The purpose of this dissertation was to understand the ways forms of literacy and cultural oppression operate in the content of the corpus of 60 books distributed by Dolly Parton's Imagination Library (DPIL) to children who entered kindergarten in the fall of 2022 from their birth to age 5. A growing number of affiliates, including many U.S. states, are providing funding for implementation of DPIL. Policymakers value DPIL's low-cost system for providing libraries to all families of young children to increase kindergarten literacy preparedness. In participating states, DPIL mails a free book and read aloud information to every registered child each month from birth to age 5. Policymakers share DPIL's intention to leverage the power of picturebooks to transform family literacy practices. Families who own picturebooks read aloud early and often, and daily read aloud habits have positive impacts on measures of children's language and pre-literacy skills. Unfortunately, picturebooks consistently misrepresent both reading and culture, which means the content of DPIL books could undermine DPIL's purpose and perpetuate negative stereotypes while potentially inculcating community-wide biases regarding both literacy and cultural identities during a vulnerable life stage for two generations. The critical content analysis of the DPIL 2022 kindergarten corpus reported in this dissertation revealed explicit and implicit representations of literacy, race, class, gender, and dis/ability. Analysis with and through a series of critical theoretical lenses revealed the ways that the discourses of power and oppression surrounding literacy and family intersected and operated within, among, and beyond the corpus. The analyses revealed diverse racial representation that disrupts the history of White dominance in children's literature accompanied by perpetuations of multiple hegemonic cultural stereotypes. Characters with dis/abilities, non-normative gender identities, or non-normative family structures were erased. Additionally, inconsistent messaging regarding books and reading was conveyed. Three inductively derived themes: reading to succeed, living the American dream, and perfecting parenting revealed complex intersections of discourses of power that resulted in oppressive childism, which operated to subjugate children and to privilege a White, middle-class, cis-gendered, heteronormative, able-bodied American norm. Critical literacy strategies and conscientization are discussed as transformative actions toward literacy equity. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]