The typical post-World War II nuclear family was sidelined during the political and societal turmoil of the 1960s. Due to divorce, remarriage, and blended families, the 21st century has seen an increasing number of grandparents involved in their grandchildren’s lives. To celebrate Grandparents Day in September, this article examines the portrayal of grandparents and great-grandparents in selected Caldecott Medal and Honor books.