'Black Monday' Star Andrew Rannells Is Done Playing the Sassy Gay Best Friend

"I was excited to get to turn into a bad guy," the actor tells The Hollywood Reporter of his role in the Showtime comedy as an impressionable Wall Street recruit.
Erin Simkin/SHOWTIME
In the season premiere of Showtime’s Black Monday, there’s a spotlight moment for Andrew Rannells that crystallizes the show’s flavor of absurdist dark comedy. Having seen his bright future on Wall Street crushed in a single morning, Rannells’ rookie Blair Pfaff finally snaps and stands up to Maurice “Mo” Monroe (Don Cheadle), the impetuous trader who just tanked his career. “You think you scare me?” he explodes at Mo. “My dad beat me every day of my life until he died. He literally died of a heart attack while beating me.” It’s a startling non-sequitur that catches even Mo off-guard, and hints at psychological warfare to come.
 
“It’s a funny tone to play with, because it is very broad, and yet in other moments very grounded and human,” Rannells says. “That line is crazy, and the only way to say it is to truly believe it. I remember being like: well, I gotta really believe this! My dad died while beating me!”
 
Named after the day of 1987’s catastrophic stock market crash, Black Monday chronicles a highly fictionalized sequence of events leading up to the collapse. Unlike most “greed is good” stories, the comedy focuses not on the winners of Wall Street but on the underdogs: a scrappy second-tier firm named the Jammer Group headed by Mo. After years on the outside of the blue-blood, overwhelmingly white financial establishment, Mo is determined to break the top 10, and sees a way to do it by manipulating Blair. Fresh out of an MBA at Wharton, where he developed a trading algorithm that has made him a hot recruit on Wall Street, the book-smart Blair couldn’t be more out of place among coke-snorting, gleefully reckless traders. He also couldn’t be farther removed from Rannells’ breakout TV role, the acerbic, hard-partying Elijah Krantz on HBO's Girls — and that’s deliberate.
 
“I didn't want to jump into anything out of panic after Girls,” Rannells tells The Hollywood Reporter over coffee in Manhattan, a mile or two from Wall Street. “I was getting offered every gay best friend role in the world, and they were all the same. Sassy, kind of drunk …” In the interim, Rannells starred in two acclaimed Broadway shows — the musical revival Falsettos, for which he earned a Tony nomination, and a Ryan Murphy-produced production of The Boys in the Band alongside Zachary Quinto and Matt Bomer — and waited for the right TV opportunity to knock.
 
 
Black Monday had been in the works for close to a decade by the time it started coming together at Showtime, as Rannells was wrapping up the final season of Girls. One of the first general meetings Rannells ever had was with Seth Rogen, who exec produces Black Monday. “I met with him while I was still doing Book of Mormon,” Rannells recalls. “Over the years I would run into him, and we’d always say ‘We’re gonna work together, we’re gonna find something someday that'll be a fit for us,’ and then this was it.” Black Monday co-creators David Caspe and Jordan Cahan were also fans of Rannells from Girls, in particular his expanded role in the last season, and focused on him early on for the role of Blair. “He was just someone we loved,” Cahan says of the casting choice. “His character has an intense amount of growth in the season, and it felt to us like it would be a really fun, meaty thing for him to dig into.”
 
Much of the show’s early comedy comes from Blair’s fish-out-of-water naivety in contrast to the world around him. When he collides with Mo and causes a bag of cocaine to explode all over the trading floor, he can’t even identify the white powder (“What is this, parmesan?”) And at the end of the first episode, it’s revealed that Blair is in over his head more than viewers thought: Mo orchestrated this seemingly random collision to get Blair blacklisted, leaving him with no choice but to accept a job at the Jammer Group. Mo’s angling for a majority stake in a designer jeans company owned by the family of Blair’s girlfriend Tiff (Casey Wilson), and thinks he can use the unsuspecting Blair to get it.
 
“He comes in really thinking that he’s just gonna be able to work hard and be honest and will be rewarded for that,” Rannells says. In other words, it sounds like he’s going to be eaten alive. But Blair’s not a wide-eyed lamb to the slaughter, and it’s always clear in Rannells’ performance that underneath the pressed suits and Type-A energy, neurosis lurks. “He realizes, over time, that you do have to play the game and be manipulative. That, for Blair, is a real disappointment, and yet he takes to it. Once he figures out that's what he has to do, he gets right into it.” 
 
 
The 10-episode season will see a dramatic transformation in Blair, Rannells says, which was a draw for him. “That’s not something I get to do a lot. I was excited to get to turn into a bad guy.” Even early on, Rannells relished the strange, dark elements of Blair and Tiff’s marriage, which plays like a fully formed psychodrama in its own right. When Blair goes home dejected after his initial defeat, Tiff responds by smacking him in the face — twice — then gripping him very literally by the balls and ordering him back to Wall Street to make himself a success. “They have a very, very strange sexual relationship that borders on violent,” Rannells says, laughing a little at the memory. He and Wilson had worked together before on 2016’s Why Him? a movie heavy on improvisation. “Most of what we did was cut, because it wasn't really necessary to the story, but it was so much fun to do. We just fell into this weird vocabulary together.” Two years on, that vocabulary ended up informing their scenes in Black Monday, which Rannells says are more improvised than most of the show. “All the mommy and daddy talk, that was just nonsense that Casey and I came up with.” That twisted dynamic prevents Tiff, and their relationship, from feeling like a mere plot device in Mo’s scheme: “You can tell they really like each other, in that sick, sick way.”
 
This will be a busy year for Rannells. On top of his first regular series role since Girls, he has a book coming out, a collection of essays titled Too Much Is Not Enough: A Memoir of Fumbling Toward Adulthood. Chronicling Rannells' early years in New York after moving from Nebraska in 1997, the book sprung out of an essay published in The New York TimesModern Love column two years ago. “I've always wanted to do it, but I just never thought it would actually happen. I’ve always written things but sort of kept them private, so I'm nervous to actually get to share this.” The third major development for Rannells this year? Deleting Twitter. “I didn't really like how I was behaving,” he explains. “It was easy to just fire stuff off, in a way that seemed a little reckless. And then when it became the unofficial platform of our president, I was like, 'I don't think this is for me any more.’” He’s enjoying post-Twitter life, while acknowledging that it’s an option not all actors have. “I know on Girls, it was a big deal, they wanted us all on social media. But I just feel like it’s getting strange. I don't want to say anything flippantly that I can't back up later.”
 
Though Black Monday is Rannells’ first time playing a major onscreen character who isn’t gay, his sexuality has never felt like a defining factor in his roles. “The first gay part I really played was Elijah on Girls,” he points out. “Up to that point in theater, I was playing straight roles — Jersey Boys, Hairspray — because that's just what was available to me. Now, I get asked a lot if it’s limiting to play only gay roles, and it's only limiting if the writing is bad. I think people assume that there’s one gay type of person, and he's usually a girl's best friend.” And while the “gay best friend” offers are still coming, Rannells says he’s noticed a recent shift in the quality of writing for gay characters. “There are more human parts for gay people, and different parts, and it's not all the same type of guy. I’ve read a lot recently that’s exciting, stories that I’d like to be a part of telling in the future, and that’s encouraging.”
 
Black Monday airs Sundays on Showtime.