The inspiration and influence of Buddhism on the aesthetics of calligraphy is both deep and broad. This article attempts to cut into and further lead into the "middle way" through the basic Buddhist concepts of "form" and "emptiness." Through the examination of the meanings of "material existence" and "observing emptiness," the common connections they have with calligraphy were explored, ultimately discovering that there is a considerable correlation between the three components of material existence-"color," "shape," and "form"-and the visual expressions of calligraphy-"long, short, square, round, thick, thin, bright, and dark," as well as "bending, stretching, selecting, rejecting, moving, abiding, sitting, and reclining." In addition, the practice of calligraphy, from copying the masters to independent creation, has a different approach compared to the principles of "non-form, momentary illusive form, and form produced by meditation," but subtly shares the same results. Moreover, the observation of "emptiness" and the mental state of the art of calligraphy are intimately connected, especially in "entering the stroke" and "exiting the stroke." If the meaning of "emptiness is form' is appreciated, then the attachment of painters to "appearance" will be more easily transcended, reaching the state of "turning from the appearance to the spirit." Furthermore, "turning from the appearance" does not mean totally doing way with all appearances, so the concept of "emptiness is form" can remind us that in a painting, "the unpainted is as important as the painted." There is no need to only see one facet. This is how to deeply experience and grasp the harmonious principle of the "middle way" in a natural way. To take it further, the "slanted/upright, light/heavy, fast/slow, smooth/rough, curved/straight, hard/soft, bright/dark, thick/thin, dry/wet, front/back, sparse/dense, and tight/loose" principles of opposition and agreement can be freely used, and painters who attain this realm will find success.