Gregory Orr's poetry meditates upon the nature of life and death based upon his own experiences in childhood and beyond. A professor of poetry and creative writing at the University of Virginia, Orr has published consistently for more than a quarter of a century, and his work has evolved in style and substance to include a wide variety of verse techniques. Poetry reviewer Steven Cramer observed: "Blessed with the curse of fame at twenty-six, Orr became neither a one-hit wonder nor a recycler of self-derivative tunes. Instead, he has quietly attended, and attended to, his own thirty-year singing school. Burdened with the curse of 'a long story/ of torment' to tell, this mature lyricist has found, for himself and for us, the forms that affirm."

When Orr was twelve, he accidentally shot and killed his younger brother while hunting. A few years later, his mother died unexpectedly. These events shape his poetic voice as he repeatedly seeks to come to terms with his trauma. Donald Barlow Stauffer in Contemporary Poets emphasized the "burning intensity . . . compactness of language, and . . . wise placement of a striking image" that characterizes Orr's verse. Stauffer added that a "sense of change versus selfhood is central to Orr's search for a way out of a potentially crippling youthful experience toward the renewed innocence of an emotionally integrated adult." As a result, his poetry moves from confronting the pain of his childhood to becoming a confident teacher, husband, and poet.

"Orr's first two books featured the surrealism that was one of the dominant period-styles in the 1970s," wrote Charles Molesworth in the New York Times Book Review. However, Molesworth added, the poems in Burning the Empty Nests and Gathering the Bones Together possess "a wan, almost glum intensity" which distinguishes them from other poems composed in that mode. In comparison, Orr's fourth book, The Red House, "has much plainer writing, with a concentration of subjects drawn from rural Virginia. . . . It's a private, whispered poetry," noted the reviewer, who sees Orr as one of many poets "whose emotional concerns are with a personal past." Washington Post Book World contributor Alan Williamson felt that all of Orr's best poetry relives the traumatic events of his youth. " The Red House concludes this story, in the almost heartbreaking last poems of the title sequence," the reviewer commented. Williamson believed that Orr's poems about other subjects, also "tragic in tone," are among his best.

In his Poetry review of The Caged Owl, Cramer wrote: "Always a lyric poet for whom the image provides the surest access to epiphany, Orr in his figurative language evolves away from metaphor, simile, and the totemic emblem to perceived details chosen for their emotional resonance. . . . I suspect that Orr's excellent essays on poetry have helped underwrite his deepening authority." Cramer went on to describe some of Orr's poems as "small miracles of sound insight and incisive sound." A contributor to the seventh edition of Contemporary Poets concluded that Orr's poems are attractive for their "utter honesty and directness, their refreshing lack of pretension, their flashes of humor . . . and their frank, sensitive, and circumspect treatments of sexual love, sometimes set against a background of death and dissolution." Matthew Flamm, reviewing The Caged Owl for the New York Times Book Review, noted growth in Orr's work, seen primarily by "the hard-to-decipher parables giving way to a quietly observed naturalism."

In 2002 Orr published a memoir of his first nineteen years of life that deals frankly with the tragic accident that caused his brother's death as well as the family dynamics in the wake of the accident. The Blessing details Orr's private suffering as a teen and the unexpected serenity he received after discovering poetry and art. The poet told Publishers Weekly that he decided to write the memoir while witnessing his father's decline from cancer, realizing that writing would provide closure that would never be forthcoming from his father or siblings. A Publishers Weekly reviewer wrote of the work: "Orr's gripping chronicle of his troubled boyhood is alternately self-conscious, moving, and revelatory." In her Booklist critique of The Blessing, Donna Seaman concluded that Orr "has distilled the anguish of his youth right down to its holy bones."