Do self-evaluations of general health change as individuals age? Although several perspectives point to age-related shifts, few researchers have compared them. For this article, several competing hypotheses were tested using a large, nationally representative, and longitudinal data set. The results suggest two trends. First, the correspondence between functional limitations and self-rated health declines, especially after age 50. Similarly, the correspondence between various chronic conditions and self-rated health declines with age. These findings are consistent with social comparison theory. Yet, the results also suggest that the correspondence between depressive symptoms and self-rated health increases. Indeed, after age 74, the correspondence between self-rated health and some common symptoms of depression becomes stronger than that between self-rated health and several chronic, and often fatal, somatic conditions. This crossover has important implications for the detection and treatment of depressive symptoms in later life.