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Don Cheadle Keeps Showtime’s ‘Black Monday’ Rolling

Don Cheadle in Showtime's Black Monday
Don Cheadle revisits Wall Street’s go-go 1980s as Mo Monroe in Black Monday. (Image credit: Nicole Wilder/Showtime)

Season three of comedy Black Monday, with Don Cheadle playing Wall Street hotshot Mo Monroe, begins May 23 on Showtime. About a motley bunch that causes a colossal stock market crash, Black Monday also has Andrew Rannells and Regina Hall in the cast. 

Cheadle, an executive producer, spoke about his various TV and film projects, including a redo of The Wonder Years on ABC. An edited transcript follows. 

B+C: For those who don’t watch Black Monday, why should they start watching?

Don Cheadle: I think it’s a very funny show. It’s a sitcom on cable, which is a rarity. It’s an excellent cast and a hilarious time to unplug your brain and just plug into some funny. And it’s good escapism. 

B+C: What drew you to the show in the first place?

DC: As always, it’s the material first. I read the script and it made me laugh. The characters were very surprising and different. It was subject matter that we’ve seen in films and always dealt with in a more serious way. To do it under the auspices of Seth and Evan [executive producers Rogen and Goldberg] and their insanity was a cool spin on material we’ve seen before.

B+C: The show is set in 1987. What makes it timely in 2021?

DC: The substantive similarities of what we are dealing with and what Wall Street deals with — guys with a robber baron mentality, win at all costs and fuck over whoever you have to, to get what you want — we can see in a lot of demonstrable ways how some of that hasn’t changed very much. It allows us to get a perspective on, and to play with, under the auspices of comedy, things like race, politics, power dynamics and gender dynamics. This has been going on since time immemorial and now we’re just starting to say, ‘Hey, maybe it’s not OK to embarrass me in front of the whole office and throw a book at my head.’ 

B+C: What will we see in the new season?

DC: The characters are all on their own trajectories and we’re gonna find our way back to one another. Dawn is in prison. Mo is trying to start this new company and Paul Scheer’s character, Keith, is ensconced with the Lehman brothers. We find Blair pursuing his political ambitions and being a complete sellout. 

We’re dipping into all it right off the bat and figuring out how these guys come together. That is very artfully done in a really interesting, plot-twist way. 

B+C: How much was COVID-19 an issue in production?

DC: Very much so, like it is everywhere. We’re getting tested every other day; everyone’s in masks and shields. As soon as you say ‘cut,’ everyone puts their masks on and shields up. It’s the third production I’ve done under these conditions and it’s just very bizarre. And very necessary. If we’re going to do it, this is the only way to do it. 

B+C: How many seasons do you see Black Monday going?

DC: Who knows? If there’s more to do and people are having fun, there’s always gonna be a place to go. There’s no dearth of problems with the financial sector to deal with. There’s a lot of room to play with, with these characters. 

B+C: What drew you to ABC’s The Wonder Years?

DC: Again, the script. The people behind it. And the opportunity to take this iconic story and these iconic characters and this part of quote-unquote Americana and look at another part of Americana that’s often not looked at and what it means for the wonder years of young Black kids and their friends in Alabama during this period. I think it’s just an interesting spin on that material. 

B+C: With all the characters you’ve played in TV and film, is there one that you find yourself coming back to more than the rest?

DC: I can’t pick one. I’m very fortunate in that I’ve been able to be in a lot of quality movies and TV shows, and theater as well. I’ve been very lucky to play a lot of interesting and rewarding characters, from Mouse [in Devil in a Blue Dress] — that’s one where you’re like, wow, that was cool to be able to do that with Denzel. Talk to Me, playing Petey Green. Paul Rusesabagina in Hotel Rwanda. Even Basher in the Ocean’s trilogy. 

I could go down the line. It’s hard to pick one. All of them, for different reasons, bring a smile to my face because of the experience, the people I got to work with, the project overall. 

We create these little nuclear families and then go off to the corners of the Earth. It’s cool to have had the ability to do that with so many talented people over the years. Thirty-plus years I’ve been doing it — I’m very blessed.