Crop production is the main source of food, and drought is among the most important crop production constraints in the world, particularly in sub-Saharan Africa. The use of improved cultivars can at least partly ameliorate the calamities of drought stress, and considerable investments and efforts have been made worldwide to develop drought tolerant crop cultivars. A number of improved cultivars of different crops have also been released for production in different countries. As related to the situation under normal environments, it is yet hardly possible to say that these investments and efforts have modernized the production under drought-prone environments as a whole and boosted the actual productivity as desired. Therefore, the limitations and strategic implications of past experiences made to develop drought tolerant crop cultivars needs to be synthesized in order to formulate better strategies and approaches. In this review article, the scope and impacts of drought, approaches to breeding for drought tolerance and the associated challenges and ways out of the challenges have been discussed. We believe that this review will enhance the efforts underway to meaningfully adopt plant breeding for improving crop production in the face of the changing climate.