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‘Black Monday’ Review: Regina Hall Makes Showtime’s ‘Wolf of Wall Street’ Wannabe Worth the Risk

Don Cheadle and Andrew Rannels' new comedy has the red flags of an inflated stock, but it's hard not to invest in this leading lady.

Black Monday Showtime Don Cheadle Regina Hall Paul Scheer

“Black Monday”

Erin Simkin / Showtime

Outdated and overextended aren’t desirable qualities for stocks or TV shows, but “Black Monday” makes them work to its advantage — for now. Showtime’s new comedy follows a greedy, drug-addicted, morally bankrupt but monetarily flush stock trader whose dangerous play for one company may have caused the worst stock market crash in the history of Wall Street. Despite saying as much right off the bat, David Caspe and Jordan Cahan ask you to root for Don Cheadle’s Maurice “Mo” Monroe anyway, marking yet another TV series mistakenly built on an antihero story (so very out of fashion in 2019) and told at such a rapid rate one wonders how “Black Monday” will sustain interest beyond its first episodes.

But oh what fun lies within these initial 90 minutes. There’s Don Cheadle’s coked-up charm and a robot butler named Kyle; there’s a “Marry Me” reunion with Ken Marino playing identical twin Lehman brothers and Casey Wilson as a spoiled rich kid who’s as quick to slap her would-be hubby as she is to crush his reproductive parts; there’s ’80s jumpsuits, baggy suits, white suits, and track suits; there’s a bright red Lamborghini limousine — a lambo limo, a limbo —  with a recurring role; there’s a murder-mystery to unravel, and an acknowledgement of “Top Gun’s” homoerotic overtones by people who just saw “Top Gun” in theaters. And towering above it all is Regina Hall, ready and waiting for the solo spotlight she deserves, but making the most of one more supporting gig.

The “everything and the kitchen sink” approach taken by Caspe and Cahan pays dividends up front: Their episodes race by with loads of joyful enthusiasm, even as they’re laced with doomed morose. “Black Monday” is named after and framed around the historic day of trading that sent stock brokers throwing themselves off buildings, and one such suicide is shown in the first scene when someone wearing a familiar gold watch and green tie pin crash lands on the beloved red limbo. Who is it? Is it Moe? Is it his wunderkind protege, Blair Pfaff (Andrew Rannels)? Is it Moe’s top trader and ex-girlfriend Dawn (Regina Hall)? Is it one of his lackeys, enemies, or a yet-to-be-made connection?

Black Monday Don Cheadle Showtime Episode 1

Don Cheadle in “Black Monday”

Erin Simkin / Showtime

From there, the story backtracks one year, recounting the events leading up to that fateful day and titling the episodes after how many days are left. (Episode 1 is “365,” Episode 2 is “364,” and Episode 3, lest you worry it’ll take 36 seasons to get to Black Monday, jumps ahead to “339.”) Each entry tracks the day-to-day activities of The Jammer Group, a bunch of party-loving traders led by Monroe who are trying to make a name for themselves on Wall Street. While their “Wolf of Wall Street” antics are entertaining and captured with an aptly furious influx, the flaw lies in their leader. Moe defines himself by two things: money and cocaine. Even though he asks for pity through his ailing love life, all signs point to his loneliness being self-inflicted, and the rest of his cruel, careless ‘nannigans will likely soon prove meaner than they are funny.

Still, he’s balanced out by a naively good-hearted new kid (Rannels), who’s sharp in his comic timing but a little familiar as a character, and even more so by Dawn, whose only flaw is an inexplicable attachment to Moe. She’s the best trader on the block; her hair is so high and bouncy she could lease it as a bouncy house for kids’ parties on the weekend; her fashion is as on point as one could hope for during the ostentatious ’80s, and she’s as quick with an insult as she is supportive of hearing a great one. In short, she’s got a clear goal — conquer the men’s world of Wall Street — and a whole lot of character. Why isn’t she leading the series?

There’s no good answer for that, but things could easily shift in her direction if Moe is the one who jumps off the building. “Black Monday” is overflowing with big, bold choices, daring you to be bored and winning that bet 90 percent of the time. (The pilot is even directed by Seth Rogen and Evan Goldberg, adding behind-the-scenes opulence to the onscreen banquet of excess.) But it’s also awash in red flags for a burgeoning series, as the lead character is a questionable, outdated pick and the premise begs for a quick resolution to the mystery being teased. But viewers could do a lot worse than invest in this likely crash — plus, Caspe already has one iconic, shoulda-been-a-bust series under his belt. Maybe he can add one more.

Grade: B-

“Black Monday” premieres Sunday, January 20 at 10 p.m. ET on Showtime.

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