Over the past half-century, product-related public health crises have claimed millions of American lives. Two of these crises have been especially prominent: tobacco and opioids. In this Article, we zero in on both controversies. Like many before us, we trace how these two addictive and deadly products became widely used by the American public and analyze the myriad ways in which the products—cigarettes and prescription painkillers—are similar. From there, however, we part ways with previous analyses, as we look beyond these surface similarities to the many ways tobacco and opioids are markedly different from one another. This analysis of differences—focusing on the products’ substitutability, social utility, and price sensitivity—ultimately underscores the crushing, and easily underestimated, challenges policymakers face, to the extent they try to curb the opioid epidemic using tried-and-true supply-side mechanisms. We then turn from the crises themselves to the litigation each has generated. From a distance of two decades, we tally the successes and failures of tobacco litigation—which began in the 1950s and crested in the late 1990s—and analyze how that mixed scorecard has informed, and, going forward, ought to inform, the sprawling opioid litigation: the most complex civil action ever tackled by any American court. Finally, moving beyond this comparative analysis, we address both the future and the utility of public health litigation. Many have asked: What is the role of litigation when it comes to promoting public welfare? Harnessing lessons from both tobacco and opioids, our answer to that question offers new insights for how tort litigation complements—and, under certain conditions, can catalyze—broader regulatory strategies.