Anthocyanins and proanthocyanidins are widespread in the plant kingdom and are involved in important bioactivities, such as antioxidation. These flavonoids can reduce the risk of cardiovascular diseases, cancer, high blood pressure, hyperlipidemia, and diabetes; consequently, they are widely studied for disease prevention and treatment. In this review, we summarize recent advances in our understanding of the chemical structures, food sources, and bioactivities of these compounds. We also discuss recent developments and trends related to anthocyanin- and proanthocyanidin-derived products. This review provides insights to inform related research and inspire future studies to help realize the potential of these plant pigments.