The number of older adults living alone in Western societies has steadily increased. Despite this trend, little is known about the overall experience of this population. In this article, I examine the condition of living alone in old age in urban America by drawing upon two years of participant observation and ethnographic interviews with older Americans living alone, as well as with participant observation. Findings contribute to the literature on inequality, with particular attention to the theory of cumulative disadvantage over the life course. First I reveal the reasons that make living alone in old age a unique condition. Then I discuss four profiles of older adults living alone based on observed empirical patterns: the resourceful, the precarious, the segregated, and the gated elite. A comparison of these profiles suggests that intra-cohort inequalities stem from the combination of resources available and degree of intergenerational integration.