This paper establishes the pivotal role and irreplaceable value of painting in the technology-driven, image-saturated contemporary culture today. Particularly in my work, painting old childhood photographs creates a contemplative platform where I can deconstruct and reconstruct relics of my formative past as means of better understanding my multicultural upbringing. Inspired by both Chinese Communist propaganda posters and the ’85 New Wave Contemporary Chinese Art Movement, my senior project confronts the façade of perfection staged in Chinese family portraits through convoluted layers of imagery and Chinese text that build up the painting. The amalgamation of bold outlines, expressive brushstrokes, and disciplined grids, challenges the stifling values of discipline, order, and homogeneity in traditional Chinese culture.