'Black Monday': Don Cheadle Breaks Down the "Insane" Plan at the Show's Center

Black Monday-Publicity Still-H 2019
Michael Levine/SHOWTIME
Don Cheadle’s impulsive Maurice “Mo” Monroe is at the center of a brewing storm on Showtime’s Black Monday, which tells a very fictional version of the year leading up to 1987’s stock market crash. Though Mo is a successful trader with all the excessive trappings to show for it — unlimited cocaine at work, a robot butler at home — he and his firm are second-tier, locked out of the truly privileged and largely white inner circle. 
Mo’s convoluted plan to finally break into the big leagues involves a hostile takeover of designer jeans company Georgina, which he intends to pull off by hiring hapless Wharton graduate Blair (Andrew Rannells). Georgina is owned by the family of Blair’s girlfriend, and Mo believes he can manipulate his new hire into giving him a majority stake. But the structure of the show means that we know Mo’s plan is not only doomed to fail, but also doomed to cause the worst single day in the history of the stock market.
“The main aspect of Mo’s personality is to shoot first — he's definitely shoot, ready, aim,” Cheadle tells The Hollywood Reporter. “If he was a poker player, he would rather have all of his money in the middle, waiting on the cards to come to make his hand good, rather than someone who knows they have a great hand and goes in. And as we know, it can’t last. The wheels, at some point, have to come off when you deal with business in that way.”
Cheadle discusses Mo's "insane" master plan and motivations, his relationship with Dawn (Regina Hall) and finding the right line for the show’s politically incorrect humor.
In this episode, Mo explains that his plan is to form a "father-son bond" with Blair to manipulate him. It's pretty dark — do you think he has any qualms at all about what he’s doing?
No, I think Mo has his eyes on the prize, and whoever has to get run over on the way, it’s like, "Hey, kid, this is business." But it's not only that he would do something like that, it's the fact that he thinks it's just that easy! All I have to do is become this guy's friend and be his father figure and then I'm gonna take over. It's like ... that's your plan? Become this guy's father figure? That's the whole thing, and then you're gonna get control of his girlfriend's family’s empire? What are you talking about? That doesn't make any sense! It's insane!
It's cocaine logic.
Absolutely! And if he didn't have someone in the company like Dawn, who's this centering character for him, they probably would have been belly-up many, many years ago. People have been asking me how Mo is unlike Marty in House of Lies, because they're both guys who really go for it, and I'm saying: Mo is insane! Marty was not insane. He would risk things, but Mo pushes all his money into the middle and is banking on something as tenuous as "I'm gonna make this guy like me." That has nothing to do with how business works, but to him it makes total sense.
Why is he so mercenary and ruthless?
I think he really has a huge chip on his shoulder. I think if you were to put Mo on a couch and do any sort of psychoanalyzing of him, you would find out pretty quickly that he doesn't think that much of himself. You see that a lot with these characters who have all this bravado, walking around like they're running the spot, that they have a very deep fear, and a deep sense of not actually being as good as they profess that they are, and a big concern that they're going to be discovered at any minute. I think that's what Mo is running around with, like, "I'm a charlatan and everybody's gonna find out in two seconds." 
Is that what he's doing with the screenwriter in Sunday's episode, too, trying to perpetuate this myth of himself?
I think he wants to control the narrative and create the mythology in every way he can. He keeps saying, "I'm as good as so-and-so; I'm as good as all of these people," and you only need to say that over and over and over again if you really don't think that's the truth. If you really believe that, you're not standing on every corner screaming it. It's deep, deep insecurity with him.
Mo's relationship with Dawn is interesting — she's a stabilizing influence, but the show never makes her a nag. 
Exactly. She's like, "I'm fine with crazy ideas, you just gotta let me in on the crazy ideas so that I can help you craft the crazy ideas." She's not against the crazy, but Mo's kind of crazy without any sort of balance is just too much. We definitely wanted to make sure, and Regina was always very clear about making sure, that she's not the finger-wagger in the scene, or the one that’s always going, "Ugh, come on guys!" That becomes really tedious, and it's not fun for her either. We have an HR meeting in one of the upcoming episodes that of course, with this group, is the worst HR sexual harassment meeting you could ever imagine, and she's one of the worst violators! Any time you get to play with Regina is a lot of fun; she's really funny and generous and super quick on her feet, great with improv.
Did you improvise a lot on the show?
Yeah, we all did a fair amount. Once we were shooting it, we'd lock it in and knew where we were, but I think we found a lot of stuff through improv. David [Caspe] and Jordan [Cahan, the series creators] are very open to that, and we were always encouraged to play, which keeps everything very spontaneous. I think you can see it in the show; it just feels like it's on fire all the time. We just wrapped last month, and I'm still trying to decompress from a lot of it. It all happened so fast — we shot 10 episodes in 10 weeks, which is insane. I was trying to count the hours that we work a week, and if I'm doing 60 hours, the crew's doing even more than that, so it was really a whirlwind.
A lot of jokes in the show are incredibly un-PC. Was there ever anything where you had to say "This is too far"?
All the time! Every day. Every scene. Every episode. You should hear the jokes that didn't get in. Things where I was like, "Nah, we can't do that. I can't say that. That's too much." That's the fun of the show, and kind of the challenge of it too where you talk about PC — I don't have a problem with it, because I think being PC is just basically not being an asshole, and I'm cool with people trying not to hurt other people's feelings. But if these characters were PC, it wouldn't make any sense, and it would be untruthful for the time. You look at a John Hughes movie now, or Revenge of the Nerds, and it's insane how inappropriate what's happening is. These are popular movies for kids, and there's a scene where one of the guys sleeps with another guy's girlfriend in a Darth Vader mask and she thinks he's her boyfriend and he's not. He's basically raping her! It's like, this was family entertainment! One of the fun things about the show is to look back on that period and skewer a lot of those things, and hopefully people remember that and kind of juxtapose it to where we are now. 
Were the cast told who dies at the beginning of the premiere?
Some of us knew, but not everybody. That's another thing that's fun about the show, the mystery inside of the comedy. I had never seen a comedy before that also had a sort of whodunit as an arc over the course of the season, and who's got the pin, who's got the watch? We keep all of that stuff up in the air until the last moment of our finale. 
How do you think Black Monday sits in comparison to other Wall Street stories audiences have seen before?
I think that the makeup of our cast, and the diversity that we're dealing with, and this Bad News Bears group of traders — these are all things that I haven't seen in this arena before. We're using this particular group of characters, who wouldn't have existed in the way that they exist in this show — all together, under one roof, in a trading house on Wall Street — to talk about a lot of things. They're trying to carve their way in this world that was really not open to them. Usually the characters in this kind of show are world-beaters, they're on top of it and they're crushing everything. These guys are just trying to hang on.
This interview has been edited and condensed for clarity.