It has been thirty years since the publication of Leonard Pearlin’s (1989) “The Sociological Study of Stress.” This classic work left an indelible mark, shaping the way the field thinks about stressors, their emotional consequences, and the factors that influence the nature of the links between stressors and outcomes. In this essay, I dialogue with that paper—not with a comprehensive summary of the field but rather with a sharper focus on a few core themes that have inspired the direction and current parameters of my scholarship.Pearlin’s theorizing and empirical work on social roles provides a foundation for the sociological study of stress and mental health. I describe the ways his ideas about role strains have influenced my thinking and development around themes like the Stress of Higher Status model, and I propose new directions for research on topics like distributive justice. Pearlin’s ideas hold a special place in the history of social stress research—and the many intellectual puzzles that he proposed remain and provide fertile terrain for advancing knowledge. A greater integration and synthesis of theory and evidence in the sociology of mental health, sociology of emotion, social psychology, stratification and work, occupations, and organizations will help guide such innovations.