To decode John Dunkley’s dark and sexual landscape is also to reveal a decolonial message in his broader works. Dunkley humanizes nature through both masculinizing phallic and feminizing yonic symbolism as an emancipatory tactic, thereby reflecting a culturally nuanced relationship between people and landscape. Dunkley subverts the expected in Caribbean painting, especially for foreign consumers. By bringing nature to life, his paintings offer subversive anti-colonial themes, too, waiting for decipherment. This paper will examine Dunkley’s use of erotic imagery, arguing that the painter’s sexual landscapes, through layered poetics and symbolism, ultimately served to challenge every day oppressions in colonial Jamaica.