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‘Black Monday’: Getting Laughs From the Worst 1-Day Market Crash Ever

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Tragedy plus time equals comedy. The veracity of that familiar calculation is what Showtime is banking on with a new comedy series satirizing the horrific market crash of Oct. 19, 1987, when the Dow Jones industrial average suffered the biggest single-day plunge in Wall Street history.

But forget history if you watch the 10-episode “Black Monday,” premiering Sunday at 10 p.m. A funny, fictionalized take on what “really” caused the crash, it focuses on a made-up Wall Street firm of oddball outsider traders in 1986-’87. Don Cheadle (“House of Lies”) plays The Jammer Group’s high-octane owner.

In an interview, the series’ creators David Caspe (“Happy Endings”), 40, and Jordan Cahan, 41, told ThinkAdvisor why they decided to poke fun at the financial services industry.

Seth Rogen (“Knocked Up”) and producing partner Evan Goldberg (“Superbad”) are executive-producing the show and directed its pilot episode.

“This is a funny fever-dream look at the business,” Caspe says. “It shouldn’t be watched for accuracy. We invented rules to help the stories.”

The far-fetched premise: A group of underdog traders take on the white-male old-boys club of Wall Street and crash the financial system.

Cheadle’s character is head of an inclusive Wall Street trading firm packed with folks of diverse races and sexuality. During the 1980s, most would never have been hired as traders, insist Caspe and Cahan, who are Caucasian.

At Jammer, a black woman holds the position of head trader, played by Regina Hall (“Girls’ Trip”). Andrew Rannells (“Girls”) is a young, naïve trader; and Paul Scheer (“The League”) is a trader who’s eager to please.

Though the writers took liberties with history, Caspe first picked the brain of his dad, a former Chicago commodities trader. For one, he learned about the wily practice dubbed “The O’Hare Spread.” Caspe and Cahan turned it into “The LaGuardia Spread” for the New York-set series.

The show is laced with coarse language, and visible cocaine consumption is SOP.

ThinkAdvisor recently talked with Caspe and Cahan, speaking by phone from Los Angeles, where they were deep into editing  “Black Monday’s” fifth episode.

Here are excerpts of our conversation:

THINKADVISOR: The real-life Black Monday was a dreadful day on Wall Street, when the Dow plummeted 22%. But you’ve made comedy out of it. What was your aim creatively?

DAVID CASPE: It’s a funny, hyper-color fever dream of Wall Street rather than a documentary. I feel that in some ways, people in financial services would prefer to watch the comedy version, where we just made up everything rather than trying to make it accurate.

JORDAN CAHAN: We’re comedy first. Beyond that, we’re trying to satirize [1980s Wall Street] culture and hold up a bit of a mirror to the world now.

But are there any parallels between the series and history? Actual Black Monday holds the title of the worst single-day market drop ever.

CAHAN: To this day, people are still puzzled and theorizing about what caused that crash. We felt it was a really fun opportunity for comedy and to fill in the blanks of history by creating our own little insane world of how the crash happened. It’s historical fiction.

I’m not asking to reveal anything specific, but what are you saying caused the crash? [Spoiler Alert!]

CASPE: It has something to do with [trader] Blair’s [Rannells] algorithm. There’s been a lot of speculation that trading programs had something to do with [the real Black Monday] — that when one of them triggered sell orders, that triggered a waterfall and then panic and accelerated selling. Our reason [for the crash] is a bit like that but a little more “on purpose.”

Left to right: David Caspe, Jordan Cahan and Seth Rogen behind the scenes of "Black Monday." (Photo: Erin Simkin/Showtime) Left to right: David Caspe, Jordan Cahan and Seth Rogen behind the scenes of “Black Monday.” (Photo: Erin Simkin/Showtime)

What inspired you to create the series?

CASPE: I’ll sound incredibly stupid trying to talk about finance because I don’t know much about it — but my father worked as a soybean trader in Chicago and would always tell me crazy stories about Wall Street and trading in general. The ones from the 1980s were particularly funny but also incredibly heartbreaking. It all seemed ripe for a comedy [about that period] with a lot of jokes about the ridiculousness of the ‘80s, the excesses, and the wild characters you’d find in the world of trading.

What about plot?

CASPE: There was also the crazy high stakes where people could lose everything in a day or a minute and literally jump to their deaths. It was an odd combination of things that are really funny but also kind of terrifying.

What’s one of the stories your dad told you?

CASPE: It was about “The O’Hare Spread”: If a trader was down to his last dime, he’d take a huge position on margin. Then he’d go to O’Hare Airport and from there, call to check on the trade. If it was a winner, he’d come back a hero. If it was a loser and he lost everything, he’d get on a plane and disappear forever, leaving his family behind. That was a real thing my father told me about.

Did you put it in the show?

CASPE: Definitely. We just transported it to New York and renamed it “The LaGuardia Spread.”

Did you ever aspire to work in financial services?

CASPE: I admire it quite a bit, but I’m very much the other brain [right-brain dominated]. I have the opposite of the trading brain. Trading requires so much math and that kind of financial stuff, which is probably not the best thing for a comedy writer [to work with].

Please describe “Mo,” Don Cheadle’s character.

CASPE: He’s head of The Jammer Group, the No. 11 trading firm on Wall Street in 1986-’87.  He’s very ambitious, erratic and prides himself on the fact that his company employs people who couldn’t get hired anywhere else [ostensibly, because of discrimination]. The people that make up his firm are of all races, creeds, sexuality — those who had no place to go in the ’80s.

In the pilot episode, Mo says that his “favorite thing is money,” and his “second-favorite thing is doing coke.” That seems to describe him in a nutshell.

CASPE: It’s all meant to be a joke.

Regina Hall plays ”Dawn,” a black woman head trader. Quite unusual in the 1980s.

CASPE: The whole show is about people who couldn’t get hired at the blue-blood white-male firms back then because of prejudice. They were people of color and women who were just as talented as those men. The series is about underdog traders grouping together and trying to take down the establishment. It’s the story of how these people, because of the times and the business, couldn’t get hired or rise up at some of the larger, more established firms — still [happening] today probably.

Therefore, the series always needed to be cast with a mix of people of color?

CASPE: Yes. We wanted characters that didn’t show up in traditional Wall Street movies of the ’80s.

There’s routine cocaine use and raucous goings-on in the The Jammer Group’s office. Were you inspired by “The Wolf of Wall Street”?

CASPE: Shockingly, this project has been around since before “Wolf of Wall Street,” the movie, and “Wall Street 2 [“Money Never Sleeps”]. We weren’t even aware of the book “Wolf of Wall Street.” But that movie was about an off-Wall Street pump-and-dump chop shop. Our show is about actual trading on the floor — obviously people doing illegal stuff, but they’re doing an actual company takeover.

Were you influenced by the first “Wall Street” movie (1987), then?

CASPE: Definitely. The excesses, the glamour, the greed, the ambition, the gamesmanship, the competition. It stuck in our brains from when we were kids.

A pair of twins in the show are called the “Leighman Brothers,” pronounced “LAY-men,” like the real former firm. Seems as if you’re mocking Lehman Bros. Did you have any problems using that name?

CASPE: Yes, which is why we changed [the spelling]. But those characters aren’t based on any actual people that worked at Lehman Bros. or anyone from the Lehman family. We thought it was a funny joke to use a name that sounded like an actual [firm] name and to make the characters evil twin brothers, which was a very ’80s trope.

Cheadle’s “Mo” has a robot butler named “Kyle.” What prompted you to include that?

CASPE: It was inspired by a few ’80s movies, like “Wall Street” and “Rocky III.” We thought it was a very ’80s thing to have a robot butler.

How does Kyle help Mo?

CAHAN: He generally buttles.

But of course.

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