Much of Wolfe's work is satirical and centres on the counterculture of the 1960s and issues related to class, social status, and the lifestyles of the economic and intellectual elites of New York City.

Wolfe began his career as a regional newspaper reporter in the 1950s, achieving national prominence in the 1960s following the publication of such best-selling books as The Electric Kool-Aid Acid Test (an account of Ken Kesey and the Merry Pranksters) and two collections of articles and essays, The Kandy-Kolored Tangerine-Flake Streamline Baby and Radical Chic & Mau-Mauing the Flak Catchers.

He majored in English, was sports editor of the college newspaper, and helped found a literary magazine, Shenandoah, giving him opportunities to practice his writing both inside and outside the classroom.

Wolfe's undergraduate thesis, entitled "A Zoo Full of Zebras: Anti-Intellectualism in America," evinced his fondness for words and aspirations toward cultural criticism.

Wolfe abandoned baseball and instead followed his professor Fishwick's example, enrolling in Yale University's American studies doctoral program.

[8] A biographer remarked on the thesis: "Reading it, one sees what has been the most baleful influence of graduate education on many who have suffered through it: It deadens all sense of style.

The editors of the Herald Tribune, including Clay Felker of the Sunday section supplement New York magazine, encouraged their writers to break the conventions of newspaper writing.

[12] Wolfe attracted attention in 1963 when, three months before the JFK assassination, he published an article on George Ohsawa and the sanpaku condition foretelling death.

[13] During the 1962–63 New York City newspaper strike, Wolfe approached Esquire magazine about an article on the hot rod and custom car culture of southern California.

[14] This was what Wolfe called New Journalism, in which some journalists and essayists experimented with a variety of literary techniques, mixing them with the traditional ideal of dispassionate, even-handed reporting.

"[16] Wolfe also championed what he called "saturation reporting," a reportorial approach in which the journalist "shadows" and observes the subject over an extended period of time.

This account of the Merry Pranksters, a famous sixties counter-culture group, was highly experimental in Wolfe's use of onomatopoeia, free association, and eccentric punctuation—such as multiple exclamation marks and italics—to convey the manic ideas and personalities of Ken Kesey and his followers.

This book published pieces by Truman Capote, Hunter S. Thompson, Norman Mailer, Gay Talese, Joan Didion, and several other well-known writers, with the common theme of journalism that incorporated literary techniques and which could be considered literature.

Wolfe wrote on popular culture, architecture, politics, and other topics that underscored, among other things, how American life in the 1960s had been transformed by post-WWII economic prosperity.

His defining work from this era is The Electric Kool-Aid Acid Test (published the same day as The Pump House Gang in 1968), which for many epitomized the 1960s.

Following their training and unofficial, even foolhardy, exploits, he likened these heroes to "single combat warriors" of a bygone era, going forth to battle in the Space Race on behalf of their country.

Wolfe synthesized what he construed as the views of Alfred Russel Wallace and Chomsky on the language organ as not being a product of natural selection to suggest that speech is an invention that is responsible for establishing our humanity.

To overcome his writer's block, Wolfe wrote to Jann Wenner, editor of Rolling Stone, to propose an idea drawn from Charles Dickens and Thackeray: to serialize his novel.

[25] The frequent deadline pressure gave him the motivation he had sought, and from July 1984 to August 1985, he published a new installment in each biweekly issue of Rolling Stone.

The book was a commercial and critical success, spending weeks on bestseller lists and earning praise from the very literary establishment on which Wolfe had long heaped scorn.

An initial printing of 1.2 million copies was announced and the book stayed at number one on The New York Times' bestseller list for ten weeks.

"[28] His comments sparked an intense war of words in the print and broadcast media among Wolfe and Updike, and authors John Irving and Norman Mailer, who also entered the fray.

He published his third novel, I Am Charlotte Simmons (2004), chronicling the decline of a poor, bright scholarship student from Alleghany County, North Carolina, after attending an elite university.

The novel won a Bad Sex in Fiction Award from the London-based Literary Review, a prize established "to draw attention to the crude, tasteless, often perfunctory use of redundant passages of sexual description in the modern novel".

[citation needed] Wolfe wrote that his goal in writing fiction was to document contemporary society in the tradition of Charles Dickens, Émile Zola, and John Steinbeck.

[33] According to the publisher, Back to Blood is about "class, family, wealth, race, crime, sex, corruption and ambition in Miami, the city where America's future has arrived first.

"[37] Critic Dwight Garner praised Wolfe as "a brilliantly gifted social observer and satirist" who "made a fetish of close and often comically slashing detail" and was "unafraid of kicking up at the pretensions of the literary establishment.

Wolfe describes the characters' thought and emotional processes, such as fear, humiliation and lust, in the clinical terminology of brain chemistry.

[49] Wolfe's views and choice of subject material, such as mocking left-wing intellectuals in Radical Chic, glorifying astronauts in The Right Stuff, and critiquing Noam Chomsky in The Kingdom of Speech sometimes resulted in his being labeled conservative.

[2][67] The historian Meredith Hindley credits Wolfe with introducing the terms "statusphere", "the right stuff", "radical chic", "the Me Decade" and "good ol' boy" into the English lexicon.