The purpose of this study was to compare the most important life events reported by U.S. and Japanese centenarians. This study included a population-based sample of 239 U.S. centenarians from the Georgia Centenarian Study and 304 Japanese centenarians from the Tokyo Centenarian Study. Two open-ended life events questions were categorized and grouped into different life event domains. Several cross-tabulations were computed to investigate culture and gender differences in most important life event domains. Next, four configural frequency analyses were conducted using Neuroticism, Extraversion, and the first most often mentioned life event domain for each sample (i.e., marriage and historical life events). Results suggest that events related to marriage were the most frequent important event domains mentioned by U.S. centenarians. The Japanese sample was more likely to report historical events. Men from the U.S. were more likely to report events related to work and retirement compared to U.S. women, and U.S. women reported events related to family as the most important life events when compared to U.S. men. Japanese women considered events related to marriage, death and grief as the most important life events when compared to Japanese men. In addition, Japanese men reported events related to work and retirement as the most important life events. A cross-cultural difference was found in life events: U.S. centenarians were more likely to mention positive experiences related to marriage and children, whereas Japanese centenarians reported mostly negative and traumatic experiences such as historical, death/grief, and work/retirement events.