Sadallah Wannous (1941-1997), the leading Syrian dramatist, reflected in his plays the condition of the downtrodden fellow-countrymen. He captured the essence of the average Syrian citizen, not as an innately timid soul, but as one cowed by political and economic oppression. This paper provides a case study of two anti-heroes; Hanzala in Hazala's Journey from Unawareness to awakening (1978) and Farouk in A Day of Our Time (1993), who go on two journeys of discovery of the roots of their problems. The journeys in both cases lead to awakening and protest. This study attempts at analyzing the significance of the underdog figure in the light of dramatic and textual analysis and Wannous's own views communicated in his non dramatic writings and the interviews he gave in his lifetime. As a result, the author of this paper concludes that Wannous' anti-heroes delineate the collective psyche of the oppressed civilians. The awakening process delineated in the said plays is an attempt to raise political awareness in the masses of Wannous’s audience.