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Black Monday's Producers Explain Why [SPOILER] Confessed and Went to Prison in Season 2 Finale

Plus: what might be in store for a potential Season 3

Malcolm Venable

[Warnging: This post contains major spoilers about Season 2 of Black Monday.] 

If you stuck with the joyously demented carnival that is Showtime's Black Monday for all of Season 2, you know it took bonkers to new heights, even for a show that was pretty bonkers to begin with. By the time it was done, we'd seen a half-dead man sing a song through a computer; an epic shoot-out that looked like something out of Rambo; the precursor to the modern-day dick pic via a Xerox'd willy; and a whimsical musical number inside a white-collar prison that celebrated the joys of wealthy white privilege. 

Yes, the jokes, set pieces, and gags in Season 2 of Black Monday were a lot, in the gleeful, "I can't believe they just did that" way that makes the enjoyably absurdist romp unlike anything else on TV. Season 2 also juggled a dizzying number of overlapping storylines involving financial jargon and backstabbing schemes, with Mo (Don Cheadle), Dawn (Regina Hall), Blair (Andrew Rannells), Tiff Georgina (Casey Wilson) and Keith (Paul Scheer) tangled up in crisscrossing tales of revenge and oneupmanship. At the conclusion of its 10 episodes, we'd seen Mo try to do something right for a change, the once-innocent Blair turn dark, Keith cozy up to the Lehmann brothers, and Dawn land in prison after confessing that she was the one who engineered the Black Monday crash that kickstarted the series. Even if the intricacies of every story turn became a little head-scratching at times, the overall movements made Season 2 like a wild, intoxicating ping-pong match that ultimately finished with Dawn in the clink and Mo back at square one. 

Why did Dawn tell on herself? And what might a Season 3 look like if the Showtime gods smile on us? Executive producers Jordan Cahan and David Caspe talked with TV Guide about how the madcap season came to be, some of their favorite moments, and what they're thinking about next. 

(This interview has been edited and condensed.)

There was so much happening inside this season; how'd you map out what you wanted to have happen? 
Cahan: Well, that's funny, because I was thinking before this call, as comedy people, it's rare that we get to go story first. Usually, it's like, what jokes, what is a funny set piece. But it's good to go story first, and that was what so fun about the season. We really did talk about where we wanted the characters to end up. What is the final frame of each character? Where are they? And then the real question was, how do we get them there in a way where we're juggling all the characters but where you can't get so cleanly ahead. So that it feels like a drama where the journey is exciting and unexpected, but hopefully at the end, it all feels like it makes sense. We're not used to doing that for comedy. I think the fun of that was looking at a board and bringing out where the characters' peaks and valleys were and how we could get them to all interact. 
David Caspe: I think the end game that we were excited about was Regina [Dawn]. The room as a whole got to a place where they're like, "Okay, the most interesting thing is that a Black woman is responsible for [Black Monday] which was actually a brilliant trade, but also something very illegal. There's such an interesting dichotomy of wanting the credit or something that also would take you down, but being so frustrated over the course of the season that you're not getting the credit you deserve, that in the end, she basically turned herself in to get the credit more than anything. We had where everyone begins and we had where Regina ends and we had to figure everything else out.

Black Monday Wasn't Conceived with Black Leads, but It's All the Better for It

One of the things that stood out to me was the feminist theme of the season. You have Dawn in charge of a mostly female firm at the start, and then this subplot where Wayne (Horatio Sanz) is this incel character determined to punish women. Was Season 2 intended to be an overtly feminist statement? 
: I think every character we have is, for lack of a better word, not a straight white man. Looking at how they have to navigate today through the lens of the '80s is really been what the show is about a little bit and I think inevitably women are a big part of that. The Just for Men thing from Wayne was very much about a lot of men's reactions to like, the female Ghostbusters and stuff like that just felt insanely ridiculous to us. It just felt natural that if we've got this woman who was the mastermind behind Black Monday, she would break the glass ceiling and start this all-female firm, but inevitably you're gonna have one of these sort of incel type-men who reacts in this misogynist way. You see it constantly now, as a reaction to the Time's Up movement. They always frame it as like, "I'm a men's rights activist," which, you know, straight white men don't need activists. They've done just fine. So a lot of the story is, "How did we get to the end game?" We really wanted all the characters and stories to be very interconnected. 

You've talked before about how your writers' room is mostly people of color and/or women -- and you had that in place before the new push for more inclusivity behind the scenes. Do you feel like you were ahead of the curve there? 
Saying it's a mandate is sh---y. For us, it's always been our absolute desire to have the most diverse rooms as humanly possible. I've never worked any other way and I won't. Yes, it happens to fit this show hand in glove, but I just think it's the way shows should be made. 
Caspe: And it's also selfish, frankly, in that you get a better show that way...the more perspectives you get and voices you get in the room [you get] more variety of hilarious jokes and experiences that inspire storylines. 
Cahan: I can think of two or three storylines that I would be really afraid to touch, that would be like third rails, and the room was so encouraging going in that direction. Ultimately, you want them to lead you. Not only did it end up educating me, but I think it makes the show richer. Dawn borrowing from what is essentially the United Negro College Fund. Stories like that where it's like "Do we really want to do this?" and then having the room get so excited, to put that character in such a difficult moral position. 
Caspe: And the story itself is just not one that I would think of. The relationship between Dawn and her mother is informed by Black women in the room. I wouldn't have come up with the nuanced, intelligent version; I would come up with like, an outsider looking in assumption of it rather than something that felt authentic. A lot of [Blair's] story was inspired by people that went through similar things of what it means to be gay in a religion that doesn't accept it. That's not my story to tell; I also don't know it, because I haven't been inside it.

Let's talk about the brilliant song "White Collar," Keith sings in Episode 5. How'd that come to be? 
 We knew we wanted to [take on] Club Fed because it was such an '80s anomaly. And it was so weirdly written about in the '90s as like, "Can you believe this happened?" It felt almost like a Simpsons-style step out where all of a sudden you're seeing things...it felt like a fun, silver bullet way to describe what you're seeing in these prisons but in the same way but a silly, fun thing that stretches the limits of credibility where we didn't know if we could pull it off and still feel like you're in the real world. 
Caspe: It was very inspired by the Simpsons musical numbers. 
Cahan: It was "See My Vest" from The Simpsons. It was Maison Derrière Simpsons. We probably pulled the rubber band back as far as we could with that one.

In that vein, the visual gags and set pieces in Season 2 went to a new level -- the bank shootout, in Episode 3  ("The Idiot Inside") for example, the most over-the-top. What were your favorites of the season?
: I would say the things that got me excited are on two ends of the spectrum. And I'm sure Dave's would be different but on one end, the bank is as ambitious anything we've ever done. I mean, the idea of not just making it a little music video or alluding to it, but actually playing it, and really destroying that bank digitally and physically, having to do a lot of practical effects and plotting that whole thing out. We had never done an episode that didn't have a B-story. So we have never done an episode that didn't cut away to the other characters. So it was very much like writing a play, but a play that could get explosive very quickly. I can't tell you how much fun it was for somebody who grew up with '80s action movies and loves them so dearly, to be able to do that. And then weirdly, on the complete other side of that, I would say the very next episode, which was on purpose, was the country club episode. We wanted it to feel zany and goofy, almost like a Three's Company episode in the same way that our bank episode feels like a Miami Vice or something like that. The country club episode deals with race and class and sexuality and religion; we really wanted that to feel like a farce. And I think I think we got really lucky with our writers, directors. I really love the way the show can go from one complete extreme to the other.

It sure seems like Mo is full-on in love with Dawn, but he just can't seem to get over himself. What's up with their dynamic and why he's so reluctant to be vulnerable with her?
I think this season he was a victim of circumstance, which was like sort of the most tragic [part]. Usually, in the past it's been his own ego and his own lack of vulnerability that has [messed things] up with her, you know, I think this season, he was getting on that plane. He was going to disappear forever. Now granted, he had just completely f---ed her over, but he was completely f---ed over by her Black Monday. She did steal his entire company and basically took all his money. So he was pissed. And he did his one last piece of revenge to screw up her bank deal. And then he got on that plane and was leaving. When the FBI caught up to him, they forced him back to help them find who was responsible for Black Monday. And in that respect, he was trying to keep Dawn out of it, and he was genuinely trying to steer them towards Blair and saved Dawn. He just kind of wasn't able to. But he really was trying to do the right thing by her. I also think we were trying to look at [how] there's still sexism within races or cultures. When you flashback to him, he genuinely looked at it as like, I'm the one who got the seed money, I'm the one who got on the [Wall Street] floor. Like I think it never occurred to him that Dawn would have been his partner. Mo has some sexism [about him] too. 

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But, he's willing to take the rap for her. I read that as a sign of his deep abiding love for her, and I reading that wrong? 
No, you got that. He literally says, "I'm going to be the tragic hero." He's trying to display that he's changed. At the end he runs into Keith and Keith is basically telling him "You are going to go away for life." And Mo continues on. He goes to the FBI and he confesses, he's willing to do the sacrificial thing. 

Where are you thinking about for Season 3, if you get renewed?
Maybe the '90s. It's almost '89 by the end of Season 2, so there's something interesting about 1990, or even jumping ahead.
I'm really excited by where the four chess pieces are. We really wanted to position them in these exciting places. Season 2 starts with Blair making a deal with Tiff and they have this understanding, and they're going to help each other. And by the end of the season, you can see she's kind of terrified of him, and how far he'll go for power. And we get a glimpse into his background and know that when his back is against the wall, he's not afraid to push back all the way to protect himself. Now I'm like, "Oh, God how bad is this going to get?" I think for Mo, it hinges on a little be careful what you wish for. Now he's inadvertently got the immunity he's always wanted. All of his old transgressions are wiped away. He's a new man. He can start again clean, but the question is at what cost? For Dawn, we were very careful to not mention how long she'd been put away or how deep of trouble she's in. But clearly it's a very serious crime. We've painted ourselves into a corner of how could that possibly work? And then for Keith it's another be careful what you wish for [situation]. He's finally found someone who really appreciates him. But there's a bit of a Single White Female relationship. I feel like if Season 1, we painted ourselves into a corner, I think Season 2, it would be even more fun to watch how these four people, who seem to not be able to get out of each other's way, and their lives would continue.

Last question is, in the final moments, we see Lenny, that poor twin who's just come back from the brink of death, being attacked by a wolf after being left in the woods by his brother. The guy can't catch a break. Is he dead, or just in bad shape again?
I think it would be the same thing as Season 1. So if he died again at the end of Season 2, if you're a betting man I would bet on Lenny's triumphant return at some point in Season 3 if we get it, probably even more mangled than he was at the end of Season 1. In classic '80s villain [style].  

Paul Scheer, Regina Hall, Don Cheadle, Black Monday

Paul Scheer, Regina Hall, Don Cheadle, Black Monday


Black Monday concluded Season 2 July 19; past episodes are on Showtime.