Oct. 19, 1987, was a dark economic date. It was when the worst stock market crash in Wall Street history took place. Three-plus decades later, this financial tragedy is serving as satirical fodder for Black Monday, a new Showtime series that shares the same nickname as that ill-fated day.
Created by David Caspe and Jordan Cahan, it stars fellow executive producer Don Cheadle, who plays Maurice “Mo” Monroe, the head of the Jammer Group. This renegade Wall Street investment firm is rounded out by a misfit crew driven by Dawn Darcy (Regina Hall) and Keith Shankar (Paul Scheer) who cross paths with Blair Pfaff (Andrew Rannells), a wide-eyed trader ripe for manipulation. With the comedic team of Seth Rogen and Evan Goldberg serving as executive producers and writers, it’s the kind of comedic project Scheer was eager to jump onto after being an integral part of the FX series The League for seven seasons.
“I’m friends with David and Jordan, who created Black Monday. Years ago, they said they had this idea about Wall Street and they had this part they thought I’d be really good for. I said I’d love to do it, but I couldn’t do anything because of The League and David was doing Happy Endings at the time, so it just faded away,” Scheer said. “About last year this time, I got a call from them again and asked if I remember that show they initially proposed. I said yes and they said they wanted me to meet Don [Cheadle] for the part. It was originally written for a guy in his late ’60s and they wanted to see my take on it. So I came in and read with Don and that’s how the part came together.”
With the show being set in the mid to late 1980s, there are plenty of cultural references thrown in, whether it’s the video game Duck Hunt, the then-recent World Series champion New York Mets or nods to workplace films Wall Street and Working Girl. And while Scheer was only 11 when everything hit the financial fan on that long-ago date and was more caught up with begging his parents to let him stay up late watching television and taking him to see Planes, Trains & Automobiles, he dove into his Wall Street research with great relish.
“I was finding a lot of great BBC documentaries about people that trade on the floor and the culture there,” he said. “There’s something interesting about traders. These people are essentially living the life of a rock star, without any of the fame or success. It’s just the wealth part. So they are acting insane during their days and making all these cutthroat decisions and a lot of them have to come home to a family. Part of the fun of these documentaries was that you’d see these people on the floor who were just these animals and then go home and play with their kids. But you’re basically putting more stress on your throat and heart from eight until noon and you have the rest of the day off.”
With Cheadle setting the tone for the series, the narrative takes twists and turns that perfectly capture that era’s financial excesses, be it the main character’s use of a stretch Lamborghini, high-stakes wagering on mundanities and the rampant use of cocaine, all fueled by alpha male-driven braggadocio. And while it’s framed with humor, there are a surprising amount of dark and dramatic turns that pop up, particularly when it comes to Scheer’s character.
“When I first heard about the show, it was about seeing a character that was much more complex than what I had seen in a comedy, and that was exciting. I love what these guys have been really able to do. While this is a hard comedy, they are adding some of these beats that I love from dramatic shows like Better Call Saul that has a serialization to it,” Scheer explained. “I think a lot of the times when you hear the word dramedy, it’s a lot more drama and a lot less comedy. And I think what they’re trying to do here is balance it.
My character is clearly putting on this very aggressive persona to mask what he’s dealing with in his personal life that, at the time, was not accepted. We are a firm of underdogs, but it’s a little bit deeper than just being The Bad News Bears and I really like that. It’s one of those shows that, as we shot it, I had an idea of what was going to be happening over the course of the season. But when we shot our last day, I literally had no idea where this goes in season two, because everything matters.”
With a number of projects in the docket—a couple of podcasts, writing a comic book series, and myriad television guest appearances, the veteran sketch comedian’s television face time is even more ubiquitous. But given the level of talent his three main castmates bring to the set on a day-in and day-out basis and the quality of writing he’s working with on Black Monday, Scheer realizes the unique opportunity he’s been given to be a part of this.
“All three of [my costars] are incredibly playful, fun and ridiculously talented. They want to make the best thing and there are no egos there,” he said. “It’s all a team sport, given that we’re the four regulars on the show. Coming into that world, I felt incredibly well received, although daunted.”
Black Monday is currently airing on Showtime on Sunday nights.