This paper examines the theme of wounded masculinity in Ernest Hemingway's major novels, including The Sun Also Rises (1926), A Farewell to Arms (1929), For Whom the Bell Tolls (1940), and The Old Man and the Sea (1952). Drawing on feminist literary theory, psychoanalytic criticism, and cultural studies, it argues that Hemingway's male protagonists embody a paradoxical masculine ideal: men who are physically or psychologically damaged yet compelled to perform stoic toughness as a defence against acknowledged vulnerability. The paper traces how World War I trauma, patriarchal social structures, and Hemingway's own autobiographical anxieties converged to produce a literary mythology of wounded manhood that has profoundly shaped twentieth-century American culture. Through close readings of key passages and characters—Jake Barnes, Frederic Henry, Robert Jordan, and Santiago—this study reveals how Hemingway simultaneously critiques and reifies hegemonic masculinity, leaving a legacy that scholars continue to interrogate in the twenty-first century.