Religious conversion depends upon a doubling of character: the “authentic” sinner becomes the “authentic” penitent. Montaigne stresses the demand for true sorrow – for the life that was – in the act of repentance, as does the memento mori tradition. Though many of Shakespeare’s characters test the possibility of such a doubling, none do so more energetically than John Falstaff. The supposed war of theology and aesthetics is at its most intense here, as it seems that the knight and the playwright must choose either a spiritually acceptable hatred of life or a dramatically laudable integrity of character. Falstaff, who from The Merry Wives of Windsor through the greater Henriad, or Harry Cycle, is obsessed with the question of true confession, comes to represent the difficulty of the confession of national sins also, through the characters of Henry IV and Henry V. His ambiguous deathbed confession thus constructs a broad hypothesis of forgiveness that transcends his own story. It suggests that there is no human guarantor of true confession, including even “hatred of one’s life,” and thus the authenticity of a conversion of life must always mark a boundary between the human-world-as-theater and the transcendence of final judgment.