<p dir="ltr">Health behaviors such as drinking and smoking are not only fundamental to health outcomes but also serve as moral signals that shape perceptions of responsibility, competence, and worth. When disapproval of these practices escalates into stigma, it produces exclusion, status loss, and discrimination that can cause or exacerbate health inequalities. Drawing on stigmatization theory and health lifestyle theory, I field a large-scale factorial vignette experiment with a diverse U.S. sample (<i>N</i> = 1,792; 10,744 vignette evaluations) to systematically compare perceptions and stigma toward seven behaviors: alcohol use, tobacco use, marijuana use, opioid use, dietary practices, physical activity, and sleep patterns. Results show that violations of proscriptive norms, especially opioid use and heavy drinking, generate strong stigma across stereotypes, devaluation, and social distance, whereas failures to meet prescriptive norms (e.g., unhealthy diet, irregular sleep) yield weaker, competence-focused penalties. Stigmatization is more contested for behaviors undergoing normative change, such as marijuana use and vaping. Although individual health behaviors explain most stigma, interactions between behaviors emerge, particularly among highly stigmatized practices, which display diminishing marginal penalties when clustered together. Health lifestyle configurations (i.e., holistic patterns of multiple behaviors) explain more variance than main-effect or interaction models, underscoring the value of a health lifestyle approach to stigma. This finding extends stigmatization theory by demonstrating how behaviors are evaluated as coherent lifestyle packages rather than isolated practices. Finally, stigma toward health behaviors shows minimal moderation by gender and behavior-specific moderation by age for select behaviors: younger opioid users are judged more harshly than older users, and evaluations of smoking and vaping shift across cohorts. Together, this dissertation provides one of the first comprehensive sociological examinations of health behavior stigma, advancing theories of stigma, health lifestyles, and the life course while illuminating how everyday practices reinforce moral boundaries and social inequalities.</p>