This study examines the themes of fragility and disillusionment in Tennessee Williams's A Streetcar Named Desire and Arthur Miller's Death of a Salesman. Through the tragic figures of Blanche DuBois and Willy Loman, both plays explore the psychological vulnerabilities and social pressures that contribute to their ultimate downfalls. The characters’ adherence to illusions—whether regarding their personal worth, past lives, or societal roles—emerges as a central motif, revealing the destructive effects of such delusions in an ever-changing world. By analysing character development, symbolism, and socio-cultural critique, the paper offers a comparative study that underscores how these works examine the complexities of human aspiration and failure. The analysis highlights the characters’ inability to reconcile their ideals with the harsh realities of their respective environments, ultimately resulting in their disillusionment. The study also considers how both plays critique the socio-economic structures of their time, emphasizing the tension between individual dreams and societal expectations. Through this exploration, the paper underscores the continued relevance of these works in modern discourse, where themes of fragility, disillusionment, and the conflict between aspiration and reality remain resonant.