From November 14 to December 21, 2008, Groff appeared as Billy Noone, a closeted gay soldier fighting in Iraq, in the Off-Broadway production of "Prayer for My Enemy", a play written by Craig Lucas"." The production was directed by Bartlett Sher and performed at Playwrights Horizons. Ben Brantley wrote in "The New York Times" that the play is "muddle-headed" and "disconnected", but Groff "exudes the charismatic aura of distressed youth". From April 10 to May 17, 2009, Groff appeared as Gray Korankyi and Walter Riemann in the Off-Broadway production of another Craig Lucas play, "The Singing Forest", alongside Olympia Dukakis at the Public Theater. The play, directed by Mark Wing-Davey, was described by critics as "convoluted" in plot but with strong performances, praising Groff for his "natural emotional transparency helps add layers to Gray". For both performances, Groff received an Obie Award.