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‘Black Monday’ Trailer: Don Cheadle Takes Over in Showtime Comedy About Historic Wall Street Crash

Andrew Rannells and Regina Hall co-star in The Program Formerly Known as "Ball Street," the network's first big programming swing of 2019.

Black Monday Don Cheadle Trailer

Showtime

Hollywood’s been no stranger to Wall Street, but with the help of Don Cheadle and Andrew Rannells, one new Showtime series is looking to dig deep into one of the financial sector’s darkest hours. (With laughs, of course.)

Black Monday” is one of Showtime’s biggest 2019 bets, a comedy about the lead-up to and aftermath of October 19, 1987 (yes 31 years ago, today), a day of a global money meltdown that saw nearly a quarter of the Dow Jones average disappear almost overnight.

Giving that day the “Big Short” treatment, this ten-episode series will chart the exploits of high-stakes Wall Street player Rod “The Jammer” Jaminski (Cheadle), who entices pure-intentioned Blair Shmerman (Rannells) to join his team. Fresh off a summer of “Support the Girls,” Regina Hall plays Jaminski’s second-in-command.

The trailer below definitely has some “Wolf of Wall Street” vibes too, featuring some trading room antics and some slow-motion realization that money situations are about to get very bad very soon. There’s also a quick glimpse of generic, off-brand version of Mr. Met, which, given that the Mets were still technically world champions on that day despite missing the playoffs fits in pretty well, thematically.

Executive producers Seth Rogen and Evan Goldberg directed the pilot of the series created by David Caspe and Jordan Cahan. Caspe is the erstwhile boss of “Happy Endings,” and it seems as though he’s brought some alums from that project here too. Ken Marino (as twins, apparently?!) and Casey Wilson headline an impressive supporting cast that also includes Paul Scheer, Kurt Braunohler, Bruce Dern, Melissa Rauch, Julie Hagerty, and Eugene Cordero.

Watch the full trailer (including the original Showtime intro from three decades ago) below:

“Black Monday” premieres January 20, 2019 on Showtime.

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