Kara Walker ’s Boo-Hoo (2000) is a seminal signed limited edition linocut that exemplifies the artist’s role as one of the most incisive political artists working today. Rendered in stark black against a pale ground, the composition presents a monumental silhouetted female figure whose exaggerated tears transform into whip-like forms, collapsing the boundary between emotional expression and physical violence. Drawing on the visual language of 19th-century silhouette portraiture and antebellum imagery, Walker reclaims and subverts these historical forms to expose the enduring structures of racial and gendered power in American history. In Boo-Hoo , sentimentality becomes destabilizing rather than consoling: grief turns confrontational, vulnerability merges with aggression, and the figure oscillates between victim and perpetrator. This ambiguity is central to Walker’s political artwork, forcing viewers to confront uncomfortable histories rather than passively consume them. Commissioned and published by Parkett in 2000 and printed by Maurice Sanchez at Derrière L’Etoile Studio, New York , this linocut underscores Walker’s sustained engagement with printmaking as a direct and democratic medium for political critique. The physicality and scale of the fine art print intensify its impact, reinforcing the immediacy and urgency of its subject matter. Issued in a signed and numbered edition of 70 plus artist’s proofs and documented in Parkett no. 59, Boo-Hoo stands as a defining example of Kara Walker’s politically charged practice, in which history, race, and power are confronted through uncompromising visual form.