Previous literature points to events during the transition to adulthood as important in understanding criminal offending over the life course. But youth in today's inner cities are at high risk of experiencing periods of incarceration, which may compromise successful entry into adult roles. Indeed, incarceration has become so common among inner-city youth that it has been said to be a critical event during the transition to adulthood alongside transitions in education, employment, residence, marriage, and parenting. Drawing on data from the Pittsburgh Youth Study, this paper explores the place of incarceration in the transition to adulthood experiences of at-risk males. We offer a descriptive account of the relative frequency of incarceration vis-à-vis other, more traditional life events. Given the interrelationships between life events, we apply latent class cluster analysis to explore and identify typical combinations in which they occur. This allows us to present a "snapshot" of life trajectories among at-risk males at 25. © 2010 Southern Criminal Justice Association.