The art of Chinese calligraphy appears in diverse forms nowadays, from being an ink art with innovative creations within the traditional culture to being a unique element in new media, conceptual art, mixed media and so on under the influence of modern and contemporary art practice primarily from the West. Such diversity stems from different interpretations of the definition, purpose and philosophical origins of Chinese calligraphy and even Art itself. The professional traditional calligraphers aim to follow the vertical development of Chinese calligraphy, construing such art history in mainly two ways: calligraphy as forms, and as the representation and expression of the human mind. The former inclines to a view of formalism, where the artistic source originates from the formal aesthetics of Chinese characters and the calligraphers’ aesthetic judgment and development based thereupon, but it might eventually lead to subjectivity and blankness. The latter emphasizes the Chinese philosophical and cultural elements within calligraphy, seeing it as a way to represent and express the calligrapher’s mind. Calligraphers of this branch are yet to find ways to reflect the complexity of contemporary souls through this retroist methodology, and to establish the relationship between art and free will. On the other hand, calligraphy has evolved horizontally to fuse with other art elements because of the trends and ideas from contemporary art. Some contemporary artists look at calligraphy critically; some see it as conceptual art while endeavouring to preserve the essence of writing Chinese characters with calligraphic brush and ink. They dig deep into calligraphy and give new meanings to every stroke in it. Needless to say, calligraphy faces challenges throughout its development as a form of conceptual art like all others. Some other artists take calligraphy as a member of mixed media, applying it in artistic juxtaposition and collage alongside other materials and media, subsequently exploring the meaning and chemistry between them all. It is crucial for artists in both vertical and horizontal context to engage in conversation to enrich the substance in their works, so as to discover new perspectives and connotations in calligraphy.