Lipsky told me at Sundance that he was relieved at the time that he didn’t have to write the feature, as other things came up and pushed it aside. Segel says the movie is like the trajectory of a relationship as they first meet, start to know each other, get comfortable, then intimate, then angry, and break up. They never met again. Wallace was in relatively good shape in 1996; he fought depression without finding effective medications until he took his own life in 2008.
The reason there is a movie about David Foster Wallace, even though it went against the wishes of the DFW Literary Trust and family (including Wallace’s wife Karen Green), who protested the film as it was under way, is that the Trust had no control over Lipsky’s 375-page 2010 book based on the taped 1996 conversations Lipsky had with Wallace, “Although of Course You End Up Becoming Yourself: A Road Trip with David Foster Wallace.” At the time, the Trust did support Lipsky’s book. And Rolling Stone, which went along with Lipsky’s reluctance to write up the trip back in 1996, did have the sense to finally publish Lipsky’s interviews in October 2008 after Wallace’s death. Lipsky owned the rights to those interviews, which he faithfully transcribes verbatim in the book. “It’s the one way of writing about him I don’t think David would have hated,” he explains in the introduction. The estate had no rights to this material. And no legal recourse to stop Ponsoldt’s film.
A few months after Wallace’s death, in fact, his sister Amy wrote to Lipsky:
“My own anxieties are many. My brother was a hilarious guy, a quirky, generous spirit, who happened to be a genius and suffer from depression. There was a lot of happiness in his life. He loved to be silly, he made exquisite fun of himself and others. Part of me still expects to wake up from this, but everywhere I turn is proof that he’s really most sincerely dead. Will he be remembered as a real, living person?”
To that end, both the book and the movie serve the function of promoting the author (in a positive way) and keeping him alive for many potential new readers. Production company Anonymous Content turned to Pulitzer-Prize-winning playwright and screenwriter Donald Margulies (“Dinner with Friends”), a professor of English and Theater Studies at Yale, to dramatize for the screen the rambling five-day book conversation, which reads much like a philosophical “My Dinner with Andre” on steroids.
That would not have worked as a movie. So Margulies fashioned a two-character drama, beefing up Lipsky (Jesse Eisenberg), an anxious, rivalrous, eager-to-please 30-year-old novelist/journalist interlocutor who falls for his 34-year-old subject, knowing he will never achieve his greatness — or his acclaim. Ponsoldt calls it “an unrequited platonic love story” in the vein of “Amadeus” or “Master and Commander.”
“Lipsky is aspiring to that which Wallace has just received, and the ambivalence and the doubt and the ambition and the jealousy and the need for approval, the need for recognition,” Margulies told me. “Validation by someone you admire is a very universal thing. I don’t think it’s just about artists; it’s in any field.”
It’s also that hollow feeling when you finally become famous. “It’s about the conundrum of artistic success,” said Margulies. “To want a success, to want an audience, but also want to work without distraction and the pressure of delivering to an audience repeatedly after that. And always feeling you are competing with yourself and your past accomplishments.”
And so Wallace is deeply uncomfortable with becoming illustrious. “Very few people are as talented as Wallace,” Margulies said. He preferred not to listen to Lipsky’s tapes (as the actors later did). “I didn’t want to be influenced by the rhythms of their speech. I needed to make my own world with it. It’s one thing to read the words on the page, but I didn’t want to hear it.”
Margulies frames the movie with Wallace’s suicide. “Because Wallace had died, I was motivated to read Lipsky’s book,” he said. “I was curious. I didn’t know a lot about Wallace. I hadn’t read ‘Infinite Jest.’ Reading the book gave me an introduction to Wallace.” Knowing that we lose him is very moving. “I think if we were to remove the bookends, and it was simply a guy going on a trip, it would have none of gravitas,” said Margulies. “What a chronicler of his time he was! And how we are deprived of his future output!”
Interviewing Lipsky gave Margulies a legitimate third act that is not in the book — the two writers’ big spat on the tour, when Wallace accuses Lipsky of flirting with his former girlfriend (Mickey Sumner). “I needed conflict, and there was none,” Margulies admitted. “I tried to capture just a little bit of what it was like to be young and 30 and a struggling writer in New York in 1996 — the hissing of egos.”
When he finished the script, Margulies persuaded his producers to send it to his former student Ponsoldt; they had stayed in touch over the years. “He always impressed me as a deep, funny sort of polymath, a voracious guy,” Margulies said. “He was between Sundances, between ‘Smashed’ and “Spectacular Now.'”
Angeleno director-on-the-rise Ponsoldt was raised by intellectuals in Athens, Georgia; his father was a Constitutional Law professor at the University of Georgia, and his mother wrote short stories. Ponsoldt was eager to direct this movie. First, he was a bonafide Wallace obsessive, from the time he was in high school covering the local music scene for an Athens alt-weekly. Arriving at Yale in 1997, it took him four to five months to get through “Infinite Jest,” a book everyone “was reading or pretending to read,” he said. “It was a book you had to contend with. It was a really emotionally brutal experience.” He read everything of Wallace’s he could find, and devoured Lipsky’s book when it hit bookstores.
Another lure was that Ponsoldt carries a real emotional nostalgia for Middle America: he once rode a bicycle from New Haven to San Francisco for Habitat for Humanity (it took two months and two days). Faced with a road movie talk-fest that breaks the rules of what the establishment considers safe filmmaking, Ponsoldt relied on his own gut: “It’s good to know the rules and get rid of them. Pleasure is pleasure, you know what you like. In this case, I really liked Lipsky’s book. I loved the quality of Wallace’s voice at that time.”
Rather than worrying about being judged, Ponsoldt decided to put his nose down and do the work, “knowing we’re making this for the right reason — love, respect, and admiration. People have been inspired to make plays or movies or novels about real people as long as those forms have existed.”
The movie touchstones for Ponsoldt were Wim Wenders’ 70s output, Robert Altman’s “California Split,” Brit classic “Withnail & I,” D.A. Pennebaker’s “Don’t Look Back” and Michael Winterbottom’s “The Trip,” which embodies all that Ponsoldt admires: “It’s a real curiosity in people and a democratic perspective on story, having an aesthetic sense that serves the story you’re telling.”
To find his stars, Ponsoldt did a thorough search and picked the two best brainy actors he could find: “I want to surround myself with people who are more talented and smarter than me, and who will make me better for it.” He and casting director Avy Kaufman (“Lincoln”) brainstormed and finally cast Segel, who wrote “Forgetting Sarah Marshall,” “The Muppets,” and an upcoming “Lego Movie” sequel, and New Yorker contributor and off-Broadway playwright Eisenberg. “They are great writers,” said Ponsoldt. “We didn’t want to do impressions. It’s wasn’t ‘Saturday Night Live.'”
Before the film world premiered at Sundance, indie distributor A24 scooped up “The End of the Tour.” In the movie Segel gives a brilliant awards-worthy performance as Wallace, unlike any other he has given before, because, Ponsoldt said, “he hadn’t built a role on real research, real understanding.”
He and Eisenberg showed up on set very prepared, Segel told me in our Flipcam interview. He’s aware that he’s hardly typecast in this role. He and his costar enjoyed the level of tennis they were playing, which helped to up their game.
Segel organized a “book club with three great book dorks” to read “Infinite Jest” together, but while he digs the author, it’s not necessary to know Wallace’s work to understand what the movie is about.
While one critic who knew Wallace well complains about Segel’s portrayal of Wallace as lacking verisimilitude, two of the author’s close friends defend it. Illinois State University’s Charles Harris hired Wallace to join the English Department faculty, where he taught for ten years through the publication of “Infinite Jest.” Charles and his wife Victoria Harris showed Ponsoldt around the Bloomington-Normal area (the film shot in Michigan for tax breaks); they visited his office and house and some of the places Wallace took Lipsky to eat.
“I think David would have appreciated the movie,” said Charles Harris on the phone. “James Ponsoldt and the actors, particularly Jason Segel, did it with a great amount of care and integrity; they did not try to exploit David. They tried to get him as he was, the best they could. Most importantly, Jason Segel got it right, which I thought was remarkable, he was not the person who immediately comes to mind, but he really nailed it. He didn’t try to imitate David, he tried to get him from the inside.”
The Harrises saw the movie at the David Foster Wallace Conference, where they say it played well to the DFW Howling Fantods. “I went to the movie with dread,” admitted Victoria Harris, who was on the ISU search committee. “It could have been really sickening, but I felt I was with David again. Jason captured David and his movements and some of his flinches, so well, with the dogs, with dead fish in his pockets.”
Ponsoldt also met in L.A. with the Harrises’ daughter Kymberly, who dated Wallace for a time. “Kymberly was really moved,” said Victoria Harris. Did Victoria know that her colleague Wallace was depressed? “I may not have sensed it but I knew it,” she said. “There’s an [Austrian] author he loved, Thomas Bernhard. I had to read them all. Every novel had a death by hanging in it.”