Inside ‘Fleishman Is In Trouble’ with Claire Danes and Jesse Eisenberg

Fleishman Is In Trouble
Jesse Eisenberg as Toby Fleishman and Lizzy Caplan as Libby Epstein in ‘Fleishman Is In Trouble’ (Photo CR: Linda Kallerus/FX)

Fleishman Is In Trouble author Taffy Brodesser-Akner says one of the biggest challenges in adapting her book for the FX on Hulu limited series was learning to write dialogue rather than lengthy paragraphs. Fortunately, Brodesser-Akner’s a quick learner and had the support of experienced executive producers Sarah Timberman and Susannah Grant while working on her first show.

“When I met Sarah and Susannah, they told me that I was the only person who could write it, and I’m like, ‘Yeah, what if I’m the only person who could write it?’” recalled Brodesser-Akner during a November 2022 press conference. “And that’s how I got to do it, with two people who believed in it and who showed me how you could change just a few words and change the nature of an entire scene.”

Showrunner, writer, and executive producer Brodesser-Akner joked that next she’s thinking of going into casting after snagging her first choices for the lead roles. Oscar nominee Jesse Eisenberg (The Social Network) stars as Toby Fleishman, three-time Emmy winner Claire Danes (Homeland) plays Rachel Fleishman, Emmy nominee Lizzy Caplan (Masters of Sex) is Libby Epstein, and Adam Brody (Single Parents) stars as Seth Morris. (The four leads joined Brodesser-Akner for the lengthy press conference.)

“I have to say that these are the only people I ever pictured for this role. I think that the roles are so specific. I can’t understand why these were the only people that occurred to me,” said Brodesser-Akner. “I think that these people together…I mean from the minute they were together – some of them knew each other before we started, some of them did not – and now when I watch Lizzy and Jesse and Adam together, I feel that they have been friends for life. When I watch Claire and Jesse together, I feel that they’ve been married, and it’s funny to be in a situation like this where I see them be friends after months of watching acrimony on screen. It’s extraordinary.”

According to Lizzy Caplan, the friendship vibe was there from the beginning of production.

“That was one of the things that I loved so much about being a part of this is showing this friendship which felt so familiar to me that it was – I mean from the first scene, we didn’t even have to ease into it. We were just kind of there. And I think that’s a combination of all of us doing this for so long, we could probably fake a friendship with whoever at this point, but for it to feel this authentic, the rarity of it, it just made it instantly fun,” said Caplan.

The series focuses on the shattered marriage of Toby (Jesse Eisenberg) and Rachel Fleishman (Claire Danes), and how Toby attempts to sort out his life as a newly single father of two. Lizzy Caplan and Adam Brody play Toby’s supportive friends, Libby and Seth, who he uses as sounding boards as he eases back into single life while struggling to understand how he got to this point.

Rachel’s sudden disappearance further throws a monkey wrench into Toby’s life as he’s forced to consider what transpired in their marriage that left them both such broken people.

Toby hadn’t been able to spend much time with his friends before the end of his marriage, and reconnecting has its own unique issues.

“The interesting thing for my character is that the reason we get back together is because I’m going through this horrible experience, and so I’m dipping my toes back into my past, but I really have one foot outside the door of the relationship because I’m so self-involved because I’m doing through this, you know, horribly fraught divorce. And so, it’s kind of an interesting way to backtrack into an old relationship, kind of not in the most responsible (way) – not as a complete, committed friend, but as somebody who really needs people at this horrible moment,” explained Jesse Eisenberg.

There’s a sense of loneliness that permeates each of the four main characters. The actors embraced and empathized with that aspect of their characters.

“I’ve only ever felt alone in a crowded room. And alone in rooms alone,” joked Eisenberg. “The whole show did feel like, at once, very specific, culturally and comically and dramatically, but also I felt when I had read it – the same feeling when I read the book – which was that this is something that feels so culturally specific to something I know very well, and I’m familiar with and grew up in, but at the same time, probably accessible to somebody who grew up in a completely different set of circumstances. That’s the kind of beauty of the show and the book.”

Adam Brody believes that rather than loneliness, there’s a melancholy to the show and book.

“I feel that about life, and I feel like as you get older and you’re in your 40s, you’re still asking the questions about who you are and where you want to go, and you’re still at a crossroads,” offered Adam Brody. “You still have a lot of lessons to learn, things to discover, and it’s not just for people in their 20s.”

Lizzy Caplan suggested there’s a specific kind of loneliness that occurs in a marriage. It’s unexpected and jarring, and accepting it can be difficult.

“I think there’s this unspoken thing that people say to themselves, like, ‘I’m never going to feel lonely again. I have this person. I have my person. And then a family.’ And so, when you start to feel those feelings of loneliness or alienation within your household or your family unit, it’s even more destabilizing because it’s like somebody’s reneging on the promise,” said Caplan.

She added: “There’s so many things in the show, in the book, that I love so much, but the idea that when the person closest to you, your husband, in Libby’s case, it’s very easy to point your finger at him when the rest of your life isn’t going the way that you envisioned it going because he was there for all of it. So, it’s very easy to blame him. I think you say he’s like a comorbidity to the rest of your life not working out. And the sad truth theme of this whole thing is that even if you divorce your husband, you’re not going to be 22, and you’re not going to get a do-over.

So, it’s facing down all of that, which is what it is to be in your 40s. And I certainly didn’t think I was going to be facing that down in my 20s. It’s like the thought doesn’t even occur to you until you’re in it.”

Fleishman Is In Trouble Claire Danes
Claire Danes as Rachel Fleishman in ‘Fleishman Is In Trouble’ (Photo CR: Matthias Clamer/FX)

Claire Danes loved exploring the Fleishmans’ marriage as well as the relationships that surrounded it.

“I think it does kind of tease at a huge fear that I think we all share, which is how well do you truly know your most intimate partner? And how well do you know yourself? And sometimes, the answer is confronting, right, not very,” said Danes. “I think that anxiety about that potential alienation within very close proximity is spooky. And tragic, right? But they’re all wrestling with the big stuff and have to go through their little crucibles and go through a lot of discomfort. But, you know, maybe at the end, they’re a little closer to their truth with themselves and each other. And therefore, a little closer to each other.”

Jesse Eisenberg found it interesting that his and Claire Danes’ characters were viewed from each other’s perspectives.

“So, when Claire is viewed from my perspective, she appears ambitious to a fault, vindictive, negligent, and then when the show flips perspectives and you see me from her point of view, you have similar feelings towards me,” explained Eisenberg. “And so, one of the challenges that we faced was just kind of modulating how villainous and how heroic we are as actors. Goodness, (how) sympathetic to make our characters, or how kind of aloof to create our characters when you’re in the perspective, the other person’s perspective – that was kind of a very interesting challenge. Sometimes, we would simultaneously do scenes from different perspectives and have to kind of make these small modulations to try to have that effect.”

The process of preparing to play this married couple with seemingly unsurmountable issues included playing dodgeball. Yes, you read that right. Dodgeball.

“We all had a couple of dinners, which are very helpful, truly. Just getting a sense of each other and breaking bread literally and developing a teeny, tiny bit of trust, and we had a couple of rehearsals, really only a couple. They were very brief, but they were effective. They were dense, and Jon (Dayton) and Val (Faris), our directors, had a really interesting approach,” said Danes. “They had us do some writing exercises and asked, like gave us these pretty provocative prompts, and we played a game of dodgeball, for reals.”

Danes continued: “They wanted to physicalize that sense of combativeness, right? And we had a rehearsal with our children, and that was all pretty helpful, and it did kind of shoehorn us into the actual, the real stuff of filming.

I can’t speak for Jesse exactly, but I felt very fortunate just to have a kind of immediate, natural affiliation and connection and rapport. I think we both love the story and both love the language…and we have a lot of it. We spar a huge amount and I know it was contentious, but it was actually kind of joyful.”

Fleishman Is In Trouble premieres on Hulu on Thursday, November 17, 2022.