How Playing David Foster Wallace Changed Jason Segel's Career and Life

Jason Segel — the amiable (and reliably goofy) star of such comedy hits as Forgetting Sarah Marshall and The Muppets, as well as the long-running TV series How I Met Your Mother — doesn’t wear a mask, shows no signs of Gyllenhaal-esque physical punishment, and never even puts on a silly accent in his new film, The End of the Tour. But it’s impossible to understate the changes he underwent to play the late author David Foster Wallace.

In the most challenging role of his career, Segel goes all-in for his portrayal of Wallace, the author and social observer who wrote several critically acclaimed books before committing suicide in 2008. Segel not only attempts to replicate Wallace’s idiosyncratic appearance (long hair, bandanas, an ever-present cigarette), but also the writer’s thoughtful, paragraph-length, and seemingly off-the-cuff soliloquies about life, art, and humanity.

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There was no shortage of cynicism or criticism when it was announced that Segel would play the author in the movie, which is adapted from David Lipsky’s 2010 book Although Of Course You End Up Becoming Yourself, about a road trip he took with the author in the mid-’90s. But for Segel, it felt like a role he was absolutely meant to play.

The film co-stars Jesse Eisenberg as Lipsky, who interviewed Wallace for a Rolling Stone profile during the last five days of Wallace’s Infinite Jest book tour. The story never got published, but the transcripts were turned into a book soon after Wallace died. Five years later, their conversations became the basis for the film, which won raves when it premiered at Sundance. The role has given Segel early Oscar momentum — a strange position to be in given Wallace’s disdain of professional praise. Segel spoke about the life-changing experience in a conversation with Yahoo Movies on Tuesday.

When you made this movie, you were 34 years old, and you’d experienced a lot of success — but you didn’t know what was next. And that’s exactly how David Foster Wallace is feeling when we first meet him in The End of the Tour. So you must have seen something of yourself in him.
I think that the thing that I really identified most … how old are you?

I’m 29.
I think it happens around 30, maybe a little later, but you labor in your twenties under this idea that, “if I just achieve this stuff, then I’m going to feel good.” I had a twenties of achieving a lot of stuff. And then I found myself at the end of this run of comedies, and my television show came to an end, and just feeling like, “What now?” When you’re young enough and [success] happens, looking forward 50 years is a pretty intimidating thing. That is a big, blank canvas. I think that’s what I really identified with. I had achieved quite a bit, and then I was still looking at this huge empty canvas. From a press tour perspective, I was fully aware that on the Infinite Jest press tour, after [Wallace] unloaded a 1,000-page book and it’s called “The book of a generation,” somebody on that tour — if not everybody — [asked him], “So what’s next?”

In the book, he talks about his fear of being addicted to TV, and how he doesn’t have a TV, because it was too easy to get sucked in. He compares sitcoms to candy. So, as someone who did a sitcom for nine seasons, did doing this movie make you think more about the work you’ve done, and will do?
I think there’s value in all sorts of different types of entertainment. It’s one of the things that I’ve learned as I’ve gotten older. I felt a real pull because on one hand, I was doing a sitcom, and on the other, I was making movies with this group of people who were really pushing the boundaries of comedy. And there were two very antithetical versions. And I learned as I’ve gotten older that there’s value to all of that. The thing I’d like to do now is to be really deliberate about how I use that time and energy. To make one or two movies a year that you would like to have a conversation about when you leave the theater would be a really great thing.

He also feared television because the makers of it have no responsibility to the people who consume it.
He talks a lot about dosage, and I think that’s a really important thing. Thinking that entertainment is going to satisfy you is probably a bad decision. But a movie like this — I think that it’s a very particular dosage. You go and you watch it for an hour and a half, and it’s meant to inspire a connection when you leave the theater, because you are hopefully going to have a conversation with the people you saw it with.

Were there any words from the interview or the script that stayed with you, made a difference in your life?
Well the one that just really resonated with me was when he said, “When this is over, I’ll have to face the reality that I’m 34 years old, alone in a room with a piece of paper.”

Part of his mantra at this point in his life is that he’s trying desperately to structure his life to avoid bouts of depression and maximize his writing talent, which is something that struck me.
He also talks about how there’s this other you — the you at night who either tells you everything is fine, or that you’re nothing. And he says, “It’s only now in my thirties that I’m learning that I have to make friends with that other me.” And that’s a really important thing about getting older. That’s going to be a lifelong relationship, you and this other voice.

Is that a relationship you’ve begun to build?
If you listen to [Wallace’s 2005 speech] “This is Water,” you feel like he’s been working through those ideas a little bit, and zeroed in on [the fact] that it’s maybe placing your value in community and being a good friend and family member and being at one with what is going on around you. And I think there’s a lot of truth in that: Be kind to people, take care of yourself, and pursue your passion as hard as you can, and then you’ve got to let yourself off the hook after that. Those are the things you have control over.

The book and movie are profound on their own merits, but Wallace also killed himself 12 years later, and that hangs over the whole experience as a viewer. But as someone who had to play him in that moment, did that impact you at all?
What I tried to do is just try to play those four days as purely and accurately as possible, which meant that he only knew what had happened up until that point in his life. But that was a question, I thought a lot about: Do you put in foreshadowing? And what I thought was, if you play those four days accurately, the foreshadowing is built in. I don’t know what’s going to happen to me in 10 years, so for me, to be somehow indicating that would be false.

Wallace wasn’t immune to wanting praise, but he was afraid of it becoming his focus. And now you’re going to go release this movie and be talked about for an Oscar nomination, and go through that process, for playing him. Do you have the same sort of fear of that praise?
No, I think I’ve constructed a good system for myself where I try to work as hard as I can and focus on what is actually going on around me. I’m thrilled that people like the movie, and my biggest hope would be that people read more David Foster Wallace as a result of the movie. Beyond that, I try to do those same things that we talked about.

I saw the movie, and then read the book, so I was hearing your voice as I was reading it. He wasn’t a TV or movie star. So in a strange way, you are intrinsically tied to his legacy; for many people, you are him.
I think honestly, if seeing the movie makes people think, “Maybe I should pick up some Wallace and see what they’re talking about,” that would be an amazing thing, because reading David Foster Wallace really impacted the way I think.

In what way?
One, the question of where we place our value became incredibly important to me. And then two, just really zeroing in on realizing that, while every indication is that you’re the center of your own universe, everyone around you feels the exact same way, so maybe we should realize that we’re all in this together. [It’s about acknowledging] that there’s no real center, and everyone out here is just guessing.

So you have this profound experience shooting an intimate movie, playing a guy who is a complicated genius; how did you come down from this? What did you do after it wrapped?
Well, I live on an orchard, and I just went home and I did nothing for quite a while. I’ve learned to not view time in which I’m not working as waiting. I’ve made friends with the fact that that’s life. This is life, also. And at some point, you might even want to retire: What then? If you haven’t made friends with time-off at that point, it’s going to be a tough lesson. I’ve just really been enjoying life stuff. I hike, I have a really pretty vegetable garden and so I cook from that — I’m learning how to cook. I go see movies sometimes.

Knowing that you’d sort of be Wallace for many people, how much did you try to actually sound like him?
I had a really wonderful dialogue coach and we tried to zero in on sort of the music of his speech, because it’s a guy who had an ability to talk in fully constructed arguments — just off the cuff, with a thesis, supporting points, and a conclusion. And so there was a rhythm to that we really tried to capture.

Lipsky was cynical about Wallace trying to trick him by acting like a modest country boy and not a genius author.
David Lipsky went in with some real assumptions and a real agenda, and then he was confronted with someone who was just trying to have a conversation…. Lipsky comes off as a really complicated figure. He comes off as a kid who has a lot to learn.

He was jealous of Wallace’s place in the world. Does that happen for you, even with your success?
I used to be [jealous]. I’ve learned that you do not know somebody else’s interior life. So when you think, “I would like to be that person,” you don’t know what they feel like, and that’s a really dangerous bet. You don’t know what they feel like at night before they go to sleep. And so I think that the best chance that you stand is to get so that you’re good before you go to sleep, and then bet on yourself.