Why David Caspe is the Master of Cult Television

Prestige television has become a crowded space, but Black Monday, a Don Cheadle-fronted comedy about the 1987 stock market crash, ranks among the funniest, even as it confronts issues of race, gender, class and sexuality. Creator David Caspe has been making interesting television for a decade, winning over critics and fans with his absurdist — but heartfelt — comedy. With Black Monday, the Chicago-born writer proves he’s the master of cult TV comedy.

Where did the idea for Black Monday come from?
The line we always say is like, “Look how far we haven’t come.” That’s sort of the writers’ room ethos of the show. I created the show with my close friend Jordan Cahan – we grew up together – and we had always wanted to try to do a comedy that had the plot twists and the plotting of a binge-able cable drama [that was] funny enough but still has the crazy stakes that you could actually buy some of the twists without it flying off the handles.

My dad was a soybean trader back in Chicago, which is different than Wall Street but not too dissimilar, and he would always tell me stories as a kid of just the craziest shit that would happen down there. Like, he would walk into the bathroom and guys were just doing coke everywhere. It has since been pointed out to me in the writers’ room by a lot of people like, “Don’t you find it strange that your dad has all these stories?” Like, [he was always saying] “as I was going home” or “when I walked by” but, you know, he never was part of it? You likely don’t have that many details unless you were in it.

Black Monday

I think those crazy stories were both hilarious but also really just heartbreaking because the stakes are so high in that world. There’s not really a lot of jobs where you can lose money when you go to work; very rarely do they take all the money you made the last four years and just take it back. I think I would also need a drink or a line or something at the end of the day if I spent all day almost losing everything, and my house and my kids’ future. We always say if, in the movie Wall Street, which was an Oscar-nominated drama, Gordon Gekko had a robot butler, then we don’t have to stray from reality that much to get jokes.

We did an episode in the first season called the LaGuardia Spread, where Horatio [Sanz’s] character made a big bet on beef or cattle, then went to the airport with the plan of either finding out it worked and going back to his house, or finding out it didn’t work and disappearing forever. That was something my dad told me called the “O’Hare Play”, which is obviously the Chicago O’Hare Airport. When guys were down to their last nickel and had no choice, they would borrow a bunch of other people’s money and make an enormous trade, and then they would go to O’Hare and call the [trading] floor. If it worked, they’d come home a hero. If it didn’t, they would just hop on an airplane and disappear truly forever. My dad knows multiple people who just left their wife and kids and never came back. We wanted to try to mimic that tone of ‘80s movies, of yo-yoing between super dramatic and then super slapstick comedy in a way that movies just don’t do anymore.

Well, Don Cheadle, former Sharp cover star, was nominated for his second Emmy for the show, so you’re doing something right.
Don Cheadle is a genius and when he came on to the show, the three of us [Caspe, Cahan and Cheadle] really honed in on his character with him. He was instrumental in forming the character in the show, as are all the actors, like Andrew Rannells, Regina Hall, Paul Scheer, Casey [Wilson] and Ken Marino, Yassir [Lester] and Horatio [Sanz] – everybody really. We run a very collaborative ship.

Don Cheadle

Collaboration seems evident in everything you’ve done, from Happy Endings to Champagne ILL. The “group hang energy” has translated to an ardent fanbase for your work. What’s the secret sauce to creating cult TV?
Gosh, I don’t know. You may be one of 10 people that saw Champagne ILL. But that’s so nice to hear, I’m so proud of that one. I also created that with my friend Jordan Cahan and the Libman brothers, who we also grew up with. So, I don’t know what the secret is to making shows that no one watches. I gotta be honest: I thought that one came out really funny. It was such a collaborative effort with so many great writers, and Adam [Pally] and Sam Richardson are once-in-a-generation geniuses. It’s just making what me and my friends think is funny, and the people that it does appeal to seem to really like it, and I would take that over anything else.

And what’s it like working with your wife [actress and writer Casey Wilson], one of the funniest people in the world?
I trust her opinion the most as far as comedically, writing-wise or anything. It’s truly a blessing. She’s also willing to do whatever is best for the show or movie or joke; she takes all vanity out of it. On Black Monday, I’m just like, it’d be so great if in the opening scene of episode two, we find Casey’s in bed with someone, and when she kicks this guy out, he’ll be completely naked. In the ‘80s, there was so much gratuitous female nudity, but never any no one’s really ever done just gratuitous male nudity. So, we made a decision early on: no female nudity in the show ever, only male nudity. And I was like, just so excited by that concept. Just artistically it felt like an interesting, bizarro ‘80s entertainment.

The Happy Endings cast just reunited for a Zoom episode. Where would the gang be today?
Alex, Elisha Cuthbert’s character, would obviously be an anti-masker COVID denier. And we always want to see Penny get broken up with in a horrible way. Brad is always taking staycations. Dave, of course, would be at that Jared Leto retreat and not realize there’s a pandemic. No one is more type A than Jane or would take the take more seriously. And Adam Pally’s just a fuckin’ crazy person. He would have eaten all his food day one and eat nothing but weed edibles. I think that’s about where they would be – nowhere, basically.

This interview has been condensed and edited for clarity.