If all you saw were the posters when it first premiered last year, you really couldn't be blamed for not seeing Showtime's Black Monday as a den of comedic delights. On the surface, it had all the signs of yet another show about financial titans behaving badly and engaging in the kind of morality-free, high-decadence lifestyle that has repeatedly led America to ruin. What was there to separate this show from Showtime's own Billions or even HBO's (altogether excellent) Succession? Even star Don Cheadle's presence brought to mind his previous Showtime series House of Lies, which was technically a comedy, but in that very Showtime mold where it was a mix of dark comedy and edgy melodrama that often tips towards the latter.
As those who've seen it can attest, however, Black Monday is not only a legitimate comedy, but also one of the funniest ones on TV right now. And the key to that most welcome surprise is a comedic sensibility borne of a dearly departed 2010s series: ABC's Happy Endings. That series was created by David Caspe, who co-created Black Monday, and whose fingerprints are all over it once you look beneath the surface.
The surface, of course, is where the premise of Black Monday lies: Season 1 begins one year before the 1987 stock market crash known as "Black Monday." We're following the story of the Jammer Group, a lower-level investment firm headed by Cheadle's Mo Monroe. Perhaps the least comedic character on the series, Cheadle drives the show's storyline, which includes a rocky relationship with his business partner Dawn (Regina Hall). In the pilot, Mo recruits hotshot newbie stockbroker Blair Pfaff (Andrew Rannells) as a play to get his finger in the pot of the insanely wealthy Georgina family, as Blair is about to get engaged to Tiff Georgina (Casey Wilson).
If Casey Wilson's presence on a show co-created by David Caspe pinged your radar, it should, as Wilson is not only married to Caspe, she was also part of Happy Endings' A+ ensemble. If you watch enough Black Monday, that connection really emerges, as Tiff lets loose with more and more line deliveries that feel like they'd be equally at home coming from the mouth of Penny Hartz.
This is a phenomenal scene from season 1 of BLACK MONDAY, with Casey Wilson in full Penny Hartz mode. pic.twitter.com/xjs0lTkU99— Joe Reid (@joereid) March 12, 2020
Casey Wilson is just the tip of the iceberg when it comes to the deep bench of comedic talent at work here, with so much of it playing like a quasi-Six Degrees of Separation game. We've got Paul Scheer — who is married to June Diane Raphael, Wilson's longtime comedy partner — playing a closeted Jammer trader named Keith; Ken Marino, who starred opposite Wilson in the short-lived NBC sitcom Marry Me, plays a pair of twins who are Mo's bitter rivals; Horatio Sanz, who preceded Wilson on Saturday Night Live, is also on team Jammer; and Wilson's current podcasting co-host on "Bitch Sesh," Danielle Schneider, plays an SEC investigator.
Then there's the tremendously funny work being done by the leads. Regina Hall, who has long been an underrated comedic performer, gets to shine in a role that allows her to show off her pitch-perfect comedic delivery, while also grounding the show with its most sympathetic character. And anyone who's seen Girls (or The Book of Mormon on Broadway) knows that Andrew Rannells is fantastically funny; he's perfect in the role of a novice who's just entered the belly of the beast.
So if you were thinking that Black Monday is just a cheap gloss on The Wolf of Wall Street, there's no need. While the bad-boy antics of other shows and movies about Wall Street are present, the sharply written, perfectly delivered comedy more than makes up for it. And in 30-minute, highly bingeable episodes, you can catch up awfully quick.
Black Monday kicks off its second season on with two back-to-back episodes Sunday March 15th, beginning at 10:00 PM ET on Showtime.
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Joe Reid is the Managing Editor at Primetimer and co-host of the This Had Oscar Buzz podcast. His work has appeared in Decider, NPR, HuffPost, The Atlantic, Slate, Polygon, Vanity Fair, The Herald Sun, Vulture, The A.V. Club and more.