The ongoing universality of the theme of illusion and reality allows for it to be discussed afresh and to be reinterpreted according to the outlook of the time. This theme forms a link between Sophocles’ Oedipus the King and Albee’s Who’s Afraid of Virginia Woolf?. One is a Greek tragedy showing the helplessness of man in the face of celestial powers that are too strong for him, and the other is an American twentieth century play showing the ineffectiveness of man in an absurd world. Through the study of the conveyance of illusion and reality in both plays, this paper aims to show how this theme connects the two plays, and yet how it still stands as a sign of their different times. Sophocles’ play delivers the message that order could be restored when man acknowledges the reality of his limits rather than taking a hubristic delusionary path. Albee’s play shows that human compassion could be attained through admitting one’s reality instead of adopting a deluded life. The resolution to face reality requires bravery in the difficult worlds of the two plays, but submission to it is shown to be the only way ultimately offered man. Both plays end on a melancholic note due to the harsh reality with which the characters finally come face to face.