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‘Black Monday’ Review: Energetic Wall Street Dramedy Doesn’t Pay Dividends

The comedic half of this new series about the stock market crash of 1987 is a rollicking good time, but its dramatic side takes a nosedive

Don Cheadle, Andrew Rannells and Regina Hall in 'Black Monday.'

Don Cheadle, Andrew Rannells and Regina Hall in 'Black Monday.'

Miller Mobley/Showtime

In the second episode of Showtime’s new Eighties Wall Street dramedy Black Monday, the main characters are shadowed by a screenwriter who’s working on what will become Oliver Stone’s Wall Street. At one point, Regina Hall’s Dawn is in the midst of lecturing a colleague when she’s startled to notice the writer lurking nearby. “Greed is… good Lord!” she exclaims. “Are you trying to hide behind a lamp?!?!”

There are two basic ways to approach a period piece. One is to adopt the psychologies of the characters and their era. They can speculate on what the world may become, but to them, they’re in the present, and everything about it is real and serious and normal. The other way is to constantly wink at the audience about how ridiculously people used to dress or talk or act, to have the characters say things that only the viewers will laugh at — for instance, a certain Wall Street catchphrase that would win Michael Douglas an Oscar — because we’re enjoying it all from an ironic distance.

Black Monday, as you might gather, takes the latter approach. Created by David Caspe (Happy Endings) and Jordan Cahan, the series (it premieres Sunday; I’ve seen three episodes) generates some laughs at its own self-awareness, as well as the sheer energy of stars Don Cheadle, Hall and Andrew Rannells. But those jokes ultimately undercut any attempt to take the characters and their story seriously, which the show very much wants you to do.

Thus, a fictionalized version of the events leading up to the very real, very catastrophic Wall Street crash of 1987 plays like a mixtape of Showtime’s Greatest Hits: The finance-bro cockiness of Billions meets a jheri-curled Cheadle dialing up his House of Lies persona while hoovering drugs like he’s Nurse Jackie. Playing an out-of-control, bullying trader named Mo with more swagger than sense (he rides in a Lamborghini limo, even though, as Rannells’ panicked rookie trader Blair points out, it offers “none of the speed of a Lamborghini and none of the comfort of a limousine”) is a terrific showcase for Cheadle’s verbal dexterity. The straightforward comedy take on this material would be a fine fit for him, for Rannells and for most of the show’s cast, which also includes Paul Scheer as Mo’s sneering lackey Keith, Casey Wilson as Blair’s fiancée Tiff and, playing the twin Lehman brothers, Ken Marino. As Dawn, the one woman at their renegade firm, Hall is used mostly as a disapproving foil for Mo and the guys, but she spars well with Cheadle when allowed to. Billions is more entertaining with its own “boys will be boys” gamesmanship, but Cheadle alone would be worth the price of admission to its Reagan-era equivalent.

When things turn more sober, however, the raised-eyebrows vibe really causes problems. Cheadle and Hall can deftly toggle between the show’s funny and dramatic sides and make them feel like parts of a whole. But other areas of the series — particularly anything having to do with Blair, both at the office and at home with Tiff — are pitched so broadly as to make the stabs at profundity elsewhere feel like a put-on. The best blend of the two comes in the third episode, via a subplot about Keith trying to juggle multiple professional and personal responsibilities on the day of his son’s bar mitzvah; for a few moments, it feels like Black Monday has figured out how to be comic and tragic at the same time. That the show improves a bit as it goes along is a promising sign, but too much of it still seems to be written in air quotes. And the actual mystery of how these marginalized knuckleheads are allegedly responsible for the eponymous crash doesn’t feel real or compelling enough a hook to pull the shorter-term stories along.

There’s good raw material here. Just don’t buy until we see if the creative team can land on a consistent and satisfying tone.

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