Black Monday (Seasons 1–3)

Black Monday (2019) is a Showtime crime comedy you can watch online on iFILM, starring Don Cheadle, Regina Hall, and Andrew Rannells.

The show positions itself as the untold origin story of October 19, 1987 — Black Monday, the worst single-day drop in Wall Street history. Mo Monroe (Cheadle) runs a scrappy brokerage full of outsiders. He and two Yale graduates stumble into a plan to take on the establishment, and somehow pull off one of the biggest financial disasters in American history in the process.

Executive-produced and partly directed by Seth Rogen and Evan Goldberg, the series runs on absurdist momentum — big hair, bigger personalities, and a premise that escalates with every season. Three seasons in total. Don Cheadle doing comedy this committed is not something to skip. Stream Black Monday (2019) online on iFILM.