[3] Lipsky transferred in his sophomore year to Brown University, where he graduated magna cum laude and studied with the writer John Hawkes.

[10] 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."

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.

[11] The New York Times called the novel "riveting,"[12] The New Yorker described it "a darkly comic love story,"[13] People noted, "Lipsky's portrayal of the art world is unblinking, his portrayal of the ties between parent and child deeply affecting";[14] the critic Francine Prose called the book's "Darwinian" milieu a "testament to Lipsky's skill"[15] and James Atlas wrote "the novel perfectly captures artists and dealers, the tiny gestures of cruelty that confirm or withhold status.

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.

[24] 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.

"[27] Newsweek noted, "For readers unfamiliar with the sometimes intimidating Wallace oeuvre, Lipsky has provided a conversational entry point into the writer's thought process.

"[28] Publishers Weekly, in a starred review, described the book as "rollicking" and "compellingly real,"[29] The Wall Street Journal as "lovely,"[30] and Laura Miller in Salon called it "exhilarating.

The site's critical consensus states: "Brilliantly performed and smartly unconventional, The End of the Tour pays fitting tribute to a singular talent while offering profoundly poignant observations on the human condition.

.a gift of highly intellectual discussion between two brilliant people at turning points in their lives," while also praising Jason Segel and Jesse Eisenberg.

"[38] In his review for the New York Daily News, Joe Neumaier awarded the film five out of five stars, calling it "one of the best movies of the year .

Director James Ponsoldt's smart, incisive and extraordinary drama is the kind of film that burrows into your head and leaves you illuminated about life and how to live it.

"[39] In her review for The Los Angeles Times, Sheri Linden wrote "James Ponsoldt's magnificent The End of the Tour gives us two guys talking, and the effect is breathtaking ...

With dry wit and novelistic flair, National Magazine Award winner Lipsky chronicles how harnessing electricity changed the world.

Buoyed by thorough historical research, this is a first-rate entry," adding "Humor accompanies horrific truths in this vital look at the rise of climate change denial.

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.