Trow was born in an upper middle-class family in Greenwich, Connecticut. His father was a newspaperman. He expected Trow to carry on the tradition of Franklin Roosevelt: that is, to be responsible for maintaining the civic virtues in American culture. Trow took on that responsibility, but rebelled against it late in life. (His 1999 book, Media Studies, 1950-1998, is his declaration of independence from this obligation.) Trow studied at the Phillips Exeter Academy, and graduated from Harvard University in 1965. There, he was president of the Harvard Lampoon. He later served as an editor for its offshoot, the National Lampoon, working with young humorists like Michael O'Donoghue. He served on active duty in the U.S. Coast Guard. In 1966, Trow took a position at The New Yorker, writing articles for the magazine, especially in the section "The Talk of the Town," and contributing short fiction. He worked under editors William Shawn (1951-1987) and Robert Gottlieb (1987-1992), whom he saw as mentors.

In 1994, when new editor Tina Brown invited Roseanne Barr to oversee a special issue on women, Trow quit the magazine in protest. He abandoned the house he was building in Germantown, New York, and traveled around North America, living in Texas, Alaska, and Newfoundland. Several years before his death, he moved to Naples, Italy. He died there in 2006, officially of natural causes.

Trow's identity was complex. In My Pilgrim's Progress, the half-Irish, half-WASP Trow writes, "this book is the story of an Irish soul (mine by right) struggling with a great deal of Angle-Saxon cultural information (also mine by right...)" Trow was a homosexual attracted to working-class men. Trow was also socially ambitious: throughout his life, he was "striving to be part of the '10 percent of people at Harvard who wear tuxedos to their own little events in their own little buildings and you can see them out on their balconies with their tuxedos and their often very beautiful girls who are also similarly there from the Vanderbilts and the Astors.'"

Throughout his career, Trow analyzed mainstream American cultural institutions to understand how the culture had changed from the newspaper-reading, eastern Establishment-dominated world of his childhood in the 1940s and early '50s, to the ahistorical, tabloid sensibility born in the Jazz Age and propagated by television.

Trow's reputation rests on his long nonfiction. These works have received mostly positive reviews. Highly literate readers, as well as reviewers in newspapers like The New York Times and The Washington Post, have been thrilled by Trow's brilliant and prophetic insights; wide-ranging references to serious and pop culture; and aphoristic, sometimes post-modern literary style. But the appeal and value of Trow's work can be difficult to communicate, because the style "in its very essence resists summary. Summary, of course, flees from detail, whereas for Trow the details are the notes without which there is no song." Some critics have found these works impenetrable and elitist; some argue that Trow's nostalgia for the pre-television era was misplaced, because the subsequent civil rights movements had made American culture more democratic.

Trow's only novel, The City in the Mist, (1984) did not impress critics. They were put off by its minimalist style and lack of plot, narrative momentum or involving characters. The book, which moves from the mid-19th century to the present, tracks the energy in three intertwined families, from the masculine vitality of a thuggish Irish immigrant to the weak flame of his elderly bachelor grandson, who lives on his income in two rooms in New York City, and spends his time caring for his clothes and going out into what remains of Society. The central concerns of the novel - the decline of masculine energy and the replacement of masculine social authority by feminine social authority - Trow later addresses explicitly in My Pilgrim's Progress.

Within the Context of No Context, which was edited by New Yorker editor William Shawn, was published in book form in 1981 accompanied by Trow's profile of music mogul Ahmet Ertegün. In 1997, "No Context" was reprinted with a new introductory essay, Collapsing Dominant.

In "No Context," Trow pointed out the role of television in the destruction of American public culture and Americans' sense of history. "Middle-distance" institutions that had long given Americans' lives real contexts (such as fraternal organizations, bowling leagues, and women's clubs), had disappeared as people stayed home to watch television. Their replacements, television shows, were false contexts designed to be just compelling enough to keep people watching. What remained as real contexts for Americans to live in were "the grid of two hundred million" (the U.S. population at the time) and "the grid of intimacy" (the immediate family). Celebrities had a real life in both grids, and only they could now be complete. Deprived of real context, everyone else now wanted to be celebrities themselves.

Another major insight: As television marketers segmented the viewers into demographically defined groups, and pitched advertisements and shows to particular niches, viewers for the first time learned to see themselves as part of an age-related demographic group rather than as part of a linear flow of people from the past into the future. In consequence, demography had replaced history as the default context for understanding the world. Things were now valued not on an absolute scale, but by discovering if one was in tune with one's group. Trow illustrates this point with a reference to Family Feud, where a contestant was asked to guess "what a poll of a hundred people had guessed would be the height of the average American woman. Guess what they guessed. Guess what they guessed the average is."

"No Context" ends with a narrative memoir of Trow’s experiences working two summers as a guide at the 1964 New York World's Fair. His summary of the Fair: "At the Fair, one could see the world of television impersonating the world of history.”

"No Context" remains a touchstone for many intellectuals, and is taught in university media studies classes. In an obituary for Trow, the novelist and screenwriter Michael Tolkin is quoted as saying that "No Context" is no longer fashionable because "It's not a polemic for change. It's just a cold description of where things are going. There aren't many books that are unafraid to be that negative."

In his essay The Harvard Black Rock Forest, Trow criticizes another mainstream American institution, Harvard University (which he had attended). The Black Rock Forest, 50 miles north of New York City along the Hudson River, had been donated to Harvard as a nature preserve for scientific studies. Trow writes about the Harvard administration's indifference to the property except as a profit opportunity, and its eventual rescue and dedication to educational nature studies.

A memoir and prequel to "No Context," My Pilgrim's Progress: Media Studies, 1950-1998 analyzes the cultural world of the United States in the Fifties, at the transitional time when television began to take over American culture. The book is written in a conversational style, sometimes transcribed from audiotapes. Trow "swirls" between pop and mainstream cultural icons, such as Doris Day, Alfred Hitchcock, Elvis Presley, and Dwight D. Eisenhower. The book cover has a photograph of President Eisenhower, whom Trow admired as "the guy of guys". Trow asserts that the models of masculine adulthood presented to his Baby Boomer generation by the official mass culture were so out of date or irrelevant that being in/on/with television (and adopting an ironic attitude to one's self) was the only possible choice.

Reviewers of Progress have generally found it insightful and worth reading, although a lesser literary achievement than "No Context." Some reviewers have been put off by what they see as haughtiness or elitism in Trow's repeated statement of authority, "You'll have to trust me on that one."

According to a close friend, Trow was "extremely upset" by the critical reception of Progress. After that, he only published one known article, a critique of television news anchor Dan Rather.