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In April 2010, Lipsky published Although of Course You End Up Becoming Yourself, about a five-day road trip with the writer David Foster Wallace. In Time Magazine, Lev Grossman wrote, "The transcript of their brilliant conversations reads like a two-man Tom Stoppard play or a four-handed duet scored for typewriter." The Atlantic Monthly called the work, "far-reaching, insightful, very funny, profound, surprising, and awfully human"; at National Public Radio, Michael Schaub described the book as "a startlingly sad yet deeply funny postscript to the career of one of the most interesting American writers of all time." Newsweek noted, "For readers unfamiliar with the sometimes intimidating Wallace oeuvre, Lipsky has provided a conversational entry point into the writer's thought process. It's odd to think that a book about Wallace could serve both the newbies and the hard-cores, but here it is." Publishers Weekly, in a starred review, described the book as "rollicking" and "compellingly real," the Wall Street Journal as "lovely," and Laura Miller in Salon called it "exhilarating." The book was a New York Times best-seller and an NPR Best Book of the Year. A film adaptation of the book, The End of the Tour, was released in July 2015, with Academy Award-nominated actor Jesse Eisenberg portraying Lipsky and Jason Segel portraying Wallace.

Lipsky received a National Magazine Award in 2009. He is a contributing editor at Rolling Stone. He currently lives in New York City.

Lipsky's non-fiction book Absolutely American (2003) was written after the author spent four years living at West Point. The book's genesis was a piece Lipsky wrote for Rolling Stone—the longest article published in that magazine since Hunter S. Thompson's Fear and Loathing in Las Vegas. As Newsweek noted, composition of the book required "14,000 pages of interview transcripts, 60 notebooks and four pairs of boots"; the magazine called the book "addictive," and Lev Grossman in Time wrote that it was "fascinating, funny, and tremendously well-written. Take a good look: this is the face America turns to most of the world, and until now it's one that most of us have never seen." In the New York Times Book Review, David Brooks called the book "wonderfully told," praising it as both "a superb description of modern military culture, and one of the most gripping accounts of university life I have read." The work was a New York Times best-seller and a Time magazine Best Book of the Year. Lipsky sold the motion picture and television rights to the story to Disney.

Lipsky's work has appeared in Rolling Stone, Harper's Magazine, The New Yorker, The New York Times, Details, This American Life, and All Things Considered. He received a GLAAD Media Award for journalism in 1999. In 2009, he received the National Magazine Award.

His novel The Art Fair (1996), a bildungsroman composed of a number of autobiographical elements, tells the story of Richard and Joan Freely—a New York artist and her precocious son. The novel won rave reviews and was named a Time Best Book of the Year. The work earned Lipsky comparisons to writers Michael Chabon and Harold Brodkey. The New York Times called the novel "riveting," The New Yorker described it "a darkly comic love story," People noted, "Lipsky's portrayal of the art world is unblinking, his portrayal of the ties between parent and child deeply affecting"; the critic Francine Prose called the book's "Darwinian" milieu a "testament to Lipsky's skill" and James Atlas wrote "the novel perfectly captures artists and dealers, the tiny gestures of cruelty that confirm or withhold status." The trade publication Library Journal summarized, "The praise has poured as thick as impasto."

As a graduate student, Lipsky wrote the stories that would become his first book, Three Thousand Dollars (1989). The novelist John Gregory Brown explained, "It was kind of apparent that Lipsky might have the brightest future of anyone [here]." The book was well received upon publication, with the trade publication Booklist summarizing, "Critics loved Lipsky's short story collection"; the author was seen to possess "unlimited depth and range of vision," and the stories were compared to the works of F. Scott Fitzgerald. The Los Angeles Times, while noting the book's "astonishing insights into the New York art world," concluded, "Lipsky has given his contemporaries a general autobiography, one that will fit the majority with only minor adjustments."

As an undergraduate, Lipsky published his story "Three Thousand Dollars" in The New Yorker. It was selected by Raymond Carver as one of the Best American Short Stories of 1986. Carver was surprised by the author's youth, noting in his introduction,

David Lipsky was born in New York City, and is the son of the painter Pat Lipsky. He graduated from Stuyvesant High School in 1983 and matriculated at Bennington College. Lipsky transferred in his sophomore year to Brown University, where he graduated magna cum laude and studied with the writer John Hawkes. He received his M.A. from Johns Hopkins University, where he studied with the novelist John Barth. Lipsky currently teaches creative writing at the M.F.A. program at New York University.

David Lipsky (born July 20, 1965) is an American author. His works have been New York Times bestsellers, New York Times Notable Books, Time and NPR Best Books of the Year, and have been included in The Best American Magazine Writing and The Best American Short Stories collections.