Self-Portrait on the Borderline Between Mexico and the United States by the Mexican artist Frida Kahlo reveals a multitude of insights. This paper assesses how the nuances embodied in the painting serve as critical clues to comprehend Frida Kahlo’s personal experiences, Mexican culture, and the approach of discovering the contextual background through the work of art. Beginning with a detailed formal analysis of the portrait, this paper further explores it by making connections with contextual evidence. Through timely reference to Frida Kahlo’s political stance, cultural identity, and health, the paper demonstrates how the painting proffers insight into both the artist’s life and Aztec culture