Taiwanese filmmaker Hou Hsiao-Hsien brought to the screen events that had cast a shadow over a period of Chinese/Taiwanese history and had not been widely spoken about for decades with his 1989 film City of Sadness. Bearing many similarities to the Zhang Yimou film To Live, which would be released five years later, Hou's film depicts an average family striving to maintain stability in the midst of a tumultuous social and political situation. In Yimou's film, it was the Cultural Revolution; in Hou's, the period of time from 1945-1949 following the defeat of Japan in WWII, where tension built between the native Taiwanese and Chinese mainlanders, leading to the 228 Incident in 1947 and the "White Terror" - a period of political oppression led by the Kuomintang.

In the style of many of Hou Hsiao-Hsien's films, City of Sadness is a slow-moving and delicately shot art film. Each shot is well calculated, resembling the style of the legendary Ozu, to whom Hou is frequently compared. Furthermore, Hou's approach is subdued. He depicts a family dealing with overwhelming pain and loss in such a way that emotion is restrained and a quiet dignity remains. This is a distinct contrast to Yimou's film, where emotion takes a strongly present role and catharsis is much more prevalent.

Interesting also is Hou's frequent use of partially obstructed framing in his shots. Very often, scenes of dialogue are shot through doorways or with a wall blocking a portion of the frame. Thus, we maintain a distance from the action, which is unique considering many films of this nature rely on empathy with the characters to achieve a cathartic effect, and thus employ framing techniques that make us feel close to the characters. Also present is Hou's apparent fondness for the style of silent film. Like his later film Three Times, which included an entire silent cinema portion, A City of Sadness employs cuts to text (as in a silent film) to show dialogue between a deaf character and the person to whom he is talking as they write to one another.

Overall, Hou's film effectively puts a human face on a significant historic event in a way that probably influenced many later films addressing similar subject matter. However, such an approach does require a connection to the characters that is never really achieved. Although it seems that this is even intentional, it deprives the film of a certain poignancy that is present with other works, such as the aforementioned To Live and Chuan Lu's new film City of Life and Death.