‘Black Monday’ Star Don Cheadle Talks Trump & The Showtime Series’ All-Too-Real Dark Comedy

Dino-Ray Ramos
·9 min read

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From playing the unhinged Mouse in Devil in a Blue Dress to battling Thanos as War Machine in the Marvel Cinematic Universe, Don Cheadle’s resume is a diverse array of characters, but none of them are quite like Mo Monroe in Showtime’s Black Monday. Cheadle plays the coke-snorting, self-destructive broker navigating the stock market crash of October 19, 1987, which of course came to be known as ‘Black Monday’. Now in its second season, Cheadle discusses how the series reflects the current landscape, and how the global pandemic and America’s civil unrest will affect the industry going forward.

DEADLINE: How do you think Black Monday can serve as a cautionary tale, or a reference for us to learn from?

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DON CHEADLE: Some people come up and they’re like, “Wow, that’s a cautionary tale,” and other people say it’s a primer for how you’ve got to get it done. It just depends on who you ask. Some people think that sounds [like] the greatest, most fun time in the world, and it’s not. People’s lives are destroyed. The show is a comedy and we’re doing it for jokes, but it’s being really pushed.

In one of the books that I read the author was saying, even with all the regulations, that this is cyclical stuff. The stock market crash and those kinds of things are cyclical because we’ve never fixed the inherent problems in society that address the highs and the lows and the haves and the have-nots, and those who are able to take advantage of every opportunity and those who will never have opportunities. It’s not like it’s something that’s foreign. The one thing that we’ve never really excised from the process, and you can’t, is human greed.

So, wherever there’s a way to shoot an angle, wherever there’s an opportunity to get over on something, people are going to be looking for it, and that’s a business particularly designed to allow for it because the upside is so huge. It’s worth it. If the game was not going to be that big, it wouldn’t be worth going for that huge risk, but you stand to make an ungodly amount of money if you cheat the right way… You pay the right people off and get away with it.

DEADLINE: Black Monday spotlights cyclical behavior that has strained the country in more ways than one. Right now, there is a shift with protests stemming from the death of George Floyd and a call to action over racial inequality. On top of that there’s a pandemic. How do you think all of this is going to be reflected in storytelling and the industry?

CHEADLE: I believe all that we know is that it will. I don’t know if we have enough evidence to be able to point to how it will. For some people, it was already a part of what we were attempting to do. I’ve had a diversity mandate with this crew that I’ve put together, and shows that I work on for years. My sets tend to look like the world and the United States. You have a lot of people who have the positions and keys that wouldn’t necessarily be getting the opportunity.

I think people are realizing, “Oh s**t. I didn’t know we were a part of the problem.” Hopefully from soup to nuts, every aspect of every business will ask, “Where have I leaned into this bias and where have I not done my part?” and not just, “Be a good person.” A good person means actually trying to take things apart that aren’t working. It’s trying to attack injustice wherever you can, where you are. So, if those things become in some way, codified in our business, outside of things like diversity mandates, and the recognition of the disparity that we have in certain positions, we’ll be able to point to when and why it happened, but that remains to be seen en masse. I don’t know that that’s going to happen industry-wide because we’re still in this moment and people are not sure what to do. Obviously, the concern is things tend to revert and go back to the way they were because we are humans. It’s hard for us to keep this sort of attention span around things that we’re passionate about.

The forces that didn’t want the change to happen in the first place don’t sleep. They’re not kicking back. And they’re like, “Okay, well, how are we going to come out of this still running s**t?” That’s always the challenge in these moments: not to let that energy abate, not to go back to sleep.

DEADLINE: What was it about Black Monday that really appealed to you in the beginning?

CHEADLE: I love the distance that the period piece gives us, which allows us to look through a particular lens and see how far we’ve come, and how far we have not come. I think we’re seeing this played out in our news right now. Since Trump has been President, it has made our show incredibly bridged with that sort of perspective. It was dealing with the wish fulfillment of a group of people that probably would not really exist at that time. I don’t know if they would exist now, but the ability to use this different grouping of actors and characters to try to tell a very, in some ways, American story about greed and loyalty, or disloyalty, and play with that. I just thought it was a great opportunity.

DEADLINE: Your character Mo is an anti-hero. But was there a part of him that you connected with?

CHEADLE: Well, I think in some ways when you play these anti-heroes—not just for the people who are playing them, but the enjoyment of watching them—you get to live vicariously through their actions and ways that they do things that you would never do or say, but sometimes you feel like it. Mo is driven by his id. He doesn’t have a filter, and he really hasn’t recognized, for the most part, those sort of niceties that would prevent us from doing things that we know would feel good, but we probably shouldn’t do. I have a very smart friend who said a wise statement: “If it feels good, don’t do it.”

DEADLINE: How has making the show evolved for you?

CHEADLE: I couldn’t have anticipated, other than just understanding the metrics by which you get things done, how much the workload would be, the impact that that would have, and trying to accomplish something on a five-day schedule. That is very, very difficult. How that pressure and the frenetic energy of that would lend itself to the narrative. I think that it’s a very sweaty show. It feels like everybody’s on coke [Laughs].

We weren’t all doing drugs. It’s just the way that we all had to approach this to get it made. The cutting style, the shooting style, and the rapid-fire dialogue. We’re trying to make things happen within a certain time frame… It feels like you’re on drugs to me when you’re watching this show, and that’s become part and parcel of the storytelling, and the insanity of who these guys are, and what it is they’re going through.

DEADLINE: How did you immerse yourself, besides the fashion, in this very particular period of time? What do you remember about the era?

CHEADLE: We do what we usually do, we read articles, we listen to the music, we look at the fashion, we try to build out who these people are and what they were. The bible is the script, what the pilot is, what the [writers’] room puts out, and what they’ve done. As we go into production, all the people that make it feel like it does, they’re all doing that research too so you’re steeped in it by the time you show up. And David Caspe, who’s one of our writers, his dad was actually a Wall Street trader during the period. So, we were able to bend his ear a lot.

Mo is doing crazy s**t, but he’s doing crazy s**t at a time when everybody’s been doing crazy sh**t. There are no real regulations. I have friends during that period who were actually [trading] and as they reflect now, they’re like, “What was I thinking?” It wasn’t enough to kill on your side of the trade, you had to kill the other person on the other side of the trade. There was a zero-sum game. That was a part of it. That was a part of the bragging rights. That’s a part of how you knew you did a great job—not only did you achieve what you were trying to achieve, you destroyed. The excess was just over the top. One of my friends, who was way overweight and had a lot of health issues, he realized that he was going to die if he didn’t get off of that hamster wheel. And when he got off, and finally looked back at it, he was like, “I was out of my mind.”

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