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Black Monday Review: Don Cheadle's New Comedy Goes All-In On Excess

Don Cheadle in Black Monday Showtime

The first ads for Showtime’s Black Monday didn’t exactly obfuscate what sort show its creators intended it to be. A half-hour dark comedy about greed and power and excess is not necessarily something new or particularly original in today’s television landscape, so the series smartly gave itself a couple of advantages. One of those advantages comes in form of Don Cheadle, who makes his return to television after spending the past few years playing with Tony Stark and the Avengers, and not too long after his previous Showtime series, House of Lies, ended in 2016. The other advantage Black Monday creators Jordan Cahan and David Caspe gave their story of Wall Street shenanigans is that of its period setting — late ’80s New York City — and a premise built around providing an answer to how the infamous stock market crash of October 19, 1987 (aka Black Monday) happened and who, exactly, was behind the event.

It’s a smart move. Showtime, Cahan and Caspe, and executive producers Seth Rogen and Evan Goldberg, are essentially hedging their bets that yet another series detailing the avarice of Wall Street will be of interest to viewers by turning the series into something of a gonzo, borderline slapstick comedy with a built-in real-life mystery at its center. Add to that a terrific cast that includes Regina Hall, Andrew Rannells, Paul Scheer, Ken Marino, Kurt Braunohler, and Kadeem Hardison, and there’s an attractive new series to watch in 2019. Provided, of course, you’re on board with its sense of humor and exuberant love of excess. 

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For a series that included as much cocaine as it did in its previews, it will come as no surprise that Black Monday doesn’t exactly play its cards close to its vest when it comes to the mystery of who caused Black Monday. The series begins with a title card explaining what Black Monday was (you know, for all those people who think 2002 is the beginning of time), which certainly helps set the stage for a red stretch Lamborghini limousine to arrive on the scene, weaving its way through the trash-strewn streets of NYC (again, this show’s all about excess). It’s a sharp vision of tacky overabundance, one that is punctuated (and punctured) by a body dropping through the roof of the limo from some great height. Though the identity of the jumper is obscured (again, Black Monday is really leaning into the concept of there being an element of mystery), there are a number of clues present: a tie pin, a watch, a suit. It could be Cheadle’s Maurice Monroe, or it could be Andrew Rannells’s Blair Pfaff. 

Don Cheadle and Andrew Rannells in Black Monday Showtime

Black Monday makes a smart turn at this point, as it quickly moves the question of who plummeted through the roof of a red Lambo limo on the back burner. It’s less important for the audience to wonder who the jumper was than for them to know why it matters that he jumped. To do that, the series has the difficult task of making the viewer care about a collection of very loud, very aggressive, completely unaccountable people for whom turning a profit is the only pleasure in life. In that regard, Black Monday’s depiction of Wall Street traders — those in Maurice’s shop and elsewhere — is one audiences have seen before. They’re not interested in building anything other their own personal wealth and, perhaps even more importantly, a sense of power over their peers. 

This is perhaps the biggest obstacle facing Black Monday: nearly two decades out from the arrival of Tony Soprano on television, how hungry are audiences for yet another depiction of men behaving badly and not only facing zero consequences for their actions, but being actively rewarded for them? That’s a tough question, and one need only look at HBO’s Succession or Showtime’s own Billions for an answer. But Black Monday isn’t a brilliant dark tragi-comedy about family dysfunction. And it also isn’t a sharply written, pop culture-obsessed series about power and, well, yes, greed — at least not yet. But there’re signs the series can get there, so long as it doesn’t begin to drown in its tendency to depict the highs (drug-induced and otherwise) of overabundance present in its setting. This is, after all, a show that has Don Cheadle high-five a robot butler after doing a line of cocaine, and, just in case the show was entirely too subtle in its approach to the notion of excess, Black Monday features not one, but two roles for Ken Marino. 

Regina Hall in Black Monday Showtime

Efforts to mitigate those concerns fall largely on the capable shoulders of Regina Hall, who is coming off a string of strong performances in Girls Trip, Insecure, The Hate U Give, and the superb Support the Girls. Here, Hall plays the similarly alliterative Dawn Darcy, a tough, no nonsense trader who gives as good as she gets in a male-dominated workplace. It’s a role Hall is well suited for. Dawn is no shrinking violet when it comes to saying what’s on her mind or appearing to physically dominate the weaker men in the shop. Though she’s usually the only woman with a hint of power in whatever scene she’s in, Hall’s not alone in the cast, as Happy Endings alum Casey Wilson also takes a authoritative role as Blair’s demanding girlfriend, Tiff. While Wilson has the comedic chops to turn Tiff’s confrontation with her coke-dusted and jobless boyfriend into some solid slapstick, the character is, in the premiere anyway, revealed to be little more than a plot device, one central to Maurice’s long game that will, presumably bring about the titular October event. 

The series walks a fine line with regard to its depiction of the social norms in ‘80s, especially as they pertain to traders on Wall Street, and what audiences of 2018 and 2019 may be looking for in their escapism. That also pertains to the show’s love of putting bad, and since it’s still 2018, “toxic” behavior on screen. Black Monday attempts to make up for such potential shortcomings by introducing a surprisingly straightforward plot that paints Maurice as some sort of three-dimensional chess genius, planning out his moves well ahead of his opponents. That lends the series a caper-like quality, one that leavens things considerably, and, when coupled with a frenetic performance by Cheadle and Hall’s dynamism, makes for a series with some potential to be more than just a coke-fueled ride through the "Greed is good" era.

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The Black Monday series premiere is currently available on sho.com, the Showtime app, YouTube and Facebook. The series will officially premiere on Sunday, January 20, 2019 on Showtime.

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