There has been a notable lack of representation of disability in Western art history. Where disabilities are displayed, the artists’ intentions were often to convey moral corruption, religious infidelity, and the faults of society. Other times, the representations functioned scientifically as medical records. In fact, one of the most anatomically accurate representations of physical disability is credited to the early modern artist Hieronymous Bosch, who was known for his unfiltered commentary on the flaws of human society. Contrary to his typical surreal, vibrant, and sarcastic style, Cripples and Beggars (after 1570), a naturalistic and observational piece, offers a rare lens into how disability was portrayed during the early modern period.1 In contrast, Rachel Gadsden—a contemporary, disabled artist—foregrounds her identity as a disabled artist in her work Ubuntu (2012) and utilizes an expressive, abstract style to convey the fluidity of the disabled human form. Cripples and Beggars and Ubuntu, separated by centuries, provide a captivating shared subject for comparative analysis that transcends temporal boundaries. Cripples and Beggars provides an early explicit and moralizing depiction of physical disability as an isolating scourge while Rachel Gadsden focuses on abstract, yet recognizable human bodies in optimistic motion and community. Analysis of the varying style, medium, and intention reveals the evolved reception and, thus, depiction of disability. This transformation, from Hieronymous Bosch's Cripples and Beggars to Rachel Gadsden's Ubuntu, signifies a shift from viewing disability as a symbol of moral corruption and societal decay to an expression of identity, resilience, and community.