Comparative studies on philanthropic foundations are still in their infancy. To advance the comparative understanding, the article proposes to use two countries—the United States and Germany—as comparative cases against which to assess the main contours of foundations in other countries. Both countries have large foundations communities; yet both are rather distinct in terms of their historical development as well as in terms of their institutional characteristics, patterns, and activities. Looking at the positioning, roles, advantages, and disadvantages of foundations, the article offers a framework for their comparative study using the varieties of capitalism, welfare regimes, and the social origins classifications.