While adult concern about gender in children’s books has made recent headlines, this discussion is far from new. As Gregory M. Pfitzer reveals, the writers and editors at Bobbs-Merrill, the publisher of the Childhood of Famous Americans book series published between 1932 and 1958, thought carefully about how their books would influence the development of their male readers. These books emphasized inspiring tales over historical accuracy and were written in simple language, with characters, dialogue, and stories that were intended to teach boys how to be successful men. But this was a specific image of American manhood. Published in an era when sociologists, psychologists, and other experts worried about male delinquency, the men envisioned in these books were steeped in Cold War racial and gender stereotypes, and questions about citizenship and responsibility. Based on deep archival research into the publication history of the series, “From Boys to Men” sheds light on current controversies on children’s books and presentations of gender diversity.