Mr. Udoff quit his job at ABC to write plays. His plays The Little Gentleman and The Club, won Stanley Drama Awards in 1969. His next play, A Gun Play, which centered on violence in everyday life, premiered in 1971 at the Hartford Stage Co. It then moved to the Cherry Lane Theatre for an off-Broadway production starring Tony Musante. Clive Barnes of The New York Times wrote in his review that "Mr. Udoff appears to have a happily natural affinity for the significantly absurd."
Two earlier plays, The Little Gentleman and The Club, won Stanley Drama Awards in 1969.