For a while there it seemed that the coming David Foster Wallace movie was truly ill starred. Not only had it drawn the wrath of Wallace’s estate and his widow, but the casting of Jason Segel in the lead role — surely a stunt, Wallace’s fans said — had also unleashed howl after incredulous howl.
Wallace, who shot to literary fame for the voluminous 1996 novel “Infinite Jest” and hanged himself in 2008, was known for writing hyper-intricate fiction and nonfiction once described in The Times as “prodigiously observant, exuberantly plotted, grammatically and etymologically challenging.”
Mr. Segel, a Judd Apatow protégé, built a career out of deploying his hangdog countenance and aw-shucks manner to maximum comic effect — in the television series “Freaks and Geeks” and “How I Met Your Mother,” and films like “Sex Tape” and “Forgetting Sarah Marshall,” which he wrote, starred in and graced with multiple shots of his family jewels.
But late in 2013, Mr. Segel was sent the script for “The End of the Tour,” an adaptation of the journalist David Lipsky’s book recounting five days spent with Wallace during the promotion of “Infinite Jest.” Paging through the screenplay, Mr. Segel felt a rush of recognition. He was about to turn 34, the age Wallace had been at the time, and had also achieved success but was struggling with the question of what exactly to do next. That it was such a U-turn from Mr. Segel’s regular fare made the part only more tantalizing: Mr. Segel had grown weary of rote rom-com roles and was ravenous for change.
“I knew I was going to try it, immediately,” Mr. Segel said in an interview in the lounge of Manhattan’s Bowery Hotel. “When you start repeating yourself, it gets boring for everybody.”
Mr. Segel is as affable and endearing a presence as his on-screen characters suggest. He is also 6-foot-4 and, not wanting to seem intimidating, adopted the softhearted goofball act years ago, shrinking down, he said, “both metaphorically and physically.” Wallace was also a big guy, but playing him would be, for Mr. Segel, at long last a stretch. “I was terrified, of course,” Mr. Segel said.
After learning that Mr. Segel landed the part, many fans of Wallace were terrified themselves. “Jason Segel as DFW … a young Monty Hall to play Kerouac?” asked one of the many hand-wringers online. The naysaying went nuclear after a photo emerged from the set last year. It showed an excruciatingly ill-at-ease Mr. Segel guised as Wallace circa the mid-’90s — in granny glasses and a bandanna — wearing an expression that seemed to say, “I shouldn’t be here at all.”
The reaction was swift, merciless and riven with schadenfreude. One dissenter tweeted that Mr. Segel was clearly playing Wallace “as some sort of stoned idiot savant.” “Worst headband since Burt Lancaster in ‘Apache’?” asked a film critic at the Canadian newspaper The Globe and Mail.
Then, late in January, the film had its premiere at Sundance. Mr. Segel’s performance — empathetic, nuanced, whip smart — left the packed theater breathless. And Twitter ended up eating crow.
“Yes, Jason Segel is great as David Foster Wallace,” announced Vanity Fair. “All concerns were for naught,” said IndieWire. “It’s early, but let’s prep Jason Segel’s Oscar campaign just to be safe,” said The Huffington Post, echoing what Vulture posited the day before.
It was the reaction James Ponsoldt, who directed the film (opening on July 31), said he had anticipated ever since production began. “We all felt we had this secret treasure,” he said.
A devoted David Foster Wallace fan himself — he had excerpts from Wallace’s memorable commencement speech at Kenyon College, “This Is Water,” read at his wedding — Mr. Ponsoldt said he knew within minutes of meeting Mr. Segel that he was the one. He found the actor deeply thoughtful, he said, markedly different from his television persona. “He’s a really complicated guy, who’s only begun to reveal his real potential as an actor,” Mr. Ponsoldt said. “It’s like with Tom Hanks, Robin Williams, Bill Murray, Jamie Foxx. A lot of our favorite actors were put in a box before they destroyed that box.”
One faction that Mr. Segel and the filmmakers are unlikely to ever win over, though, is the David Foster Wallace Literary Trust, Wallace’s widow, Karen Green, and his closest editors. In April 2014, the trust issued a withering objection to the film, saying Wallace would never, if alive, have agreed to it. That the trust could not stop the film — certain privacy rights do not extend to the dead or to their estates — only heightened their ire.
The film’s warm reviews have not swayed them an inch. Michael Pietsch, Wallace’s longtime editor, wrote in an email that Wallace’s writing made clear his anguish about being a public figure and “his overwhelming anxiety about being on the wrong side of the screen.” Alex Kohner, the co-trustee and lawyer for the trust, said that when Wallace agreed to be interviewed by Mr. Lipsky, he did not consent to be portrayed in a film. Mr. Kohner also said he contacted the producers as soon as they learned about the film, but that the “objections fell on deaf ears.”
“In my opinion it is unlikely that the filmmakers could have legally capitalized on the unpublished interview and David’s good name if he were alive,” Mr. Kohner wrote by email. “Regardless of whether or not this film has entertainment value we question the ethics of their actions.”
Via a spokeswoman, the producers said they had been under the impression that “Wallace’s camp” knew Mr. Lipsky’s book was to be made into a film and that the producers had not known of the opposition until shortly before production began, when it was too late to turn back. “We are very proud of the film, and as deep admirers of his work, were always committed to honoring the memory of David Foster Wallace,” three of the five producers, David Kanter, James Dahl and Matt DeRoss, said in a statement.
Mr. Lipsky did not respond to repeated interview requests and, at the last minute, said through a representative that he was on a deadline and had no time to speak. Mr. Ponsoldt would not address the trust’s grievances, but a person close to him said he had not been aware of them until late in the process and felt terribly about them. Donald Margulies, the Pulitzer Prize-winning playwright who wrote the screenplay, said the objections made everyone involved feel badly. “We’ve approached this with such, we think, humanity,” he said.
The film was neither a hagiography nor a biopic, Mr. Margulies said, but a story told from Mr. Lipsky’s point of view, about time spent with a fellow writer who had rocked the cultural firmament and been anointed a genius, a label Wallace both wrestled with and deserved. Mr. Margulies conceived of the film as a “really smart road movie,” with the protagonist being Mr. Lipsky (played by Jesse Eisenberg).
The film originated in an assignment that Mr. Lipsky did for Rolling Stone, spending nearly a week with Wallace during the final leg of his triumphant book tour. Mr. Lipsky, as admiring of Wallace as he was envious, recorded, on cassettes, their winding, heady conversations in Wallace’s home, in diners, in cars and on planes. The piece was canned, but after Wallace’s death, Mr. Lipsky used the material for an award-winning article that ran in Rolling Stone and was the basis for his 2010 book, “Although of Course You End Up Becoming Yourself.”
To prepare for the role, Mr. Segel listened to Mr. Lipsky’s recordings exhaustively, watched clip after clip of Wallace online, formed a small book club with friends to go over the 1,079-page “Infinite Jest” in 100-page chunks, and rented a cabin by himself in the California boonies to read undistracted. He had bought the book in a store, and after plopping it down on the counter, he recalled, the saleswoman rolled her eyes. “She said: ‘ “Infinite Jest.” Every guy I’ve ever dated has an unread copy on his bookshelf,’ ” Mr. Segel recalled. “That experience alone made it worth it.”
Anticipating the storm of sniping after he was cast, Mr. Segel said he also largely stayed offline, save for the occasional visit to a techie site. “I had to immediately eliminate any voices that were telling me that ‘You’re incapable, you’re the wrong guy,’ ” he said. “Which is fairly easy to do if you don’t use the Internet.”
He left to begin production the day “How I Met Your Mother” wrapped, a shadow of Wallace-esque stubble on his face, something he still feels lingering regret about after having been clean-shaven for each of the show’s nine seasons.
To play Wallace, he said he worked to strip away any vanity or hint of pretense or self-satisfaction, and strived, moment by moment, to be as honest and empathetic as he could be. “Infinite Jest,” he said, ended up being the biggest influence on how he played the role.
“It felt like an S.O.S., saying, ‘Does anyone else feel this way?’ ” Mr. Segel said, “That there’s something about the American promise that x, y and z are going to satisfy this itch that you’re not enough, that a whole generation found to be a false promise. No achievement or pleasure or entertainment or consuming is going to be the thing that makes you feel like everything’s O.K. And it really hit home with me. Because you really are still you when you go back home at night. No matter what award you’ve gotten or how much money is in your bank account, you feel the same going to sleep.”
That said, Mr. Segel admitted to feeling pretty good that his performance and the film have drawn such praise: He was able to show himself and most everyone that his departure from comedy has real legs. He also said he was still exploring what do next, though early reports have him in a drama with Rooney Mara. While playing the role helped scratch his own itch for deeper, darker roles, it still left him hungering, he said, for infinitely more.
Correction: July 26, 2015
An earlier version of a picture caption with this article misidentified the hometown of the writer David Foster Wallace. He was born in Ithaca, N.Y., and moved with his family six months later to Champaign, Ill.; his hometown was not Bloomington, Ill., where he is depicted in the photograph, taken in 1996.
Correction: July 27, 2015
An earlier version of this article misstated the number of pages in “Infinite Jest.” It is 1,079, not 1,029.