Sentimentalism as a genre is known for its association with melodramatic 19th-century novels, such as Stowe's "Uncle Tom's Cabin" or Alcott's "Little Women." But, as a cultural tendency, sentimentalism can be found in a range of 19th- and 20th-century cultural, social, and political phenomena, with philanthropic and educational projects chief among them. The legacy of sentimentalism in art education needs to be recalled when attempts are made to consider race in relation to K-12 art classrooms, as well as with class, disability, and gender dynamics. In this article, I make reference to the "Hampton Album," a series of photographs taken in 1900 by Frances Benjamin Johnston, and I focus on three major thinkers to begin assessing the sentimental influence in art education, and gesturing at a pedagogical approach that more thoroughly integrates the role of ongoing conflicts and the intransigence of imbalances in power.