Why Happy Endings' Creator Is Having So Much Fun Making Showtime's Black Monday

black monday showtime don cheadle regina hall andrew rannels

After creating broadcast network comedies like the beloved Happy Endings and the cancelled-way-too-soon Marry Me, creator David Caspe teamed up with writer Jordan Cahan to craft an entirely different kind of series, the financial crisis comedy Black Monday. With a star-studded cast fully binging and purging the outrageous excess of the mid-1980s, Black Monday is a cacophony of ideas, emotions, and humor. Speaking with Caspe and Cahan at TCA's winter press tour, I asked how fun it was to not by pigeonholed by seemingly any limitations. He said:

Yeah, it's super fun. I mean to get to kind of just do like, you know, [anything]. We tried to create what we thought was a different tone – I'm sure we're not the first ones there – but a tone that just combines all of our favorite things from all different types of TV shows and movies. And then also, at the same time, kind of parody the form of '80s tone and '80s TV shows and movies and stuff like that. And yeah, we felt like it's – it's cheesy to say – but kind of punk rock in that it's just loud and fast and everything and sloppy-on-purpose and just like kind of crazy. And I don't know, that just for whatever reason felt right, in the same way that world felt loud and crazy, and that decade in general.

At another point in the conversation, Jordan Cahan brings up a perfect example of everything David Caspe was talking about just above: Gordon Gekko's giant robot butler in 1987's Wall Street. The idea there is that, if a serious (for the time) Oliver Stone Hollywood drama was cool with including such an egregious example of misguided extravagance, then Black Monday could feasibly up the bizarreness ante with every episode. (Having Ken Marino play twins who may or may not be sexually involved definitely takes things up a notch.)

Black Monday is quite fun to watch, and looks like it was a blast to put together, since every scene is filled to the brim with kinetic energy, and each has the potential to either explode or implode, depending on how generous Don Cheadle's Maurice Monroe is feeling at that time. (Which generally comes back to how much cocaine is in his bloodstream.) That's the kind of show that Showtime was willing to make, which David Caspe can obviously appreciate.

But yeah, it's so fun to be on a network where we can actually like try all that shit and just like do something weird and different, and it's fun seeing people's responses. I think people either like fucking love it or hate it, which I think is a sign, at least, that it's different, I guess. Or that it's weird and hard to hard to understand and hard to put in a box. And, you know, I think it's kind of cool that people are having extreme reactions. [laughs]

Early reactions for Black Monday's pilot were indeed of the mixed variety, with most praising the comedy and the abundant vivacity, while expressing some confusion or worse about the story and the tonal balance. I can somewhat understand that, since Black Monday will hop, skip and jump from a sophomoric insult sesh to a multi-faceted monologue to a quiet moment of Regina Hall's brilliance, sometimes all within the same minute.

However, each episode continues to unlock more and more of Black Monday's twisting narrative , along with the secrets that these characters are hiding. Those over-arching elements were, for me, a lot more unexpected than seeing Paul Scheer's Keith become the butt of everyone's jokes due to his godawful hairpiece. Sorry, Paul and Keith, but it's the worst.

paul scheer's bad wig on showtime's black monday

For both David Caspe and Jordan Cahan, it probably would have been a far easier experience had they set Black Monday up as a more straightforward comedy show built on drug-fueled jokes with fast-paced deliveries. Here's Cahan talking about how hard it was, and rewardingly so, to take Black Monday above and beyond more limited genre labels.

At the same time, while I want to say it's incredibly fun to have the freedom, I think the difficulty of the show, what makes it so hard for us to write, is that we're trying to do hard jokes and hard comedy, but we're also trying to do tight plotting, and we're trying to give you cliffhangers and mysteries and twists you don't see coming, that you wouldn't see in a comedy. And then we're trying to do it all in a half hour or 28:20. So as far as the writing process goes, the trickiest part was like after you write the pilot, you're like, 'Whoa man, we did it! ' And then you go into Episode 2, and you're like, 'Fuck. How do I...how do we do...? What else are we hiding? We have to create secrets.'

Having only aired two episodes so far, Black Monday hasn't yet dropped any of the most eye-widening surprises scattered across this first season. Just don't be fooled into thinking such awe-inspiring shocks won't be coming around, or you might end up going off the deep end like so many did during the stock market crash of 1987.

Also complicating the storytelling process for the creators is the fact that Black Monday kicks off with a countdown set to close out on the infamous day of the title. David Caspe and Jordan Cahan confirm that Season 1 will definitely end on the crash in question, but there will most definitely be a lot of ups and downs before we get there.

Another thing fans can definitely expect is for Black Monday's central world and focus to start expanding as the season goes on. (And for Big Bang Theory's Melissa Rauch to rightfully keep giving Keith a hard time.)

Here, Cahan explains his fascination for that kind of plotting on television.

We're so influenced – at least I am, speaking for myself – by Mad Men, Breaking Bad...I mean truly, the Pantheon of amazing shit out there. And even some smaller stuff that I've had that I so admire and love, like Venture Bros., or like just the geeky stuff that I love that creates these worlds. The thing that I'm most impressed with is a world that can keep expanding.

Regardless of if you loved Black Monday or you hated it, it probably won't be the exact same show by the time its finale comes around and reveals who actually died. So you'd only be doing yourself a favor by tuning into Showtime on Sunday nights at 10:00 p.m. ET. Do take note, however, that there will not be a new episode on Super Bowl Sunday, and that Black Monday will return on February 10 at its normal time.

To catch up with all the other great shows hitting primetime as 2019 sets its feet, head to our midseason TV premiere schedule.

Nick Venable
Assistant Managing Editor

Nick is a Cajun Country native, and is often asked why he doesn't sound like that's the case. His love for his wife and daughters is almost equaled by his love of gasp-for-breath laughter and gasp-for-breath horror. A lifetime spent in the vicinity of a television screen led to his current dream job, as well as his knowledge of too many TV themes and ad jingles.