‘Fleishman Is in Trouble’ Is a Trojan Horse for Women’s Stories, Says Lizzy Caplan

At first glance, the series Fleishman is in Trouble seems to be a story about a divorced dad (Jesse Eisenberg) navigating single parenthood and the mid-life dating scene. But right away there’s a clue that things are not as straightforward as they seem: The series is narrated not by Toby Fleishman, but his old college friend, Libby, played by Lizzy Caplan.

Caplan likens the series, which is based on the novel by showrunner Taffy Brodesser-Akner, to a Trojan horse: “You think that you’re watching this story about a man getting divorced, figuring out dating apps, and you’re really not watching that story at all.”

Over the course of the series’ eight episodes, the story shifts its focus, so that by the end, in addition to seeing things from Toby’s point of view, we also hear from Libby and from Toby’s ex-wife Rachel, played by Claire Danes. Caplan says the structuring was deliberate.

“It’s a sad truth … which is: I don’t know if this show would have been watched by as many people if it was about a woman [Rachel] going through horrific postpartum depression and anxiety, and another woman [Libby] having sort of a slower burn mid-life crisis,” Caplan says. “I think that immediately turns off a lot of male viewers and honestly, a lot of female viewers as well.”

Caplan’s first acting job ever was in the 1999 high school drama, Freaks and Geeks. More recently she was nominated for an Emmy for her role as a sex researcher in the Showtime series, Masters of Sex. Libby, her character on Fleishman is in Trouble, is a former magazine writer who’s become a suburban stay-at-home mom. Libby’s struggling with marriage, motherhood and identity — and mourning the loss of her own youth and potential. Caplan began shooting Fleishman shortly after becoming a mother herself, which made Libby’s struggles even more resonant.

“It was just a lucky break to get to do this show at the dawn of my own motherhood,” she says. “The curtain was being ripped away on a daily basis for me, especially in those first three months, as I think it is for many new mothers.”

Interview Highlights

On being stuck auditioning for the same female archetypes earlier in her career

I feel like the roles for women, especially in television, they just get more interesting … as I’ve gotten older. But I know that is certainly not something that everybody feels. I know that I’m lucky to feel that way. But I definitely remember when I was younger and auditioning for a lot of this high school stuff or some early-twenties stuff and the male roles were always better. They always got to do the more fun stuff. And you were sort of relegated to a few different archetypes as a girl, especially back then. It has changed a lot, I see. A lot of the teen shows now, there is a shift, but there was the hot popular girl, there was the nerd. There was, like, the alternative best friend, which was very much my lane for a while. And I was very fortunate to be in some projects that kind of skewered the archetypal nature of those things. But for the most part, the things I auditioned for, certainly I remember asking many times when I was younger, like, “Can I audition for the guy part? Is there any way? There’s no reason why this character has to be a guy. It can be a girl.” And I certainly had nowhere near enough clout in the business for anybody to do anything other than laugh at that request.

On losing her mother when she was 13 and turning to acting in her grief

I had no idea how to process my mother’s death. It took me many, many years, but I knew that it gave me a darkness that in my mind was a requirement for being an actor, or the kind of actor I wanted to be. I needed to have this inner pain in order to do it. I remember going to an acting class and auditing it when I was 16 years old, and it was in Hollywood. It was a pretty prestigious acting class and it was full of 100 people in it and it went really late, till 1:00 a.m. And I stayed there and I watched it the whole time. And then I met with the teacher afterwards to see if I could join the class. And she looked at me and asked me how old I was, and I said I was 16. And she said, “You haven’t had any life experience. You can’t be in this class,” and booted me out. And that moment, it’s so crystallized in my brain because I remember feeling like, ‘Oh, no, this is the community that’s supposed to see these things in me — that I do have the depth that is required to be in this class — but you just see some dumb little teenager who hasn’t been through anything.’ When the reality was I had been through what is still the most monumental tragedy of my life.

On her first role in the series Freaks and Geeks

Little did I know that “critically acclaimed and short-lived” would describe the vast majority of my future projects. The experience itself was very overwhelming … just stepping into this completely different universe that I had no idea about. I grew up in L.A., but I had never been on a movie set before. I didn’t know how any of it worked. I didn’t know about marks on the ground and coverage and close ups and how long everything was going to take and hair and makeup and how many outfits I’d have to try on for this one line that I was going to say.

I remember … just looking in the mirror for hours, just reciting this one line over and over and over and over again and being terrified and just in love with the idea of this moving village with these hundreds of people all working towards this goal together, but also feeling, again, completely overwhelmed, very shy, not bonding in any way with any of my castmates or anybody. I look back at that experience and it was just honestly pure luck to end up on a show that ended up being so loved and so respected for so many years, because I really did audition for all kinds of nonsense, and just that was the first place that picked me. But it wasn’t a fun experience for me. It was mostly just scary.

On her break-out role in 2004’s Mean Girls as “alternative” girl Janis Ian

All I knew was that it was the funniest script I had ever read and I would do anything to be in it. And then the making of that was so fun. We were in Toronto and young and living in this hotel together, and it was just a wonderful experience. And then it did well when it first opened. And so I thought that meant that I was off to the races. And that is certainly not what happened. I didn’t work after that for a year. I didn’t really understand how I could be in something that seemed to be successful and none of that success seemed to be rubbing off on me. So I did what most actresses in the early aughts did and got a spray tan and dyed my hair blond and just joined a show [Related] on the WB network. That felt like the antidote.

On relating to the characters in the 2009 Starz sitcom Party Down, which was about struggling actors working as catering servers

I remember very vividly catering the Being John Malkovich premiere party and walking around with a tray of passed apps and none of these people looking me in the eye at all. I was just, like, a tray that moved, and feeling those feelings that all the characters in Party Down were feeling, which was basically like, “Oh, you don’t know who I am now, but you just wait!” I actually think there’s like two schools of thought for actors: One, when you’re starting to come up, one group takes rejection and internalizes it and believes it to be true. All the things that they say about them, that they’re not funny enough, pretty enough, whatever. And then the other school, the other group feels like, this is just ammo for me and this is just fueling my inner fire and I’m going to prove all of you guys wrong and you just wait and see! And like I, for whatever reason, fell into the second group and every rejection, I like to imagine it making me stronger and angrier and more determined.

On how filming sex scenes has changed so much now with intimacy coordinators

So much [has changed]. Which is wonderful, especially for the young people starting out, for the young actresses that don’t yet feel powerful enough to speak up on set, because it’s a very intimidating place to be when you’re young and new. So [with my first time doing a sex scene in] True Blood, it would never happen like that again now, where I was just, like, drinking vodka at 7:00 in the morning to try to build up the courage to do this. And they were wonderful on that set. I’m very, very fortunate. I never found myself in a situation doing any of these jobs where I felt unsafe or pressured into anything. And so I’m not really even the person the intimacy coordinator is there for. They’re there for the people that are having a very different experience. Masters of Sex, definitely no intimacy coordinator. And it’s like a completely different time because since then I have worked on shows where there have been intimacy coordinators and there’s this whole other step that just didn’t exist at all back then.

On starring in a reimagining of the 1987 film Fatal Attraction (coming April 2023 on Paramount+)

It’s important to note that I love the movie Fatal Attraction. I think it’s wonderful. I think it holds up in so many ways. It’s still scary. It’s still exciting. It’s still very sexy. The performances are incredible. It looks beautiful. I love the film. But when you watch even the film now, I find, as an audience member, it’s really difficult to see it in the same way that audiences saw it in 1987.

In 1987, you go to a movie about a married man, who’s married with a child who has this torrid weekend-long affair, [and] everything obviously goes haywire. [The other woman] becomes obsessed with him and we walk away feeling like that woman was evil, horrible, despicable, deserved to die. This poor man who made this one little mistake deserves nothing more than to ride off into the sunset with his wife and child. Thank God he prevailed against this horrible woman!

When you watch it now, it’s very difficult to not have some follow up questions about that. That version of the film can’t exist in 2023 because of these questions, because we’re now primed as audiences to want to know more about the woman, where she was coming from, and also to place some very well-deserved blame on the man. There’s no blame placed on him in the film. So I think while I completely understand wanting to preserve things that meant a lot to us as audience members, like the holiness of a movie you loved growing up, there are other ones like Fatal Attraction where I think, Why not? Let’s do a deeper dive into this, because there are now more questions when you rewatch it. And if nothing else, I really think that it holds a magnifying glass up to audiences and how much we’ve changed, that a movie like that was so hugely commercially successful as well as critically acclaimed and awards … audiences today can’t see it through that same prism anymore. We just have changed so much as a culture.