“A beautiful thought is a beautiful thought, no matter what the sign above the shelf where you encounter it.”

Photograph of David Lipsky by Shaun McDowell

An Interview with David Lipsky

David and David. Two strangers with a lot in common took a five-day road trip in 1996, a trip that wound up becoming as public as it was private, that travelled as far into being a writer as into being a person. “I want to be able to try and shape and manage the impression of me that’s coming across,” David Foster Wallace told his interviewer, Rolling Stone’s  David Lipsky. “I’m hanging out with you, I can’t even tell whether I like you or not, because I’m too worried about whether you like me…. How do you learn to do this stuff? Did you go to interviewing school?”

Lipsky had to fight to convince his editor about the assignment, then had to win Wallace’s interest and trust. The story, published in 2008, received the 2009 National Magazine Award. The book, Although of Course You End Up Becoming Yourself—containing the entire trip—followed in 2010, a Times bestseller and NPR Best Book of the Year. Which lead to 2015’s The End of the Tour, with Lipsky portrayed by an awed and avid Jesse Eisenberg, and Jason Segel masterfully playing David Wallace.

“Why are we,” Wallace asks in the movie and book, “and by ‘we’ I mean people like you and me: mostly white, upper middle class or upper class, obscenely well educated, doing really interesting jobs, sitting in really expensive chairs, watching the best, you know, watching the most sophisticated electronic equipment money can buy—why do we feel empty and unhappy?”

Lipsky collected and sorted Wallace’s testimony during the rise of grunge and the everything-online generation. (“We’re gonna have to build some machinery, inside our guts, to help us deal with this. Because it’s gonna get easier and easier, and more and more convenient, and more and more pleasurable, to be alone with images on a screen,” Wallace says, “given to us by people who do not love us but want our money.”) In the book, the young writers discourse on junk food, junk movies, good books, bad relationships, loneliness, fame, and addiction.

Lipsky is a professor of creative writing at New York University and a powerful voice in American fiction (Three Thousand Dollars, The Art Fair) and nonfiction (Although of Course, Absolutely American, the forthcoming Parrot and the Igloo). Disproving the axiom that journalists make terrible interviews, Lipsky responded to my questions with enthusiasm and curiosity. We talked about Gabriel García...