This article reexamines Eugene O’Neill’s first Pulitzer Prizes, for Beyond the Horizon and “Anna Christie.” These prizes, awarded in such swift succession almost exactly a century ago, positioned O’Neill as the United States’s premier dramatist and also established the model for critically acclaimed American drama. O’Neill’s early successes are about misbegotten outsiders, whose lives as farmers, sailors, immigrants, and sex workers convey a diverse and realistic American experience in contrast with the fantasies of vaudeville and melodrama. Yet O’Neill depicts these characters without indicting the systemic injustices that force them into their outsider roles. The plays, like O’Neill himself, are cautiously and imperfectly progressive. A century after these awards, we can see how O’Neill continues to shape American drama and how recent dramatists awarded the Pulitzer Prize continue to build upon O’Neill’s model of social and cultural inclusivity.