‘Black Monday’ Season 2: How Things Get Crazier For Don Cheadle, Regina Hall, Andrew Rannells and Paul Scheer After the Crash

Season 1 of Black Monday offered an alternative history theory to what caused the 1987 stock market crash. It turned out, The Jammer Group’s in-fighting and scheming crashed the whole market. Now Don Cheadle, Regina Hall, Andrew Rannells and Paul Scheer are back for another season.

Season 2 picks up with Mo (Cheadle) on the run for the crimes of Season 1. Dawn (Hall) is running her own brokerage firm. Blair (Rannells) is now married to Tiff (Casey Wilson) and Keith (Scheer) has come out. The cast and creators David Caspe and Jordan Cahan were on a Television Critics Association panel for Black Monday on Jan 13 discussing the new season. Season 2 premieres Sunday, March 15 at 10 p.m. on Showtime.

‘Black Monday’ Season 1 has a lot to answer for 

Cahan and Caspe had their work cut out for them explaining the Black Monday crash with their fictional characters. Now they had to figure out what comes next.

“I think Season 2 is kind of like who is going down for the crime?” Cahan said. “So we saw the how, and then I think the mystery really continues. Our show does have consequences and stakes, and it’s who’s going to pay for that? So that guided the writing and the writers’ room.”

Don Cheadle and Regina Hall have a tricky relationship

Mo and Dawn were constantly one upping each other throughout Season 1. In Season 2, Black Monday flashes back to their relationship prior to The Jammer Group. It was just as frought then, and it doesn’t get easier when Mo returns. 

“I think that they are constantly trying to figure out the same question,” Cheadle said. “Like, where is this headed? What are we going to do? What part of us is the business part of us, and what part of us is the personal part of us that we’re trying to service at the same time? And can they coexist? I think that question is this season is rife with that question for these two characters.”

It’s even muddier for Dawn before and after Black Monday.

“Can you trust someone in love who you don’t trust in business?” Hall asked.

Andrew Rannells says Blair is going to go dark after Black Monday

Blair married Tiff for a stake in her family’s company. When Tiff found out about it, she agreed to the sham wedding as long as she was a partner. Now they’re married and the Black Monday crash occurred, and Rannells says things get even darker for Blair. 

“We sort of left Blair at the end of Season 1 on the precipice of making a lot of personal decisions,” Rannells said. “Then this season we really got to launch into them, and he gets dark real fast. Sometimes after these table reads, Jordan and David would be, ‘This is still a comedy, right? We are still doing a comedy, right?’”

Paul Scheer on the new Keith

In Season 1, Keith hid his sexuality from his coworkers and tried to join in their aggressive heterosexuality, unsuccessfully. Now that he’s openly gay, it’s a relief, but only a temporary one, Scheer said.

“He’s out, and he’s proud. He’s living in a world that he can shed everything that he’s had to hold inside for all that first season, but at what cost? What consequences come with that? I think everyone’s kind of dealing with that in the show, like, ‘Oh, I finally got what I wanted, but now where does that kind of pay off?’ And not quickly, but these characters do kind of come back towards each other, and old patterns have to come back into play. So he’s happy and then he starts to be very unhappy again, based on situations that start to pile up.”

‘Black Monday’ could continue to the ‘90s

Season 2 picks up after the Black Monday crash of 1987, but it shouldn’t take long for the show to catch up to the ‘90s. Caspe would love to go even further than that.

“I would love to do the ’90s and the 2000s,” Caspe said. “As long as they’ll let us continue to make shows, I think we’ll continue to make them. We don’t have a lot of creative integrity up here.”

There was another stock market crash in 2008, and Caspe expects there to be infinite material for Black Monday.

“There’s going to be another crash,” Caspe said. “The question now is will the stock market crash before the world explodes?”

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