He was a member of The Violet Quill, a gay writer's group that met in 1980 and 1981 and included Christopher Cox, Robert Ferro, Michael Grumley, Felice Picano, Edmund White, and George Whitmore.

After graduating from Harvard with a BA in English in 1965, he followed Taylor to the University of Iowa Writers' Workshop, in part to postpone "the horror of law school.

"[6][7][8][9][10] At Iowa, where Holleran's teachers included Kurt Vonnegut, Jr. and José Donoso, he formed a long-lasting friendship with fellow student Robert Ferro.

His subsequent, increasingly autobiographical novels, short stories, and essays reflect his concerns as an aging gay man and track his movements between homes in New York City, Washington, D.C., and the small town in Florida where his parents retired and where he continues to live.

Dancer from the Dance (1978) takes place amid discotheques, gay bathhouses, fabulous parties, and seedy apartments in New York City and Fire Island.

His delirium becomes a kind of saintliness; he gives love to the ugly as well as the beautiful...The Virgil who leads Malone through this inferno is an outrageous transvestite called Sutherland.

"[23] In 1983, after a fall rendered his mother an invalid, he began living full-time in Florida, but kept a rent-controlled apartment on St. Mark's Place in the East Village.

Ground Zero (1988) presented a collection of Holleran's essays, originally published in Christopher Street, written as the AIDS epidemic struck New York and decimated its gay community.

A quarter-century after its publication, Garth Greenwell in The New Yorker assessed it as "one of the most important books to emerge from the plague,"[26] and wrote:The essays combine journalistic reportage in real time with an extraordinarily refined literary sensibility, and the conjunction is startling.

As Holleran, along with the rest of gay New York, slowly realizes the scope of the catastrophe, the effect is something like reading F. Scott Fitzgerald's notes on the apocalypse.

Peter Parker in The New York Times found it "extremely well written, and in its muted way an altogether more impressive novel than Dancer From the Dance.

"[28] Alan Hollinghurst called it a "beautiful and desolating tally of what makes up a life, what images and obsessions and childlike hungers, beyond anything that it is respectable or usual to admit, haunt it and impel it and obstruct it.

"[34] The setting is again a small Florida town, and the narrator is again an aging gay man, living in the house where his late parents retired, making "their bedroom into a temple" and keepingall their possessions, undisturbed—the clothes in their closet, my mother's gowns, the madras shirts my father had bought long after he'd gotten so old they were too beautiful for his wizened face, the package of Pall Mall cigarettes he had left in the refrigerator; all of their liquor, my mother's bottles of perfume, a picture of my mother in a red high-necked dress, looking Victorian in a small oval golden frame set between a crystal statue of the Virgin Mary and a bottle of Chanel No.

"[8]Recalling Dancer from the Dance, with its "twilit languor and ambered nostalgia," Garth Greenwell in The New Yorker noted that "Holleran's clearest influences are Fitzgerald and Proust.

One of the first things I remember about Dancer from the Dance is that it lands on the notion that all of us are self-invented people, and that behind that is a difficult and somewhat concealed past, as if in coming out there's a reverse closeting that's very Fitzgeraldian.

Though the protagonists are sometimes granted different names...the major facts of their biographies are largely constant, and shared with their author: a devout Catholic childhood on a Caribbean island; military service and initiation into gay life in Heidelberg; young adulthood in New York, where the thrill of sexual freedom competed with anxiety about possibly wasting one's life; then a mostly closeted small-town existence, caring for a disabled parent, and crushing grief after that parent's death.

[26]A notable exception to this assessment is In September, the Light Changes (1999), in which many of the short stories are less essay-like and autobiographical, and more traditionally fictional and in the vein of Dancer from the Dance than Holleran's subsequent novels.

Quoting Caryn James, in 2015 Larry Kramer took the critical establishment to task, calling Holleranthe best gay writer we have today...If he were straight, his reputation would be immense.

[47] Asked by New York Magazine to name her "favorite underrated book of the past ten years," Daphne Merkin cited Grief, and, like Kramer, said that Holleran's work is under-appreciated:This slim but singularly affecting novel put in an appearance to conditional praise last June and, to my knowledge, sank thereafter without a trace.

[48]Explicitly acknowledging Kramer's complaint from 2015, with the publication of The Kingdom of Sand in 2022 Joshua Barone in The New York Times wrote a lengthy profile and appreciation of Holleran, accompanied by photographs of the novelist in the natural habitat of the small town in Florida that is so often the setting of his works.