Showtime’s ‘Black Monday’ Is a Drug-fueled Look at the Biggest Stock Market Crash in History

Showtime’s ‘Black Monday’ focuses on the coked-up crimes of a bunch of debauched Wall Street brokers – and it's hilarious

Regina Hall as Dawn, Don Cheadle as Mo and Andrew Rannells as Blair in “Black Monday.” An exercise in excess and success.
Miller Mobley / Showtime

The coked-up crimes of a bunch of debauched Wall Street brokers may not sound like a promising elevator pitch for a comedy. True, movies like “The Wolf of Wall Street” have tackled the 1987 stock market crash – still the largest single-day collapse in share value in history – with humor. But one could be forgiven for having low expectations of a 30-minute sitcom featuring characters who display all of the worst characteristics of late-1980s’ piggish capitalism.

No one really knows what caused stock markets around the world to plummet on that October day 32 years ago; economists are still arguing about it. Showtime’s “Black Monday,” however, promises to reveal who was responsible for the crash and how it happened. It is, in the words of the promotional material, “the story of how a group of outsiders took on the blue-blood, old-boys club of Wall Street and ended up crashing the world’s largest financial system, a Lamborghini limousine, Don Henley’s birthday party and the glass ceiling.”

“Black Monday” stars Don Cheadle as Maurice “Mo” Monroe – the fast-talking, cocaine-hoovering CEO of the 11th-largest trading company on Wall Street. But Mo isn’t satisfied. On the morning of his 39th birthday, he gathers his staff and tells them that 11th-largest isn’t good enough. After all, he says, “The number 11 guy on the Knicks isn’t even a basketball player, all right? He’s an eight-foot Serb with a kidney disease they took a flier on.”

Mo wants change. “It’s been the same Monopoly-man-looking motherfuckers at the top of Wall Street for a thousand years,” he says. So he shares with his employees his plan, which involves buying out Georgina Jeans, which does all of its manufacturing in Manhattan. This, Mo says, makes the company ripe for a takeover.

Despite the objections of his de facto Number 2 – Dawn Darcy, played by the excellent Regina Hall – Mo sets his plan in action by buying Lehman Brothers’ shares in Georgina Jeans at an exorbitant price. In the first of many twists, however, it turns out that Georgina shares are the ‘white whale’ of Wall Street – countless traders have tried to buy a majority stake in the company, only to be foiled by the family that owns it, which keeps 51 percent of the stocks hidden to ensure no hostile takeovers are possible.

Enter Blair Pfaff – played by Andrew Rannells (“The Book of Mormon,” “Hamilton”) – a recent college graduate looking for his first job on Wall Street. Armed with an algorithm he believes can revolutionize trading, Pfaff also happens to be dating a scion of the family that owns Georgina Jeans.

Mo knows exactly who Pfaff is and offers him a deal: If he can use his algorithm to double an investment of $50,000 in the course of one trading day, he’ll employ him. Despite coming close, Pfaff’s algorithm displays some fatal flaws and he ends up losing all the money. But Mo’s plan – and the plot of “Black Monday” – is predicated on Pfaff’s unknowing complicity, so he hires him anyway.

Rare depth

“Black Monday” is packed with jokes that rely heavily on the period. When boasting about prolific drug consumption, Mo boasts that he has “freebased with the mayor of D.C.,” to which his colleagues respond with a chorus of “Mayor Barry!” Mo and Dawn argue over the merits of “Top Gun” and, in the second episode, Mo is shadowed by a screenwriter who is researching a film he’s working on, called “Untitled Oliver Stone Wall Street Project.” Stone’s “Wall Street” was released in December 1987. Some jokes are timeless: “You’re the worst trader in Manhattan since the Indians,” the Lehman brothers tell Mo.

It’s easy for comedies of this ilk to afford themselves the luxury of focusing on one or two main characters, while failing to flesh out the bit players. “Black Monday” almost does the opposite. Mo’s character, while hilarious – think Eddie Murphy’s stand-up meets Johnnie Cochran – is so far a little one-dimensional.

Three episodes into the show, we have not yet been allowed to see behind the mask; his backstory fluctuates like a volatile market and he is never candid about his plans. However, there is a rare depth to some of the supporting characters: there’s Keith (played by Paul Scheer), the married trader who can’t bring himself to leave his wife for his boyfriend; there’s Dawn, who, it turns out, is a highly educated woman from a respectable family, not the trash-talking, sassy trader she appeared to be.

“Black Monday” was created by Jordan Cahan and David Caspe, who also penned the first episode – which was directed by the kings of stoner comedy, Seth Rogen and Evan Goldberg. Their drug-inspired style is clearly evident throughout the episode – right from the moment, in the opening minutes, when somebody jumps from a great height and lands on the roof of the aforementioned Lamborghini.

Some of the jokes are a little close to the bone: Mo says that he’s the “Michael Jackson of dating. To clarify, I’m as good at dating as Michael Jackson is at dating kids” and Pfaff describes working for Mo by saying that, “You don’t really make Mo do stuff. He more sort of does stuff to you… like my gymnastics team doctor.”

Much like those heady, hedonistic days that preceded the crash, “Black Monday” is a drug-fueled exercise in excess and success. Those of us who were around at the time and who watched with pathological fascination as the Yuppies got their comeuppance will find in “Black Monday” a ruthless retelling of a period of recent history. Younger viewers may miss many of the cultural references of the time, and may be shocked by some of the debauchery depicted, but they’ll laugh at this hilarious exercise in historical fiction.