By the 1950s, Humphrey had escaped his origins: He was thought of as a member of the glittering literati of the northeast, and Vogue magazine featured him in its “gallery of international charmers among men,” along with Marlon Brando, Sir Edmund Hillary, Leonard Bernstein, and John F. Kennedy.
Unlike Truman Capote and Norman Mailer, and despite his profound desire to be remembered for his literary contributions, Humphrey made very little effort to promote himself.
Humphrey moved to Chicago and then New York City with his play Ambassador Ben in hand to see if he could become a Broadway success.
There Humphrey worked on the farm belonging to Donald Peterson, the producer and director of The Ave Maria Hour on WMCA radio.
Humphrey secured a teaching post at Bard College in Annandale-on-Hudson, New York in 1949, the same year he married Dorothy Feinman Cantine,[2] a painter of considerable talent who had a daughter Toni.
He taught at Bard until 1958 when the success of his first novel, Home from the Hill (1958), and its 1960 film adaptation, gave him enough money to quit teaching and devote himself to writing full-time.
His second novel, The Ordways, was reviewed by the 'New York Times as "Funny, vivid and moving, this is a fine piece of work and a delight to read," and was compared to the writings of William Faulkner and Mark Twain.
Humphrey’s first novel set outside the South, it portrays a man named Ben Curtis on the day he reenters life after a two-year descent into darkness resulting from his son’s suicide.
They also display his relationship with other writers, including Katherine Anne Porter, Theodore Weiss, and Rust Hill.
Jonathan Yardley, writing in The Washington Post (issue of 5 July 1992), remarked of Humphrey: "Minor, but interesting and admirable.