His Memoirs of a Public Baby (1958, Faber and Faber) threw light on his early life. It is dedicated to Anna Wing, the actress and his third partner with whom he had a son, Jon, now a successful educator.
This was followed by The Lower View (1960), Living in Croesor (1962) and Vagrancy (1963). He was a heavy drinker and (at the very least) massively eccentric, living a mainly parasitic life. In his own words, he "bathed in life and dried myself on the typewriter".
In 1963, O'Connor interviewed an acquaintance, Quentin Crisp, for the BBC Third Programme. A publisher who happened to hear the broadcast was impressed by Crisp's performance, and as an indirect result of O'Connor's interview, Crisp ended up writing The Naked Civil Servant.
He married the American heiress Panna Grady in 1967 and settled with her in France.
Quentin & Philip by Andrew Barrow is a joint biography of O'Connor and Quentin Crisp.