The National Portrait Gallery’s triennial Outwin Boochever Portrait Competition celebrates excellence in the art of portraiture. As the realization of a gift made by Virginia Outwin Boochever (1920–2005) to the Smithsonian, both the competition and this exhibition demonstrate the power of one individual to make a transformative impact. The 42 portraits on view were selected through an open call that garnered more than 2,700 entries from artists working across the United States and Puerto Rico. The artists responded with works that engage contemporary society, many providing new insights into the unprecedented reality we have experienced in the time surrounding the COVID-19 pandemic.