Children’s literature has great potential for starting conversations about human diversity and ability. In this paper, books from the Dolly Gray Children’s Literature Award are provided as a model for using children’s literature to talk about disability in the classroom. We present questions teachers can ask and highlight some considerations to note in choosing children’s literature for the classroom. Key considerations include family roles, cultural diversity, voice, self-determination, and portrayal of disabilities. We also offer sample discussion guides and activities for using books in early childhood, elementary, and secondary settings. Our hope is that teachers will find this helpful in making decisions on choosing appropriate literature and in facilitating thoughtful and meaningful discussions about disability.