Showtime Remembers 'Black Monday' on Anniversary of Stock-Market Crash 10.19.2018 On the 31st anniversary of the 1987 global stock-market crash known as 'Black Monday,' Showtime released the first official trailer for its upcoming 10-episode series of the same name. Starring Don Cheadle, Andrew Rannells and Regina Hill, the series tells the fictional story of a group of outsiders who take on Wall Street's elite, and the result is global financial meltdown. Besides Cheadle, Rannells and Hill, the series also stars Paul Scheer (The League). The list of guest stars is long and legion, including Yassir Lester (Making History), Horatio Sanz (Glow) and Michael James Scott (Aladdin on Broadway), with recurring guest stars Casey Wilson (Happy Endings), Ken Marino (Wet Hot American Summer), and Kurt Braunohler (Bunk). Bruce Dern (Big Love), Melissa Rauch (The Big Bang Theory), Julie Hagerty (Airplane), Kadeem Hardison (A Different World), Eugene Cordero (Kong: Skull Island), Vanessa Bell Calloway (Shameless), Tim Russ (iCarly) and Jason Michael Snow (The Book of Mormon) also have signed on as guest stars. The series, which is a co-production between Showtime and Sony Pictures Television, comes from Seth Rogen and Evan Goldberg (Preacher, Future Man) who executive produce and directed the pilot. David Caspe (Happy Endings) and Jordan Cahan (My Best Friend's Girl) serve as executive producers and showrunners. Black Monday premieres Sunday, Jan. 20, 2019, on Showtime..