Taking an international comparative perspective, this paper deals with driving forces of and potential obstacles to the labor market participation of older workers. It focuses in depth on four case studies that appear to be prototypical for different contexts. Given the high variance of cultures of work and welfare state systems in Europe and its neighbouring countries, Germany, Israel, Italy and Sweden were selected with the aim of examining the development and situation of older workers in great detail. Each country stands for a specific configuration, e.g. because it may represent a trend reversal, a continuously outstanding performance or lasting problems. The cases also include information on pension reforms and approaches to better manage aging workforces. In face of the different country situations, it becomes obvious that one size of policies does not fit all. Independent of national policies, employability over the life cycle requires more attention. Regarding future developments, several domains of organizational practices are indispensable for appropriately managing an aging workforce, including skill improvement and a healthy work environment.