Knowing Yourself All Too Well: A Conversation about ‘The End of the Tour’

Infinite JestThe End of the Tour, the recently released drama directed by James Ponsoldt and starring Jason Segel and Jesse Eisenberg, is based on interviews with the late author David Foster Wallace, conducted by Rolling Stone journalist David Lipsky, who joined Wallace during the last five days of the Infinite Jest book tour in 1996. Segel, an actor generally known for his comedic roles in movies such as Forgetting Sarah Marshall and The Muppets, portrays Wallace, opposite Eisenberg (The Social Network, ) who plays Lipsky. The film itself draws from Lipsky’s 2010 memoir, Although of Course You End Up Becoming Yourself: A Road Trip with David Foster Wallace.

The film has already managed to generate some level of controversy, mostly from fans of Wallace’s work (and his literary estate, according to Wikipedia), who argue that the writer would be opposed to the idea of an actor portraying him onscreen. ZYZZYVA asked its blog contributors Zack Ravas and Henri Lipton to attend an advanced screening of the film. Both Ravas and Lipton went into this film with different perspectives, in the sense that Ravas was familiar with David Foster Wallace but had not yet tackled the tome that is Infinite Jest, whereas Lipton was already well versed in Wallace’s published works. The following is a conversation between them about the movie.

Although of course Zack Ravas: As a fan of Wallace, Henri, how did you end up feeling about the way The End of the Tour depicted him?

Henri Lipton: First of all, Jason Segel did an admirable job. I suppose one could view this particular casting as a disservice to the monstrous intellect and complexity of Wallace and his writing-–it seems like many did. But casting a biopic is always a fraught thing. Particularly because Wallace’s appearance in some ways belied his intellectual gifts, this must have been even more difficult than usual. It’s easy to pick among a stable of old white men with wispy hair to play Leo Tolstoy, but not many people who look like David Foster Wallace can get their mouths around his verbiage, let alone act.

ZR: When I think about Jason Segel as an actor, I generally associate him as a comedic actor thanks to his roles on TV’s How I Met Your Mother, not to mention his affiliation with his former Freaks & Geeks cast members in films like This is the End. I for one was impressed that Segel was successfully able to play down his traditionally goofy persona for what might be called a breakout role here in The End of the Tour. When I expressed this sentiment to my roommate and his girlfriend, who’ve read Wallace’s work, my roommate quipped, “So you mean he actually acts in this one.”

Nothing against Segel personally, but like many of the fellows of the actors in his circle (Seth Rogen comes to mind), he’s known more for playing himself onscreen or, at the least, playing to a type. Here, he’s very low-key and unassuming, to the point that I wasn’t even thinking about Segel the actor, but David Foster Wallace the writer. I was equally impressed that the movie doesn’t go for any show-y, traditionally dramatic moments—no crying scenes or explosive arguments—and yet I walked away feeling like I’d witnessed a great performance.

HL: In mannerism and cadence, I thought it clear that Segel had done his homework. But I must confess that I think the whole enterprise of casting actors as writers is overall a doomed one, as it will always stir up feelings of resentment among critics of actors and lovers of writers alike, each camp grumbling about the audacity of the filmmakers and the actors in their efforts to “bring to life” someone we understood primarily, if not exclusively, through words on a page.

ZR: As for a critique, I at times questioned if the filmmakers went “too far” in emphasizing David Foster Wallace’s “regular guy-ness” as Lipsky puts it, with plenty of scenes of him lamenting his status as a horny single guy. But I have to wonder if I’m simply falling into the trap of wanting to idolize great writers as being somehow more elevated and virtuous than the rest of us. Perhaps the movie is actually a more realistic subversion of this very same trope—typically, nothing is less interesting than a biopic where the main subject is portrayed as a flawless saint.

HR: I definitely appreciated how the movie clearly went to great lengths to depict both characters as petty, flawed, and childish despite their obvious intelligence and achievements. Part of this has to do with the material they were working with, as the hostility and resentment percolating throughout these conversations were necessarily going to bring out the worst in each of these writers. Two smart guys with similar vocations, at different stages in their careers, each caring very deeply about how the other sees him, for different reasons, are going to butt heads.

I do think the film emphasized David Foster Wallace’s “regular guy-ness” as well as his tendency to emphasize it in himself. I appreciated the inclusion of Lipsky’s direct challenge to Wallace about this, when he called him “faux,” a characterization that Wallace spent many years of his life describing as among his worst fears. I thought many of the ways they worked in Wallace’s indulgences, in junk food and television, were interesting and funny and ultimately poignant, but I thought the elements of Wallace’s protectiveness of his ex-girlfriend were mishandled, or at least a little bit ham-fisted. I didn’t need lingering shots of Wallace glaring at Lipsky from the next room over as Lipsky flirted for the umpteenth time with Wallace’s ex-girlfriend.

ZR: This was without a doubt the least effective component of the film for me as well. The scenario that plays out between the two men over Wallace’s ex-girlfriend was the only time I had the impression that the screenplay was trumping up drama for the sake of drama, rather than letting it naturally emerge from the interactions between characters. It felt, in a word, artificial.

HL: The film definitely used that as a catalyst for some of the most interesting and baldly confrontational moments toward the end, but I can’t help thinking that Wallace’s exhaustion after touring—compounded by his discomfort with the interviewing process—and Lipsky’s frustrations with his career and the interview itself, were what really sparked the intense and conversationally fruitful acrimony.

ZR: I want to play devil’s advocate a bit and ask: do you think there was any possible way the filmmakers could have attempted to incorporate a bit of David Foster Wallace’s writing style into the visuals (whether by editing, onscreen graphics, etc.) of the movie? Granted, I’m sure some fans of Wallace would have rolled their eyes if footnotes had appeared at the bottom of the screen during key moments. Though the movie is consistently engaging because the conversations in it are intellectual, literary-minded, and touch on a host of fascinating subjects, director James Ponsoldt doesn’t choose to push the film anywhere visually interesting.

HL: I would have been one of those fans. I am grateful to the filmmakers for their restraint, and think the film would have been disastrous had they tried to stylize it in some obvious way. It’s not an adaptation of Wallace’s work; to my mind it’s an examination of success and ambition and peers and respectful animosity, and it uses some fantastic quotes from smart people, one of whom is the most neurotically uncomfortable successful person I’ve ever heard or read. We don’t learn that much about the book, really, and that’s fine, because the dialogue focuses on the writers’ reactions to its publication, its success, and its cherishment, which Wallace obviously wanted but struggled with, and which Lipsky obviously envied but respected. When they make a forty-hour-long Infinite Jest adaptation they can get cute with footnotes, but I really thought the film’s muted feel gave it grace, and, perhaps most important, gave the actors room to read each other and to inhabit their often cramped, always tense spaces.

ZR: One of director James Ponsoldt’s earlier films, the 2012 indie drama Smashed, follows a young married couple grappling with alcoholism. Arguably his most satisfying film, The Spectacular Now (2013), concerns a high school senior who relies on alcohol as a means to keep from thinking about a host of issues in his life, including an absent father. Certainly, the specter of addiction hangs over The End of the Tour, as David Foster Wallace freely admits to being addicted to television in his youth and David Lipsky’s editor pushes him to question Wallace regarding rumors of his past heroin use. I read an article from the Chicago Cinema Circuit that posits these three most recent films from Ponsoldt serve as the director’s “Addiction Trilogy.” This film, however, is less interested in depicting addictive behaviors than utilizing them as context, a springboard for conversation between the two characters.

HL: Infinite Jest posits addiction, whether to drugs or entertainment or self-harm, as a way of escaping the claustrophobia of the self. Television, as a distraction, allows a hyperactive mind a respite from the sort of existential pain that plagues so many of the characters in the novel, and that by all indications Wallace suffered throughout his life. He wrote a story in college that describes depression as a kind of subatomic sickness, wherein every molecule in the brain and body are sick and nauseous. Drugs do the same thing as television, in a way, and the allure of changing one’s state of mind is obviously rooted in the desire to escape from oneself.

Much of what the book does is to show how addiction to something is more than an obsession with a particular feeling or activity; it is the phenomenon of finding something that allows a break from overwhelming feelings of psychic sickness, to badly plagiarize Wallace, and sticking to it. What that something is is not irrelevant, and of course can be explored psychologically and philosophically and can say a lot about a person. Ultimately, the addiction matters less than the reasons for allowing oneself to fall into an addiction.

ZR: About midway through the film, the two men have a frank discussion in the Mall of America in which Wallace laments how it’s almost easier to create art from a place of obscurity, scoffing at the masses who are too ignorant to grasp your work. Because as soon as you achieve commercial success, a part of you starts to wonder,  “Gee, all those people who I thought only spent money on stupid, insipid entertainment are now spending money on my book. What does that say about my book?!” For me, these kinds of artistic conversations—supposedly about 70 percent accurate to the recorded interviews between Lipsky and Wallace—were the most compelling part of the film.

HL: Absolutely. It’s always fascinating to see how Wallace as interviewee is so similar to Wallace as writer. Both are so obsessed with getting “there” first. What I mean by that is that Wallace clearly catalogued everything bad that he had ever thought about himself, and anything bad anyone had ever said to/about him, and anything bad he could imagine being said about him, and went to lengths to prove that he had considered every permutation of his failures as a writer, or even as subject of a profile. (He did study modal logic in college, after all). Even in Infinite Jest, at times the narrator is so compulsively concerned with proving that he knows something might be corny, or cliché, or sentimental, that it can feel ingratiating, even as some of the explosive technical writing is distancing and feels like the exact opposite. In this way, Wallace as thinker and prose stylist (and, I imagine, philosopher) sets up these closed systems in which he tries to circumvent criticism or anticipate it by levying it against himself before anyone else can. It’s exhausting.

ZR: In the end, as long as they’re able to get over the fact that a movie about David Foster Wallace exists, I think The End of the Tour will prove of great interest to writers, in the sense that it features some excellent discussion on the nature of literary success and artistic “genius.” In the film, David Lipsky’s jealousy toward Wallace is palpable.

HL: I imagine that had I not been familiar with Wallace’s writing, and had I not actually read and/or heard him say much of what is used as dialogue in the film, I would have been more interested in Lipsky’s character. Wallace sort of hovers above throughout much of the film, and Eisenberg’s performance should not be discounted for its honesty and complexity, in bringing to life a character whose relationship to his own ambition the vast majority of theatergoers will be better able to understand than Wallace’s.

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