Jason Segel talks about taking on the daunting role of David Foster Wallace

'Day one, I was scared.'

David Foster Wallace’s thousand-page novel Infinite Jest is one of those books. It lives in the same class as Thomas Pynchon’s Gravity’s Rainbow or James Joyce’s Ulysses: books often bought as a rite of literary passage by ambitious readers who set out to conquer them as if scaling the hazardous North Ridge route up K2. The internet is full of fan-written readers’ guides, wikis, and other helping hands for getting through Wallace's dense vocabulary, the endless endnotes, and the heavy symbolism. But it’s a challenging read, and it’s purchased far more often than it’s completed.

So how do you make a movie about Wallace and Infinite Jest relatable to the average filmgoer? James Ponsoldt, director of the bittersweet YA-novel adaptation The Spectacular Now and the moving addiction drama Smashed, had a couple of key ideas: he and screenwriter Donald Margulies tackled David Lipsky’s non-fiction book Though Of Course You End Up Becoming Yourself, about Lipsky’s five-day interview with Wallace over the course of the last four stops on the Infinite Jest book tour. Wallace was frustrated with the immense literary fame the book brought him. Lipsky was hunting for a Rolling Stone story, and an angle on this reclusive, difficult-to-crack author. And while the film parallels Infinite Jest thematically, and comes with its own high-flying vocabulary, it winds up just being about two men dueling for control and struggling with the attempt to express themselves, and to get what they each want out of an unnatural and only fitfully satisfying situation. It’s a powerful but surprisingly enjoyable and accessible film, a surprise Sundance hit.

Segel's performance is the biggest revelation in a revelatory movie

Comic actor Jason Segel, best known for playing (and often scripting) hyperactive, sweet but stymied dorks in the likes of How I Met Your Mother, The Muppets, Freaks And Geeks, and Forgetting Sarah Marshall, wasn't an obvious choice to take on the complicated role of Wallace in the film. Early responses to set photos of him in Wallace regalia — the shaggy long hair, the scraggly stubble, the casual biker forehead-bandana — were harsh and dismissive. But he winds up being the biggest revelation in a revelatory movie. He's still distinctly Segel, in spite of taking on Wallace's rapidly shifting cadences and buck-a-word vocabulary, but he disappears into this role in a way he never has before, and he brings a strange inner intensity to a man mostly characterized by his laid-back surface and mild dubiousness about the entire interview process. Jesse Eisenberg, as Lipsky, pushes Wallace consistently throughout the film, but the burden of proof is on Segel, as he navigates Wallace's shifting feelings about Infinite Jest, about how he's living out the book's themes, and about whether he even wants the conversation to continue. I recently spoke to Segel about his anxiety over the role, and how life and art complicated each other significantly around the film.

Tasha Robinson: You've said the test of this movie is going to be how well it connects with people. But given that it's about such a specific situation, between two very distinctive, idiosyncratic people, what do you see as the larger issues where people can see themselves in this story?

Jason Segel: I think for me, it's the themes of two [books]: Infinite Jest and This Is Water. I think they tie together, and I think you can feel that in This Is Water, which was written 10 years later, David Foster Wallace had worked through these themes a little better. It's all about this scary moment where you realize that [you've done] what you've been told is going to make you feel satisfied. Everything goes the way it's supposed to. But you're left feeling empty. The itch is still there. That's the SOS that's being sent out in Infinite Jest, as I read it. I felt like I was listening to a guy say, "Hey, I feel dissatisfied, does anyone else want to join me in this conversation?" And then you read This Is Water, and I feel like it's a guy who's worked through that idea a little further, and is saying, "Look, I'm no expert, and I'm still trying to figure this out myself, but it seems to me like maybe the solution is where we place our value. And as opposed to putting it in success, or money, or beauty, we should put it in connection. Connection with each other, connection with some sort of higher power." But what I hope resonates with the movie is this conversation, which is, "Maybe we need to refocus our energy if we want to feel satisfied."

You did a book club with Infinite Jest with some friends, studying it and discussing it together. What did you get out of that process, in terms of understanding these themes?

What really was interesting to me was — the book is three prongs. There's a recovery house in Boston, so that one is endeavor. There's a tennis academy, and that's achievement. And then the third is about an entertainment that's so pleasurable, it zombifies the viewer. So you've got pleasure, achievement, and entertainment, and in all three of those pursuits, people are left feeling dissatisfied. Numb. Confused. And in reading it with three other guys around my age, it was interesting that different people strongly identify with one of those elements, because it's reflective of where they've placed their bets. And to have four grown men sit around on a Sunday and end up talking pretty candidly about feelings of dissatisfaction, I think really spoke to the kind of author David Foster Wallace is. I can't think of another experience I've had like that, except maybe Catcher In The Rye in high school.

How do you use all these big ideas to find the character of the author — or at least, how he should play onscreen?

I think especially in this circumstance, one of the big poles of the dynamic between Wallace and Lipsky is, Wallace is going through this moment in real time. The movie takes place over the last four days of the Infinite Jest book tour, so it is happening. Things have gone as well as they can possibly go, and Wallace still feels the same. He has very complicated feelings, but he doesn't feel the way he hoped and dreamed he would. And you get the sense that he would really like to talk about that with Lipsky. He keeps trying to open that conversation, and Lipsky is just so concerned with his own agenda that he can't see it. In effect, he calls Wallace a liar several times: "Stop putting up this aw-shucks façade." And Wallace is saying, "If you would just listen to me, I have the real story for you right now, kid."

This is being heralded as a radically different role for you, a big career move in terms of depth and drama. Did it feel that different to you? Did you have to approach it differently from other roles?

Yeah, if I'm to be perfectly honest about it — it sounds like a joke, but it's really true. I think having written a lot of what I've done before, I had never had to do prep the way I did prep for this. I'd never played a real person. I'd never had to sit and try to think about exactly what I meant by each thing I was saying, because normally, I had written it. And so honestly, what I tried to do was picture what an actor I admired would do, and I copied that. And that is the absolute truth. I imagined what somebody would do if they were given this part, and then I did all of those things.

Who did you have in mind? Was this a "What would Meryl Streep do?" kind of process?

It was all in that wheelhouse. But I think anyone I bring up would sound comparative, and that's the last thing I want to do. It's tough in print to get tone across. But all of the actors I admired growing up — there are some actors out there where you can't sense any self-satisfaction behind their acting, and that's what I really respond to.

You've said the script was so good, it made you feel safe with the film but anxious about whether you were up to the material. Did that anxiety fade in prep? During filming? Was there a point where you came to a comfort with the material?

I became comfortable on the second day of shooting. There was no way to feel comfortable in prep, because there was no rehearsal process. There just wasn't the opportunity for the real moment where I walked out in full costume, doing the full dialect, the speech pattern. And I hadn't acted against Jesse yet. So day one, I was scared. And luckily, that worked, because it was the scene where Jesse and I meet for the first time, and I think David Foster Wallace is anxious in that moment. I think that translates. Day two, we shot the final scenes in the house, between us. We shot the big [confrontation] scenes at the end. And so that was a real trial-by-fire day. By the time that was done, there was some feeling of, "Well, you've shot the big scenes now. So if you messed those up, there's nothing you can do!" So it got a little easier at that point, because I was just in the moment. Honestly, this whole movie is me trying to listen to Jesse.

The End of the Tour


Like Lipsky and Wallace, the two of you didn't know each other at the beginning of production, and you shot largely in sequence. How did that play on your end? Did you avoid spending time together off set, to keep from getting out of sync with the material?

No, quite the opposite, actually. It was a really unique experience. It was negative-15 degrees in Grand Rapids, Michigan. I don't know if you have experience with that kind of weather, but there's forced intimacy about it. Like, the windows are always rolled up in the car. You're really forced to talk to each other in a tight-space kind of way. So we drove to work together every morning, and would act together all day, and then drove home together at night, and we would talk about what we had shot, or basketball, or what was going on in our lives. The whole process, there was a life-imitating-art thing going on. I'm just a few years older than Jesse. We were both in big transition periods in our life and career. So we had a lot to talk about, and a lot of it circled these themes.

How did you keep the dialogue loose and natural? You said James Ponsoldt didn't have a rehearsal process. Was that to keep the dialogue from getting too rote with repetition?

It wasn't that he wasn't interested in rehearsal, it's just that scheduling made it impossible. I was doing [How I Met Your Mother] in Los Angeles up until the day before I started shooting. I wrapped the TV show on a Friday, and flew out and started my first day of shooting on Monday. So there just wasn't any time for rehearsal. But James said, "If this was a movie about two roommates, or best friends, or brothers, it would be necessary." But for this, it worked, because you can feel us sniffing each other out on camera. I think it works well. There's a Frost/Nixon element to this movie that's driving a lot of the tension.

Marshall on How I Met Your Mother is a very different character from Wallace, but several of your best-known characters have this shared sense of a surface affability hiding a deep core of resentment or anger, and often the stories are about them figuring out how and when to access it. Do you feel any sense of connection there?

I know what you're talking about, but I think in a lot of the characters I play, instead of anger bubbling beneath, it's sadness and insecurity. They never really get angry. Some of them have been about people dealing with deep-seated insecurity, which is an area that's always really interested me. But again, having written a lot of what I've done ... In my 30s, I'm just thinking about different stuff. I'm at a different place in my life. Where I was when we shot this was very similar to one of the lines Wallace says in the movie: "I have to face the reality that right now, I'm 34 years old, alone in a room with a piece of paper." And that's very much how I felt when we were shooting. The TV show had just ended after almost a decade. I was feeling like I wanted to do something other than what I was previously successful doing. So there was a big part of me that just felt like, "What now?" That I'm basically having to start from scratch. And I think that's how Wallace was feeling in that moment. He writes a thousand-page book, and... I know what a press tour is like, I've done a bunch of them. I guarantee you that on the Infinite Jest press tour, they're asking him, "What's next?"

The End of the Tour


Would you say this kind of film is what you want out of the next phase of your career?

Yeah, I think what I want out of the next phase of my career is to continue to do things that scare me. I don't feel limited by any genre, or anything like that. I just want to be constantly exploring my limits.

What was the last role before this that scared you?

Jeff Who Lives At Home, which was a few years ago. The Muppets scared me for other reasons, just because I love the Muppets so much, I really didn't want to mess it up. But Jeff Who Lives At Home was something where I was equally scared going in.

"I want to continue to do things that scare me."

Speaking of anxieties, the speculation about this film during its production was fairly negative, much of it to do with your casting as Wallace. There seemed to be a feeling that the image of you dressed in Wallace's idiosyncratic style was automatically comical. Were you concerned about that perception?

No, I stopped looking at the internet a long time ago. Honestly, when I found out I was going to be playing this part, I had better uses of my time than to manage other people's fear about the movie. I had my own fear to deal with. I think the whole beginning process of digging into this was me figuring out how to proceed unapologetically. If you could sniff out that I wasn't sure, why should anyone else be sure? If I didn't believe it, why should anyone else believe it? So I spent a little time — I didn't overindulge in it, but I spent some time coming to believe I was the best person to do this. Or at the very least, that I was the one hired.