The End of the Tour: David Foster Wallace deals with being David Foster Wallace.

Longer intro: In which a curly-haired journalist (me) interviews a famous person (writer/director/actor Jason Segel) about, among other things, the experience of being famous during the famous person’s publicity tour for his movie (The End of the Tour) about a curly-haired journalist (David Lipsky) who interviews a famous person (author David Foster Wallace) about, among other things, the experience of being famous during the famous person’s publicity tour for his novel (Infinite Jest).

Shorter intro: The End of the Tour is a film based on David Lipsky’s nonfiction book Although of Course You End Up Becoming Yourself: A Road Trip with David Foster Wallace, starring Jesse Eisenberg and Jason Segel. I was fortunate enough to speak with Segel when he visited San Diego.

Matthew Lickona: You’re portraying a man who is intensely interested in curating how he’s perceived. He’s worried about how Lipsky will portray him in the article, about whether his bandana will come off as an affectation. What would you say to David Foster Wallace about your portrayal of him: what you saw in him and how you tried to get it across?

Jason Segel: I think I would say the same thing I would say to anybody who was worried about perception — because I deal with it constantly — that the reality is, everything is okay. It’s really hard to wrap your head around; it’s like they say, “It’s simple, but not easy.” But the reality is, everything is okay. I think there’s a recording from the trip where he says, “I’m using all the mental gymnastics at my disposal” to feel a certain way. And I think that when you’re dealing with the sort of issues that David Foster Wallace was dealing with — the same issues that, maybe to a lesser extent, we all deal with as human beings — that’s [what’s required for] wrapping your head around the truth that everything is okay when it comes to those issues.

ML: So then, as far as what you saw and how you sought to portray it?

JS: All I could do was try to approach the part with great empathy and love, and try to focus on the themes of Infinite Jest and This Is Water [Wallace’s graduation speech to the Kenyon College class of 2005]. Because when you do a press tour, which I’ve done for movies, you are talking and thinking about the themes of the movie for that entire month. And this movie takes place at the end of the Infinite Jest book tour, so those themes are the things that he’s thinking and talking about daily. At least, that’s my experience with a tour. And I felt like he was trying to communicate something very particular and very important: the idea that “I’ve been told, culturally, that if I do certain things, I’m supposed to feel okay, and I don’t feel okay. Does anybody want to join this conversation with me?”

That was something I really related to. I think that men — especially of our age — arrive at a moment where we realize, “I’ve been working really hard in my 20s to get there, and I’m starting to think there might not be a there.” I think the whole movie is an extension of something that David Foster Wallace wrote really hard about. Infinite Jest is three-pronged: there’s addiction recovery, a tennis academy, and an international conspiracy involving entertainment. They represent, as I understand it, pleasure, achievement, and entertainment. And in all three, there is someone who is feeling empty.

ML: Were there other ways — besides reading the book — that you found your way into the character?

JS: I think it was a line from the script where David Foster Wallace says, “Now I have to face the reality that I’m back to being 34 years old, alone in a room with a piece of paper.” As a writer myself and an actor, I know that is a reality you face at the end of every job. And I was sort of dealing with that on a massive scale, because I had been doing a TV show for almost a decade, and it was coming to an end right as we started shooting this movie. I was very much left with the feeling of “What now?” in combination with, “What is going to sustain me if I’m going to do this for another 50 years?” I had stopped feeling hungry, like I needed to do stuff, the way I needed to write Forgetting Sarah Marshall. And I had stopped feeling scared. And for someone who likes to find out his limits, those are two really necessary things. I needed to find something that did that, and this film certainly did. I was terrified.

ML: Someone might say, “If you’re not hungry and scared any more, can’t you just stop and be happy? Why look for hunger and fear?”

JS: The interesting thing is reaching the conclusion at 30. If you reach it at 65, that’s probably a good time to say, “Great, I’m off to Hawaii.” But one of the themes Wallace is writing about is, “When you reach that moment at 34, 35, something is off. You need to reposition where you’re placing your value.” I think there’s a sense of connection and community that fills a hole that I don’t think achievement fills. I hope the conversation that’s raised among people after seeing the movie is that maybe connection has been underprioritized in their lives.

ML: A good bit of the dialogue is taken directly from Lipsky’s tapes of his conversation with Wallace. You told Entertainment Weekly, “This isn’t quippy dialogue; these are well structured theses on every comment he’s making. So you really had to understand what you were saying.” Given that, is there anything that really sank in and stayed with you?

JS: I believe this was on one of the tapes that Lipsky gave me to listen to: David Foster Wallace refers to this “other you.” Everybody has an “other you” that you’re saddled with for your whole life. It’s the voice that either tells you that you’re a piece of shit or that you’re doing great and everything is going to be fine. And one of the really important things he’s realized is that he needs to make friends with that other you. I thought that was really profound. Because we all know that voice.