In real life, A Reckoning is based on playwright Eugene O'Neill's The Iceman Cometh, featuring a similar story and characters (this play, in turn, is thought of as inspired by Maxim Gorky's The Lower Depths, after which the tavern the Lower Depths is named.
His name is a reference to Oliver "Doolittle" Lynn, the husband of Loretta Lynn (on whom Junebug is based). Doolittle Lynn was also known as "Mooney," due to the fact he made a living selling moonshine, illegally-distilled alcohol. His name is also a possible reference to Hilda "H.D." Doolittle, an American Imagist poet.