing, so I hope it’s something I can continue to do. 

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