Don Cheadle lives the wild life in 'Black Monday'

The 10-time Emmy nominee Don Cheadle photographed in Los Angeles, July 2020.

Aug. 19, 2020 7:30 AM PT

The exploits of “Black Monday’s” coked-out, amoral Wall Street pirates and ’80s fashion victims might elicit some sort of crazy cautionary tale, but any lessons therein don’t ever seem to be learned in the real world. You can almost hear some viewers cheering them on: “Greed is good, greed works.”

“And we look at those people and go, ‘Holy s—, no! No!’” says series star, producer and current Emmy nominee Don Cheadle, laughing. “One of the books I studied — I’m forgetting the title — in the foreword, the author says, even though we’ve advanced, you talk about how we’ve attempted to police these things; the one thing that never gets taken out of the equation is people. And one thing people have is greed. If certain people have the opportunity to take advantage, they’re going to do it until they get stopped.

“So yeah, for some it’s not a cautionary tale, for some it’s terrifyingly like a prescription,” he says with an even bigger laugh. “But hopefully, for those of us who see what actually happens to the human beings afterward, ‘Win at any cost’ is not a motto to live by.”

Showtime's "Black Monday" is set in the craziness of '80s Wall Street. Pictured: Andrew Rannells, Don Cheadle, Regina Hall.

Among the gonzo comedy’s secret weapons (apart from Cheadle’s array of hairpieces) have been two traders from the time: one of Cheadle’s good friends and the father of series cocreator David Caspe. Both have provided eyewitness accounts of everyday madness.

“How drug-fueled it was. How completely outrageous it was. How people were really allowed to be driven by their id, and destruction was just a part of the game,” Cheadle says of what he learned from his research. “It wasn’t enough to win; someone had to be dead on the other side of the field.”

In its first season, the dark comedy established that it was not afraid to go there, into the unrestrained chaos of ’80s Wall Street with a twisty mystery-heist vibe. Cheadle’s Mo Monroe has a checkered past and more secrets than you’d expect a guy who’s about 95% id would be able to keep. He’s an ultra-rarity for the time: Not just a Black stockbroker but one who also runs his own shop, the Jammer Group. He’s a snorting, scheming libertine who somehow seems to get away with everything, even as his arguably smarter lieutenant and ex, Dawn (Regina Hall), battles through ingrained sexism to make her mark, and a closeted new guy, Blair (Andrew Rannells), wrestles with his own demons to become a power player.

This year’s Emmy nomination is Cheadle’s 10th overall, and his second in as many seasons playing Mo. In Season 2, he says, “I think we take on more issues. We always wanted to be topical and look at what’s happening in the world and view it through this ’80s lens and see how we can apply what we know now to what we knew then and vice versa. How does each timeline comment on the other timeline?”

Trailer for Season 2 of “Black Monday” on Showtime.

Season 2 includes pointed references to recent events and political figures. One of the subplots finds Blair leveraging his newly confident sexuality to push for deregulation that would eventually become linked to the real-world 2007-2008 financial collapse. There are crooked evangelists and merciless FBI agents. Dawn gambles recklessly with the equivalent of the United Negro College Fund. There’s a bank shootout that Cheadle gleefully describes as “‘Wall Street’ meets something by Sam Peckinpah.” There’s even a horror-tinged revenge subplot.

“We thought, ‘How can we weave all these things together and still be under the umbrella of the stock market and being a trading company?’ By the end of the season, we’re sitting in the detritus of what those big deals and this investigation has done to us.”

When it comes to Mo’s arc, it may be long, but whether it’s bending toward justice is an open question. After multiple betrayals at the end of Season 1, he’s not seeking revenge at the start of Season 2; he’s searching for “Kokomo.” He’s living a peaceful, drug-free, pseudo-tropical existence. Then his frenemies find him and make the mistake of trying to officially end his Wall Street career.

“He has that dream of being a guy who tours around between hotel bands and maybe just walks the Earth like Kwai Chang Caine. But as soon as they try to push him out, as soon as they try to ‘win’ against him, Old Mo comes back and he has to win,” Cheadle says of the awakened beast. But, he adds, what keeps them all from flying out forever into the feral stratosphere of drug- and winning-fueled insanity is the tether of real feelings some have for each other.

There is no defense: Don Cheadle, staying safe during the pandemic, chatted with The Los Angeles Times about "Black Monday."

He recalls a scene between Mo and Keith (Paul Scheer), one of the friends who betrayed him. They reminisce about the good times they had on the run when it was just them and a Nintendo machine. Then Mo says, “ ‘Yeah, I am nostalgic for that. But now I’m gonna f— you and I’m gonna go get these guys too.’

“That thing is there, under them, always aching to come out, to just be a [regular] person. But they’re on a path they’ve chosen — and if they ever did [reform], the show would be over. So they’ll stay these people for a little while.”

Greed is good — for laughs with Don Cheadle and ‘Black Monday’

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