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'Black Monday' is not a Great Investment
January 20, 2019  | By David Hinckley

Thirty-one years should clear the statute of limitations for making a comedy about a devastating stock market crash.

Black Monday, a new comedy that debuts at 10 p.m. ET Sunday on Showtime, hooks its jokes onto the Wall Street plunge of October 1987, still the biggest single-day drop in stock market history.

With Don Cheadle, Andrew Rannells, and Regina Hall in the lead roles, Black Monday is well-stocked with talent. It’s only missing one thing, really, which is being funny.

Produced by Seth Rogen and Evan Goldberg, Black Monday nominally serves up a wild-and-crazy satiric explanation for what might have caused that day’s crash.

Cheadle plays Maurice Monroe, a stock hustler who rose from nowhere to run a mid-level rogue Wall Street firm. He has done well enough to be chauffeured in a limo that might be a Lamborghini or might be a DeLorean. He inhales enough cocaine to keep three cartels in business.

He embodies and triples every insane excess ever attributed to any rich, arrogant Wall Street whiz kid.

That sounds like it should be funny, which makes it a little surprising how soon it feels more like tiresome.

Rannells plays Blair Pfaff, a recent college graduate who has developed an algorithm for stock trading. Today, every 4-year-old with a Sesame Street app could do that. In 1987 it was considered enticingly futuristic, and Blair is hotly pursued by giants of The Street like Lehman Brothers and Morgan Stanley.

An encounter with Monroe, however, sends Blair down an entirely different path. His fate is batted back and forth like a volleyball by major players until he gets spiked into Monroe’s obsessive scheme to take control of Georgina Jeans.

While that’s playing out, Hall brings a third party into the center of the action. Wall Street was, and largely remains, a boys’ club. Hall’s Dawn Darcy is having none of that, though she isn’t above playing the "Girl Card" when necessary.

There’s an Ocean’s Eleven element to Black Monday. A long con moves along quietly behind several more obvious short cons, and while they’re sometimes more complicated than interesting, they do move the story along.  

Between whole scenes that are mostly excuses for Cheadle to deliver manic comic monologues, often quite amusing in themselves, the show does move toward the endpoint given away by the show’s title: There will still be a Black Monday, on which things will not end well for some people.

Inherent in the buildup to Black Monday, however, is the unavoidable fact that we feel little or no sympathy for almost anyone we’ve met. The game set in motion by Monroe, Blair, and Dawn doesn’t seem to have many consequences beyond denting the filthy riches of people who are smug, obnoxious and oblivious.

Yes, it’s satire, and yes, we get clever twists here and there as Rogen and Goldberg imagine the weirdest circumstances that could possibly have triggered Black Monday.

It’s a shot worth taking. It just ends up a little too cartoonish, and not quite clever enough.

Black Monday gets a sell order.

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