Xia Jing Shan has dedicated his life to Buddhist portraiture, Zen philosophy, and the art of Chinese calligraphy, and his art combines ancient and natural elements in a masterful way, with Zen teachings and inspiring, enlightening notions conveyed through his paintings and calligraphic art. Xia has created several paintings of Hanshan and Shide using the “subtraction” style, whereby he ingeniously depicts these Zen paintings. It is said that Hanshan and Shide were poets and monks from the Tang dynasty, whom are also identified as a Buddhist “huohe” (harmonious union, a harmony of the community of monks) and regarded to be incarnations of the Bodhisattvas Mañjuśrī (Monju) and Samantabadhra (Fugen). The images of these two characters have been refined to showcase different religious features. Inheriting the legacy of Zen Buddhism passed down from Song and Yuan dynasties when the religion was highly prevalent, Xia’s paintings of Hanshan and Shide showcase simple brushwork to convey the Zen qualities exuded by these venerated Buddhist and Taoist figures, with interesting Zen elements presented through the depicted subject matters and the artistic style. This paper includes studies conducted on Hanshan and Shide paintings found in Archives of Xia Jing Shan’s Buddha Paintings published in 2013 by Beijing Arts and Crafts Publishing House and also artworks from the Jing Shan E-Gallery launched by the Xia Jing Shan Arts and Cultural Foundation. The ink expressions, implications, and theories shown on Xia’s paintings are multilayered in their ink brushwork, with Zen theories conveyed through the inscriptions. The characters are depicted in a style reminiscent of Southern Song dynasty painter Liang Kai’s prominent subtraction brushwork, which highlights swift strokes and splayed-bristle techniques, with ink and water applied to create wash effects to result in free and flowing ink expressions. The characters are depicted to appear comical and wild, with unkempt hair and vivid and joyful expressions illustrated on the Zen monks. The paintings and calligraphic inscriptions are created with vibrant and poetic ink expressions, with Hanshan and Shide portrayed in plain cotton garbs depicted in a simple and sincere manner. The intrinsic nature of Zen is a wisdom that transcends beyond one’s inherent existence, and Xia uses ink brushwork to express Zen teachings, with the ink expressions leading towards an enlightened state of Zen through art.