Jason Segel on playing David Foster Wallace: "I'm starting to think the things we've been told will make us feel good are a lie"

How the star of "Sex Tape" took on the Gen-X literary godhead -- in a movie the Wallace estate tried to kill

By Andrew O'Hehir

Executive Editor

Published July 29, 2015 11:00PM (EDT)

Jason Segel as David Foster Wallace in "The End of the Tour"     (A24)
Jason Segel as David Foster Wallace in "The End of the Tour" (A24)

Did I feel like I was being played by Jason Segel, who has spent much of this week holding earnest conversations with journalists in the lobby bar of the Bowery Hotel in downtown Manhattan? I mean, sure. I didn’t mind too much. Any interview with an actor involves an element of performance, and this was a pretty solid one. (Segel didn’t ask me to help me rearrange the pictures on the walls of his hotel room, and then deride me for my command of Spanish and my perceived lack of outdoorsy knowledge, as Tommy Lee Jones once did.) When the actor in question is talking about playing a highly self-aware literary genius who was always asking questions about artifice and authenticity – in a movie that is itself about the awkward dynamics and ethics of the interview process – then the performance demands expert calibration.

At age 35, Segel has reached an obvious inflection point in his career, and you can’t say he hasn’t gone large. After spending 10 seasons playing Uncle Marshall in the CBS sitcom “How I Met Your Mother,” and writing and starring in a series of downwardly successful Judd Apatow-style Hollywood comedies, it’s not surprising that Segel wanted to take on a serious dramatic role. Actors love to talk about “risk,” and the risks of playing the late novelist and generational icon David Foster Wallace in James Ponsoldt’s “The End of the Tour” -- a movie the Wallace estate did its best to prevent from happening – were almost off the charts. Wallace fans heaped social-media derision on Segel as soon as the casting choice was announced, and the potential for either an exploitative wallow in the past of a famous suicide or a tedious hagiography (or maybe, somehow, both) was evident.

As Segel suggested in our conversation, people who spent a lot of time on the Internet hating a performance that had not happened in a film that did not exist perhaps hadn’t thought too deeply about the issues raised by David Foster Wallace, who was no snob. On the other hand, the bizarre media cycle around this movie almost certainly paid off for Segel in the end: When Ponsoldt’s film premiered at Sundance and was universally greeted as non-terrible, Segel’s shaggy, boyish, alternately seductive and evasive performance as Wallace became a signifier of artistic courage and resilience, both a comeback narrative and a career turnaround. Segel’s conversations this week on the tasteful leather sofas of the Bowery Hotel – I found myself unsure whether Wallace would have loved the dim, moneyed, ersatz-vintage flavor of the place or loathed it – represented the opening gambit in an Oscar campaign that has to not feel too much like an Oscar campaign.

“The End of the Tour” is essentially a two-hander for Segel and Jesse Eisenberg, who plays a young journalist and novelist named David Lipsky, who in 1996 wangled a Rolling Stone assignment to spend several days with Wallace during the final leg of his publicity tour for his doorstop masterpiece “Infinite Jest.” Lipsky’s feature never saw print in Rolling Stone (for reasons not directly discussed in the film, but perhaps apparent) but years later, after Wallace’s death in 2008, Lipsky hauled the hours of tapes out of the closet and turned them into a book called “Although of Course You End Up Becoming Yourself: A Road Trip With David Foster Wallace.” (Wallace’s estate had no power to stop that book, or this movie, because the tapes were Lipsky’s property, and because dead people have no right to privacy.)

I want to let Segel’s performance during our interview speak for itself, as does his performance in this thorny, talky, frustrating and intriguing film. Let’s say this: In both contexts he is really trying to ask himself difficult questions and ramp up the challenge. In “The End of the Tour,” Segel tries to create a likable and believable fictional character who is also driven by the immense cultural and philosophical switchbacks of “Infinite Jest,” the defining masterpiece of American postmodern literature. (There are most definitely still haters amid the early Oscar hoopla: In a Guardian essay that has sparked considerable discussion, critic Glenn Kenny, who knew Wallace, has called Segel’s performance “ghoulish self-aggrandizement.”)

During our conversation, Segel sprawled his 6-foot-4 frame all over that leather sofa in various postures of cogitation and self-interrogation, making eye contact and then retreating, deflecting the questions that made him uncomfortable and then apologizing and working his way back to them. As I understood it, he conveyed that he knew I knew this was a performance, but that if there was any genuine lesson to be drawn from the life and work of David Foster Wallace, it lies in understanding that every performance contains something real.

It’s funny to get here right after a big New York Times article about you, which has the effect of framing the story whether we want it to or not. I mean, now everyone has read this thing that says, oh, Jason Segel has reinvented himself, it’s a career U-turn! Well, how interesting! Do you look at something like that and have the feeling that it’s about somebody else?

My most honest answer to that is I don’t look at any of that stuff. It was a decision I made a long time ago. Honestly, entertainment news has a lot of gray areas. Even on Salon.com! [Laughter.] On the same website you will see a thing that seems legitimate next to an optional click that says “10 celebrities with fat spouses.” I just realized at one point that it would be better for me to not look at this stuff. That being said, it means a lot to me that people are psyched to see somebody do a good job. That’s a really nice thing, whether it is me or anybody.

That sounds like a good plan, but it must be hard to stick with that. The only thing that comes up as a journalist that’s anything like that is when you get a lot of either hostile or positive feedback, and that becomes really addictive really fast if you permit it to. You’re talking about attention on a much larger scale than that. You must have to be disciplined to avoid it.

I get asked a lot in these interviews, “How did you feel about people’s reaction when you were cast in this movie?” My answer is I had no response to criticism of the hypothetical performance I haven’t given yet. My version of action is impossible. There’s no solution to that idea. It’s finding a real solution to an imaginary problem. I try to focus on what is going on actually in my life. To answer that question, how I felt when I was first cast – not that you asked me that –

Go for it. I was definitely going to.

My honest answer is I was really scared about what was actually happening, that I had agreed to take this part. The best use of my time at that moment was not to be looking at the Internet, but to be reading David Foster Wallace as much as I could and working as hard as I could at that performance, so that by the time I arrived there I could proceed unapologetically. If I didn’t believe in what I was doing, why was anybody else going to believe it? I think I zeroed in on that. I have plenty of actual stuff to think about and worry about.

What’s the difference in responsibility, as an actor, between playing a fictional character invented by a screenwriter, whether or not drawn from real life, and playing a real person who was recently alive and who was known and admired and loved by many living people? Does that change the equation?

It does for me. That’s how I’m built. I wanted to proceed with a great deal of empathy and respect for the fact that there are a lot of people who love David Foster Wallace. The way I felt would be best to honor that idea was to make sure I really understood the themes I thought he was trying to express in “Infinite Jest,” and to make sure that this performance was an expression of that, versus some deification of David Foster Wallace that would be inaccurate and not true to the very themes that he tried to express.

I’m also really familiar with the press tour by the nature of having done a bunch of movies. One of the things that I zeroed in on-- there’s so much abstract thought behind this, I’m serious. I’m different on this press tour than I am doing a press tour for “The Muppets.” Neither of them is a lie. They are both reflections of what I am thinking about all day for two months. It affects what is at the front of your brain. I was aware that this was the last four days of a long book tour. Likely, if he was anything like me -- which is a premise I had to adopt first, that we are all the same -- then what was at the front of his brain were the themes of “Infinite Jest.” That’s what he’s been thinking about, talking about, and writing about for X number of years.

I really tried to home in on those themes and those seemed to me to be, when I read it, I felt like, an SOS being sent out by David Foster Wallace saying, “Hey. I’m starting to think the things we’ve been told are going to make us feel good are a lie. Does anybody else feel this way? And if so, will you please join me in this conversation?” Then when I started approaching the actual material, the actual words I was going to say, I tried to make it all that by trying to start a conversation with Lipsky, that Lipsky refuses to engage in. It’s that horrible phenomenon when you are having a conversation with a contrarian and they keep disagreeing with you in the lead-up to your point. You never get to get to your point.

That’s what the whole four days [of the Lipsky-Wallace road trip] felt like to me. A guy who was actually really hoping to have this conversation and another guy who came in with such an agenda that he never allows it to happen. I feel really bad for Lipsky at the end of the movie and I think that’s why the climax in the movie to me is when I leave and Lipsky is left alone in the house and finds that St. Ignatius quote on the wall. It’s a moment where he is like, “Oh shit, I’ve been calling this guy a liar and maybe he wasn’t lying and I missed the real story.” I didn’t even know that was the climax of the movie until I saw it for the first time with [director] James Ponsoldt. I thought the climax of the movie was when I go into the room and give my last speech to him about suicide and I walk out. It happened and I thought it was good, but then I was like, “Maybe I would like a little more, to feel something more.” Then I leave and Lipsky goes through the house, and Ponsoldt finds this moment that is just incredibly moving.

Any time I’ve ever thought about directing I think to myself, “Yeah but directing is an actual skill and passion.” That was confirmed for me when I worked with Ponsoldt, with moments like that. I didn’t even see that. I was like, “Oh. You stay on Jesse’s eyes there while I’m talking? Oh, right -- because now that changed what happened. That was the whole point of the scene.” I’m not built that way.

This is a funny thing to say, but I really felt for Jesse Eisenberg, playing a guy who is so defensive the whole time and who constantly deflects the conversation in ways the audience doesn’t want him to. He’s playing someone who is way more messed up and confused than the subject of the interview, and who arguably has no idea what he’s doing.

Jesse is just not afraid. He’s completely unapologetic. There are so many times you are so frustrated with Lipsky, but because of this quality that Jesse has you just don’t hate him. Or anyway I didn’t. As a matter of fact, I zeroed in, a week into shooting, on this idea of having a conversation with your younger self. You’re allowed to yell at them, but you also feel a tremendous empathy because you know they’re on a journey, they are becoming you. That’s how I felt, acting with Jesse. He was playing David Foster Wallace pre-accomplishment, when he was all ambition.

How did it change the process as an actor that you had all this material, all this recorded verbatim conversation? That has to be weird. How did you deal with that without just trying to imitate the inflections and replicate what you could hear on the tapes?

One of the things that was helpful -- the dialogue all comes from the interviews, but it’s been curated by [screenwriter] Donald Margulies. Not everything is said at the same time or in the way that it was said originally. One of the pitfalls of the movie, potentially, is that it is two smart guys saying smart things back and forth, which is not a movie I want to see. It had to feel like a conversation and you had to know the words, but also understand what you were trying to say so well that they seemed like spontaneous thoughts.

The challenge, which I have never seen before, is that David Foster Wallace could speak in fully constructed arguments off the cuff with a thesis, supporting points, and a conclusion. When I watched him on Charlie Rose and stuff, it was interesting. You could see the way he talks with his hands, moving information around. It reminded me of “Minority Report.” [Laughter.] A guy who had all the information at his disposal. You could see him writing, literally, in space. These are all things that helped me be normal on screen. That’s what I zeroed in on. He’s a guy who has all the information and vocabulary at his disposal, and is now going to construct an argument while he speaks to you. That’s why his language is also rhythmic. He’s something like a conductor. He’s conducting language.

So much of what Wallace talks about, in his conversation with Lipsky and in his work more generally, are the dangers of fame and all the forms of falseness or affectation that can arise from that. And, I mean, you’re a movie actor. Was that meaningful for you on any personal level?

I was at a time of real transition. I don’t mean just professionally, or just in the sense that this is a drama rather than a comedy. I mean there was a lot that was naturally coming to an end. My TV show was ending, and a cycle of comedies I had been doing felt like they were coming to an end. And my 20s had just come to an end. It just felt like a big blank canvas ahead of me. He has that line “I’m 34 years, alone with a piece of paper.” When I read that line before I had agreed to do the movie, I was like: That’s it. It’s what’s genius about David Foster Wallace. He has the emotional capacity to express things where the best I could do is “I feel weird.” [Laughter.]

It’s really true. That’s what resonates with people about “Infinite Jest.” He could say these things about suicide and depression that express “just leave me alone,” which is what you and I may be capable of saying. You want to give it to people to read to say, “That’s how I feel. That’s what I’ve been trying to tell you.’ Anyway, I felt this moment in life. I needed to figure out something sustainable to make the next 50 years worthwhile, because this model of my 20s isn’t going to work for me anymore. I don’t want to be on this hamster wheel. For nine years I was on a TV show. I was writing a movie during the year, filming the TV show, then shooting that movie over the summer. It’s a lot.

In your 20s you are so driven by ambition and you really want to make sure it doesn’t go away. It felt OK, until it didn’t. At some point it was like, I can’t do this forever. I don’t feel good. I’m tired. The work is suffering. I’m not feeling inspired. There were moments when I would think of an idea and be like [miming exhaustion and deflation], “Oh, that’s a good idea.” That’s a bummer of a way to feel as an artist, when you aren’t inspired to do the actual thing you are good at. When I read the script and read this moment, I just really related to it.

To answer your question, I think what I zeroed in on, from a lot of what he said, was being careful where I place my value and taking the focus off results. When they said “That’s a wrap on Jason Segel,” for “The End of the Tour” -- it’s the first time this has ever happened to me, but I had this moment where I felt like, well, I’ve done the best I can. Now I might see this footage and find out that everything we shot was out of focus. As you get older you realize shit happens. I’m responsible for doing my best, and at that point I need to let myself off the hook. A big part of it is making friends with yourself. He has this great quote that I often have to paraphrase because I don’t remember it exactly. It was on one of the tapes. He said, basically, that you have this other you that you live with your whole life. It’s the voice at night that tells you you are OK or tells you you are nothing. I better make friends with that voice.

That meant so much to me. I think anybody in this room would be lying if they said they didn’t know what he was talking about. We all know the voice. That voice is like your fucking crazy friend. You learn to manage your crazy friend. He hasn’t slept. Let’s make sure he gets a nap. He’s hungry. These are dumb things, but you learn that they are true. It falls into the category of taking care of yourself, being good to yourself. So learning to let myself off the hook has been a really big one.

Let’s get back to another issue you mentioned earlier, Wallace’s idea that the things that are supposed to bring us happiness and pleasure, the things our culture has been founded on, are maybe not working the way they’re supposed to. Two things about that: One, that’s potentially a dangerous thing for a guy in your position who has made a successful career in movies and television to start thinking about. And two, that was the source of some of the distress among Wallace’s fans when you were cast. There was a disconnect, in their view, between this guy who has mostly done mainstream comedy, and a great American novelist.

I would say a couple of things. One of the things that Wallace talks a lot about is dosage. I think he’s absolutely right. The difference between having a glass of wine with dinner and getting wasted. Those are different things and people can handle them differently. There’s value to entertainment. I don’t think David Foster Wallace would ever argue that point.

Yeah. Well, he didn’t have a TV in the house because he felt he would end up watching it all the time.

Absolutely. And he loved movies. He could talk about them at length. He did on Charlie Rose. I think that having hypothetical anxiety about something that you haven’t seen yet and then devoting the time to comment on it on the Internet is probably reflective of someone who hasn’t fully assimilated the ideas that David Foster Wallace was trying to espouse. I think that that’s fair. I don’t know if there’s some version of that that’s inflammatory. I hope there is not.

I will do my best to make it sound that way. [Laughter.]

I know. But I really think to focus on something that’s actually happening is a really big part of the message. You have better uses of your time than to be devoting negative energy to something that hasn’t happened yet.

How do you, as someone who has been in show business a long time, young as you are, see the balance in our culture? In terms of entertainment and art, or whatever terms we want to use, are we eating a balanced diet? Or are we basically binging on carbs and getting wasted every night?

Can I go back a second? I thought of something that informs what I mean. I’m really guilty of it too, but I had a realization a while ago about pre-worry. I set up in my mind this thing that’s going to be a disaster in a week. I spend that week thinking about it and worrying about it, and then the thing happens and it is totally different from how I pictured it. That doesn’t mean it went great. It could have gone horrible also. But it sure went different from how I pictured it. Every time, your skills of predictability are always lacking. What a waste of time it was, between finishing shooting the movie and the movie coming out, to be so scared if people would accept me as David Foster Wallace. That is time that I could have been using in a much more rich way. That is how I feel about the negative comments on the Internet. Use the time for something better. Use this as your proof of concept. It worked out just fine.

Anyway, yeah -- our relationship to consumption. I think you have to just be really careful about consuming. I think there needs to be some responsibility on the providers. When I see that clickable link, “10 celebrities and their fat spouses,” I feel bad for the celebrity and their spouse, but I feel really bad for the consumer. There is a message being given to them that this is fun. Then you click on it, and you do have some strange satisfaction for a moment, and it changes you. In very small ways. Then people go around wondering why my kids are bullying each other and refuse to look in the mirror and make the connection. It’s because we are all acting this way and deciding it’s OK. It’s eating three cheeseburgers and chili fries and then at night being confused why your stomach hurts.

It’s the same thing when you wonder why you don’t feel good about the cultural stuff. Well, it’s because you are consuming trash. It’s actually not designed to make you feel good. It’s designed to addict you. It’s designed to keep you clicking on those links – that one leads to another fun list, like “10 major talk-show fails.” It’s really hard, because I understand why it’s interesting. I really do. If I engage in it I’ll do those clicks too.

I could suggest that the Hollywood production system, where you have worked, operates on the same principles. If the studio is sinking $100 million into a movie, they want it to push those same buttons.

Oh, sure. If you are capable of taking in a little of that stimulus, of looking at one of those lists and then walking away unchanged, then good for you. That’s not my experience with it. I have a million fucking browser windows open by the end of that thing. I just feel gross.

“The End of the Tour” opens this week at the AMC Loews Lincoln Square and the Angelika Film Center in New York, and the ArcLight Hollywood and the Landmark in Los Angeles, with national release to follow.

By Andrew O'Hehir

Andrew O'Hehir is executive editor of Salon.

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