Historically, the study of children's art has been predominantly constructed on developmental capacities, graphic sophistication, and particular styles conceived by adults. Although these theories of classification were developed with the best of intentions, fashioned for a better understanding of young people's art, they often simplify and decontextualize the lives and works of children. Children's art, however, is a complex matter, one that is entangled with both adults' and children's presumptions, practices, and expectations. Attending to this complexity, this article explores how young children engage in art as political subjects who participate in, disagree with, and negotiate between adults' expectations and their own desires. In doing so, I draw on philosopher Jacques Rancière's homologous yet differentiated ideas of "politics" and "aesthetics," along with a painting activity of two 5-year-old boys in a kindergarten classroom, where the tensions involved with "going out of the lines" were continuously communicated during the art making.