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Showtime's ‘Black Monday’ takes an absurdist yet pointed look at 1980s Wall Street

Showtime's ‘Black Monday’ takes an absurdist yet pointed look at 1980s Wall Street
Andrew Rannells, from left, Don Cheadle and Regina Hall star in "Black Monday," a new comedy from the makers of "Happy Endings" that takes an absurdist yet still pointed look back to the time of the 1987 stock market crash. (Kirk McKoy / Los Angeles Times)

On an elaborate set designed as a garishly authentic 1980s Manhattan hotel room, Regina Hall, Andrew Rannells and a mustache-bearing Don Cheadle gather around a table, trading barbs with such quickfire pace you’d never guess this was their fourth or fifth run through the scene.

Rannells portrays Blair, a smart but very green Wall Street trader of the era — think slicked-back hair, round-rimmed glasses and pleated suits — who is being manipulated on either side by his coworkers played by Cheadle and Hall, whose Maurice (“Mo”) and Dawn run the rebellious, take-no-prisoners investment firm the Jammer Group.

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Showrunners David Caspe and Jordan Cahan look on in the next room, as quips and alternate lines rise and fall with delicate timing. A confession from Rannells’ character about his nose whistling leads Cheadle’s Mo to wonder if he left a tea kettle on, while Hall as Dawn jabs him about living alone in a luxury hotel the past 15 years instead of sharing his life with a partner. “Sharing is oversharing,” he counters, a sharp defense that didn’t exist in any of the prior takes.

As the line lands, director Reginald Hudlin raises his arms in front of the monitor as if signaling a touchdown. Cut is called, and a laughing Hudlin turns and says, “That’s the show, right there.”

Welcome to “Black Monday,” a new Showtime comedy series that imagines the stock market crash of 1987 as the result of a rogue brokerage firm aiming to outfox the older (and whiter) Wall Street establishment. It’s a milieu seeped with the greed and decadence that inspired Oliver Stone’s “Wall Street” and, more recently, “The Wolf of Wall Street” and “The Big Short.” But given that the creators of the series (premiering Sunday) are known for the cutting, cultishly admired network comedies “Happy Endings” and “Marry Me,” the goals for this series are a bit different.

Don Cheadle as Maurice "Mo" Monroe in "Black Monday."
Don Cheadle as Maurice "Mo" Monroe in "Black Monday." (Erin Simkin / Showtime)

“We describe [the perspective] as ‘three feet off the ground,’ ” Cahan says between takes. “It’s just impossible to top what’s happening now so we have to kind of put a fun house mirror on what was happening then.”

Consequently, Cheadle’s Maurice occupies an outsized world of Wall Street excess to rival anything imagined by Gordon Gekko. Between snorting cocaine off a Nintendo game system pistol and getting the occasional high-five from his robot butler, he’s chauffeured around New York in a candy-colored Lamborghini limousine. That’s when Maurice isn’t taking meetings with founders of the rival firm Lehman Brothers, which for the purposes of “Black Monday” are represented by a pair of evil, tandem bicycle-riding twins (both gamely played by “Marry Me” star Ken Marino).

Plus, not unlike “Happy Endings,” the back-and-forth dialogue keeps a heavy foot on the throttle. “The pace is pretty fast,” Caspe says with a shrug. “Everyone is on cocaine.”

When told during a later phone call that “Black Monday” may have set a new onscreen record in terms of a fake cocaine budget, Cheadle can’t resist flexing a comedic timing that’s goes hidden in his dramatic work. “Who said it was fake?”

Andrew Ranells and Regina Hall in Showtime's "Black Monday."
Andrew Ranells and Regina Hall in Showtime's "Black Monday." (Erin Simkin / Showtime)

So it’s not the sort of ripped-from-the-headlines social examinations you might find in the reporting of Michael Lewis or more recent investigations of an emboldened financial industry surrounding the 2008 crash and beyond. But for all the jokes about over-the-top behavior alongside the show’s central mystery leading up to the stock market crash, reality hasn’t been pushed entirely out of frame.

“I think it’s the only way comedy really works; it’s got to be pushing back at something that’s truthful and real and has some gravitas, or else you’re just kind of freewheeling out there,” says Cheadle. “And in this particular instance, we’re dealing with things that are still current. These big fluctuations and terror that we’re seeing in the marketplace and a lot of prognosticators saying they think that we’re headed for another situation like we had before — yeah, it is serious stuff that we’re playing with, but that’s also the reason why it’s very funny.”

“I think you get to explore a world in a different way,” adds comic and podcaster Paul Scheer, who plays a trader at the Jammer Group caught in a moral and financial tailspin. “I think David and Jordan are really good at being able to comment on things that are of the ‘80s and not just be like, ‘Look at this, a Rubik’s Cube.’ ”

“That’s a lot of fun of it too, skewering a lot of the cultural references from the past — from music, fashion, art, all of it gets kind of thrown in,” Cheadle says. “And what do these things mean now, and how different are we and how similar we? A lot of the jokes and the popular culture that we’re talking about is so much more shocking than anything that you’d be allowed to do now.”

“It’s just impossible to top what’s happening now so we have to kind of put a fun house mirror on what was happening then.”


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While the Wall Street of the 1980s was built upon absurd levels of decadence (stories of parties thrown by junk bond trader Michael Milken made the rounds on set), “Black Monday,” which is executive produced by Seth Rogen and Evan Goldberg, also has an eye on the social progress — or lack thereof — since that era. In trying to secure her own fortune, Hall’s Dawn reckons with the glass ceiling as well as the casual racism of the ‘80s that still happens today. And while the show grounds its setting in gleeful references to Billy Ocean, “Wall Street” and “Working Girl,” one passing joke calls out what was, in its time, a triumphant scene in 1984’s “Revenge of the Nerds” that actually was, in uncomfortable hindsight, rape.

“The sort of bad line we throw around is like, ‘Look how far we haven’t come,’ ” Caspe says. “And so the show is sort of a way to satirize the ‘80s but also satirize current culture, which when you look at how crazy it was 30 years ago . . . you really more have the feeling of wow, we really haven’t come that far.”

“Now look, we are a comedy first,” Caspe later clarifies. “I wouldn’t want to be planting our flag as if we’re doing some great social service to the world, but it was all sort of right there.”

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Regina Hall as Dawn in the second episode of the Wall Street satire "Black Monday."
Regina Hall as Dawn in the second episode of the Wall Street satire "Black Monday." (Erin Simkin / SHOWTIME)

For all of “Black Monday’s” exaggerated portrayals of ‘80s finance, that world lies close to Caspe’s heart. His father was a commodities trader in Chicago, and while that was a different world from the bare-knuckle business deals of Wall Street, his “hilarious and terrifying” stories inspired Caspe to explore that high-stakes world for a television series. With the festive lunchtime backdrop of a live mariachi band hired to commemorate the last day of shooting, Caspe describes “the O’Hare Spread,” which was a last-ditch maneuver for a trader who was, in poker terms, down to the felt.

“You would take a huge position on margin — which means you would take a huge loan — and make a gigantic bet,” Caspe says. “And then they would go to O’Hare Airport and call the floor and find out if it worked or if it didn’t work. And if it worked, they’d come home and be rich and everyone would be happy. And if it didn’t work, they would get on a plane and disappear. My dad legitimately knew guys with families and kids who he never saw again.”

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“The insanity of that, how dark it goes, that’s the granular piece for the weirdness of the show,” Cahan says.

“I think that energy kind of fuels each one of these characters on the show,” adds Scheer. “You start living this life where anything can change in a second, so people are making wildly inappropriate and insane choices.”

With the rise of Donald Trump bringing ‘80s opulence back to pop culture prominence while helping usher in another regulatory free-for-all on Wall Street, the stock market is again under scrutiny. It’s hard not to wonder if even a just-for-laughs immersion into the boom and bust financial world has resulted in a shift in perspective for the show’s creators.

“The world feels so divisive and amoral and angry,” Caspe says, “that there was something about the divisiveness and anger and amorality on Wall Street in the ‘80s in the show that kind of just felt like a subconscious or conscious reaction to how [terrible] everything feels right now.”

“In looking back at the ‘80s, it feels simpler compared to the ‘08 crash. The ‘08 crash was so much more global than Black Monday,” Caspe says. “I’m sure I’m wrong because I’m not an economist, but it makes the crash of ‘87 look quaint.”

Adds Cahan: “I’m thrilled the show is on right now, but, at the same time, what’s happening right now is so terrifying, it’s a little like staring at the sun.”

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