Harold Pinter was the most influential, provocative, and poetic dramatist of his generation. Moreover, he was best remembered by his ability to create dramatic poetry out of everyday speech, which was considered as his greatest contribution to modern drama.
     The greatest power of most of Pinter's plays originates from the truth of a character's feeling that always lies in the unspoken words or in what is known as “Pinter's pauses". For Pinter, the drama is not inherent in the speech of the characters existed on the stage but rather in the unknown world in the invisible end of most of his plays.
          The main aim of this research is to highlight the progress of Pinter's dramatic writing from the modernist features, which were familiar with the audience at that time, to the postmodern principles in order to portray the dilemma of the contemporary man. Through his innovative Pinteresque technique, Pinter reveal the typical postmodern human predicament in his dramas. Strikly speaking, Pinter proceedded from the modernist tradition of the early Twentieth Century to a postmodernist mode, necessitated by his pseudo-realistic handling in the 1960s.
     The selected plays represent the three stages of Pinter's progress as a dramatist. The Room represents the comedy of menace, Betrayal is a memory play, One for the Road introduces an explicit political theme. On the other hand, the three selected plays, serving the main aim of this research, are ideal examples for the progress of Printer's dramatic writing from the aesthetics of modernism to the main principles of postmodernism. Those notable plays highlight how Pinter employs the modernist elements to serve his presentation of the postmodern human life. Hence, those selected masterpieces elaborate the unique Pinteresque approach that contributes to the progress of drama from modernism to postmodernism.