How 'Black Monday' Mines '80s Greed for Meta Comedy

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As you watch Black Monday, the new Showtime series starring Don Cheadle, you'll probably start to realize something is, well, a little off. For me, that was when two Ken Marinos showed up playing the "Lehman brothers," Lenny and Larry. Yes, Lehman Brothers is the name of a famously defunct Wall Street firm. No, "Lenny and Larry Lehman" never existed.

The show, from Jordan Cahan and Happy Endings creator David Caspe, tracks a misfit group of traders at the Jammer Group, an upstart company led by Cheadle's slick Maurice (Mo) Monroe, in the lead-up to the 1987 stock-market crash. It dabbles in both lunacy and knowing commentary on Wall Street (and, for that matter, Wall Street) tropes, and it's also a mystery with a ticking clock that gives it a sense of urgency. That's because the pilot episode -- directed by executive producers Seth Rogen and Evan Goldberg, and made available ahead of the series' official January 20 premiere date -- opens with a body falling onto a red stretch limo parked outside the New York Stock Exchange on October 19, 1987 (the day of the crash), before flashing back exactly a year.

We learn that Mo, along with his Jammer crew, notably Dawn (Regina Hall) and Keith (Paul Scheer), hatch a devious plan to take over the fictional Georgina Jeans, first by rooking the Lehman brothers into selling low (they think it's high) and subsequently targeting a newbie named Blair Pfaff (Andrew Rannells). Caspe and Cahan talked to Thrillist about the show's meta moments and what to expect from Season 1.

What interested you in doing a comedy about the 1987 stock-market crash?
David Caspe:
My father was a commodities trader in Chicago in the '80s and '90s. Although Chicago trading is different than New York, it's sort of a similar culture. He used to tell me crazy stories and, of course, we grew up loving the movie Wall Street and had read a bunch of books about it. The '08 crash got us thinking about crashes in general. In the same way the financial market repeats itself, history repeats itself too. It just felt like a way to do a period piece that would inevitably be relevant still. And sadly it's happening all over again now. But what also really attracted us to it was the craziness and the decadence, and the wild personalities of '80s Wall Street inherently struck us as funny or at least an area for comedy. The world of Wall Street itself lent the story such big stakes. You can lose all your money in a day or you can make more money than you've ever had in a day. A lot of people literally lost so much they killed themselves. The stakes are truly life and death or boom and bust to a level that felt like it lent itself to the dramatic turns and cliffhangers and plotting turns that we were interested in doing. We had this goal of seeing if you could do a comedy with a lot of jokes that still had the plot twists and turns of a bingeable drama, which we felt like we hadn't seen there. It was perfect that this very wild very funny world had the crazy stakes that would let us do that plotting.

Thrillist: How did you decide on the show's structure?
Jordan Cahan:
I think it felt exciting to us to start with the body fall and keep that a mystery. For us, the fun of it was really that the tie pin and the watch are the musical chairs of death. They are these two pieces that get passed around through the show and while the characters themselves may want them we as the audience are like, "Oh no, you don't want them because we've seen ahead and whoever lands on both of them is probably going to die." So for us to do that kind of necessitated this structure of building up to the crash. I think the other issue was the crash itself has always been one of those "history's mysteries" as to how it happened. It was also kind of a fun challenge because normally on a show you're not really worried about how much time has passed, what season is it, where are the characters in their relationships, what happened in the last month. That was a particular challenge for this show but I think it was a way to have a lot more character movements in building a season and having these characters really change and grow over the course of the season. It feels like you can earn that a lot better when you are arcing over a whole year.

The show follows Maurice Monroe and his ragtag crew. What inspired these characters?
Along the lines of '80s movies, we wanted to do a real underdog story. It felt like, what better underdogs or a more interesting story to tell than all the people who couldn't get hired at the big firms back [when it] was 99% white, old, blue blood money. So, it just felt interesting to be like, what were the people that couldn't get hired there doing, [when they were] inevitably as talented or more talented than many of the people working at those firms. So if someone were to gather those people up a la Bad News Bears or Major League or Revenge of the Nerds or something like that, what would that group look like? The women and people of color. It just seemed like a really interesting story and also maybe one that hadn't been told in that setting. There have been a lot of Wall Street movies about white rich Wall Street traders. I don't think many people really want to see another one of those. Maybe they do. It just felt like a fresher take on the world.

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There is a meta quality to some of the humor. Why did you want, in the context of the show, to comment on these ideas of Wall Street that we have?
I think for us part of the fun of this show is we try to make the show authentic but at the same time we aren't afraid to look back at it with a wink. Our characters are slightly prescient about the fact that some of the social mores of the '80s are now, when we look back... we are slightly horrified. And at the same time, there is some amazing stuff about the '80s, like the music and the art and the fashion, that we want to laud. So, because we're not a drama, it weirdly gave us this fun grab bag [where] we could take the stuff we love and we could poke loving fun at the stuff that feels outdated now.

How did you come up with the idea of having literal Lehman brothers?
It was '08 and Lehman Brothers had just gone under. We knew if we were going to tell the story of all the people that couldn't get hired at the top firms, we needed one of the top firms represented. It somehow came into our heads that it would be funny if the Lehman brothers were twins in the villain '80s movie trope of evil twins. Then we also thought it would be a way the show could kind of feel relevant because it's referencing this firm that everyone knows eventually will go under, but seeing them kind of in their heyday. It's not obviously based on any actual Lehman brothers or any two people running the firm. We kind of played with the form as much as we could in homages to tropes from the '80s that we liked, like evil twin brothers and some of the evil characters having eye patches. There's a joke in the third episode -- actually a joke that a reviewer has said he doesn't like -- where Horatio Sanz's character mistakes what Duck Hunt is called. That is a way where it is playing with the form or alluding to those '80s jokes where everyone used to say "Mike Hunt." And obviously in certain cases it's not going to land for people and that's maybe a very subtle one. That was such a dumb structure for a joke back then that it just felt like, why not have one of our dumb characters making a dumb joke that is also in the structure of a dumb '80s joke felt like a funny comment on that and on joke structure and things like that. Some of those things are maybe too subtle to come through. There's a bunch of that stuff throughout the show, which would be termed meta.

How far did you guys did into research to lend that side of the show a verisimilitude?
We did a lot of reading. We read Barbarians at the Gate, we read The Predator's Ball, we read Den of Thieves. There's a documentary on Paul Tudor Jones that's really interesting called Trader. We did a lot of research on the era, but at the same time we're a comedy and God knows we're not economists or anything near. So, for us, it was important to make it simple enough and fun enough and hopefully enjoyable enough and exciting enough for the audience that they could follow along and not get bogged down in stuff that feels like it would be closer to drama territory or documentary territory. And I think when you talk about the Lehman brothers, that's kind of a good example of how this show exists about a foot off the ground. We really want you to fall in love with the characters and be rooted in their relationships and their struggles, but at the same time, when it comes to the economics of it all, we did all the research and then, I always say, we threw it all away. To me, the most interesting stuff in those books was always insane stories and the insane tales of excess and greed of these characters and I think that's what we stole more from. The part of the conception of the show that got us excited was there was no definitive answer for why the market crashed. So there's a few theories and we incorporate some of them into the finale, but it felt fun to just do a fuck-all take on what could have happened. I think for us the Maurice Monroe-Blair Pfaff smashing into each other with the coke on the floor is the big bang of what will happen one year earlier and crash and tank the market.

You set up this year-long time frame. Are you giving yourself a season to get to the crash? Will you have an answer to who that body is? Or are you setting up a multi-season arc leading up to the crash?
As a super mystery nerd, I always find it a little bit unsatisfying if a question that's raised -- unless it's the bedrock of the series -- isn't answered by the end of the series. It feels like a promise that you want to keep. So we intend to keep that promise both ways. We're excited for people to check it out. I would say ultimately the clock will click down to Black Monday for the finale.

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There was a huge debate when The Wolf of Wall Street came out about whether it's condemning or glorifying its subject. How did you approach these questions of how to portray the excess?
Cahan: We tried to be very thoughtful. One of the cons of the era is that it's this very bro, aggressively male toxicity. For us, we felt really stuck on a lot of these things of how do we show that without being a party to it. Part of that was obviously going with a diverse firm and part of that was trying to be really true to Dawn's story and tell that. At the same time there are little things, like there is language that's deeply offensive and outdated, that we were very specific about what characters were allowed to use and when. We felt like an interesting way to explore the misogyny of the era was to give it to Paul Scheer's character, Keith, because it's clearly a cover for him for what his true sexuality is. We were like, Oh, that's an interesting way to show that in a way that feels sensitive to it but at the same time straddles the authenticity of the era. We really took it on a case-by-case basis. For example, there are billions of stories of these guys going to strip clubs and dealing with prostitutes and stuff, and for us it was important that, while they can allude to those adventures, we never wanted to... Dave you want to take over, because you have a really nice thought on this?

Caspe: When you go to a strip club in a show, especially on cable, you're inherently showing female nudity. And yet even if we are doing a satire, it feels a little bit icky that we are contributing. It's very much a look back at the era in a way that a lot of people were unaware of at the time because those were just the social mores of the time. But, yeah, we tried to be really sensitive about that. Just because we're a cable show doesn't mean we should be pushing these buttons. At the same time, we felt like some of the villain characters could embrace what was more of the norm there because it felt like, okay, they will either get their comeuppance or they won't but at least we are putting it in the mouth of someone that we know is morally corrupt or morally bankrupt. It's an interesting fine line. The show is obviously a satire. It's very hard to say "isn't horrible that all these men objectified these women by spending their time in strip clubs?" if we show those strip clubs and ask a bunch of actresses to have to dance around with no clothes, we are objectifying them by putting them in the show naked. We decided to never go to the strip club, just to hear about it, because if you hear about it then we are making our comment without actually having to have ourselves have women be objectified on the show.

I've seen three episodes and we're still 300-plus days until the crash. Was it a challenge to space out the time jumps?
It was difficult, definitely, to do a full year in 10 episodes, not to mention some of the things we are trying to do from a character-arc standpoint for all the characters. That was definitely a challenge in figuring out How many months do we have to jump ahead? How many months can we jump ahead? Where are the characters if you jump that far? Is it jarring or will people will go with you on it? It was definitely difficult because we are trying to take characters from A to B. That's kind of hard to do and I don't know if we did it. Hopefully we tried.

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Esther Zuckerman is a senior entertainment writer at Thrillist. Follow her on Twitter @ezwrites.