This was the first Taiwanese film to be shot in direct sound. Director Hsiao-hsien Hou wanted to capture the varied dialects and accents of his actors, reflecting the film's concern for the complex, heterogeneous origins of modern Taiwan.
No.5 in the Hong Kong Film Awards' List of The Best 100 Chinese Motion Pictures
As revealed in scriptwriter Chu Tien-Wen's book, the original premise of this film is the reunion of an ex-gangster (which Hou Hsiao-Hsien intended to cast Chow Yun-fat for the role) and his former lover (supposedly played by Yang Li-Hua, the top Taiwanese Opera actress in real-life) in 1970s. Hou and Chu then extended the story to involve substantial flashbacks of the calamity of the woman's family in late 1940s (where the woman was the teenage daughter of Chen Song-Yong's character). They then abandoned the former premise and instead focused on the 1940s' story.
Average shot length (ASL): 158 minutes / 222 shots = 43 seconds (some takes last over 3 minutes).
Tony Leung Chiu Wai's character was made a deaf-mute because the film used direct sound and Leung could not convincingly speak Mandarin or Taiwanese.
In 1989, Hou Hsiao-hsien's A City of Sadness, the first film to touch on the 228 Incident, a taboo subject in Taiwan, became a big hit in the theaters. As a result Jioufen, where the film was set, revived due to the film's popularity. The nostalgic scenery of Jioufen as seen in the film, as well as appearances in other media, charmed many people into visiting Jioufen. For the beginning of the 90s, Jioufen experienced a tourist boom that has shaped the town as a tourist attraction. Soon retro-Chinese style cafés, tea houses, and souvenir stores bearing the name "City of Sadness" were built.