After false-starts with Flowers of Shanghai and Goodbye South, Goodbye, I figured out how to get on Hou’s wavelength with his Red Balloon and Three Times, so now trying something from his acclaimed 1980’s period. I liked it, and could follow reasonably well despite 90% of my knowledge of Taiwan’s post-Japanese-occupation history coming from a blurry bootleg of A Brighter Summer Day. Wikipedia, help us out with context here:

It tells the story of a family embroiled in the tragic “White Terror” that was wrought on the Taiwanese people by the Kuomintang government (KMT) after their arrival from mainland China in the late 1940s, during which thousands of Taiwanese were rounded up, shot, and/or sent to prison. The film was the first to deal openly with the KMT’s authoritarian misdeeds after its 1945 turnover of Taiwan from Japan, and the first to depict the 228 Incident of 1947, in which thousands of people were massacred.

“On August 15, 1945 Japan announced its unconditional surrender. Taiwan was liberated following 51 years of Japanese occupation. The wife of older brother Lin Wen-heung gave birth to a son. They named him Kang-ming, which means Light.” Brief introductions (Wen-heung is a stocky fellow) and a photo shoot, then suddenly a woman is narrating from the mountains, introducing W-H’s brother Wen-ching as a friend of her brother. W-C (Tony Leung 1 of 2046) is deaf/dumb (this was supposedly added to the script because Leung couldn’t speak the dialect convincingly, heh), a professional photographer who communicates to customers with gestures and to our new narrator (Hinomi) with pen/paper. W-C has other brothers besides stocky eldest Wen-heung – one disappeared in the war, and the other, Wen-leung (Jack Kao of a bunch of Hou’s films), came back mad.

W-C: happy, deaf

W-L: mad

But Wen-leung gets over his condition, joins organized crime, gets himself arrested and gets the straight Wen-heung in trouble. Eventually, W-H is killed and W-L terribly beaten, other characters disappear or escape to the mountains, and W-C ends up with Hinomi – but in the epilogue, after showing him with new wife and baby, even he is arrested again, and the titles tell us “December 1949. Mainland China is lost,” when the ROC moved to Taiwan (maintaining martial law, torture and execution for 40 years) and communist PRC formed in mainland China. So the movie takes place over four years, during which it doesn’t always seem like such sadness, but it sure turns out that way in the end.

IMDB:

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 the 1970’s. Hou and Chu then extended the story to involve substantial flashbacks of the calamity of the woman’s family in late 1940’s (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.

from an excellent essay by K. Lee for Reverse Shot:

Any given scene in City of Sadness has its own internal history informing the logic of its characters’ behaviors. Hou’s sense of dramatic conflict—one that’s unique in cinema—arises when the recurring presence of the past collides against an unfolding present unknown to both the characters and the viewer. …

City of Sadness envisions a massive shift in a tiny island’s social fabric caused by forces well beyond the scope of any person, or even a community. Everyone is overwhelmed. No less than five languages are spoken in the film: Japanese and four forms of Chinese. Even Chinese viewers require subtitles when watching this film. … Perhaps due to being the first movie to deal openly with the “2-28 Incident,” or perhaps because of the Golden Lion it won at Venice, City of Sadness was the top grossing domestic film of its year. Nonetheless, there was public dismay at the oblique nature of Hou’s storytelling and the fact that the atrocities of the “2-28 Incident” are never depicted directly onscreen (despite that there are more fight scenes and onscreen killings in City of Sadness than in all of Hou’s other films combined). …

Scenes pass like clouds, loosely connected, the overall story arc not clearly in sight, and only in retrospect, with a final shot of an empty room that once held scores of family and friends, does the sum total of the film materialize, narrative, historical, emotional. Hou’s aim is nothing less than to enact how people live history—not as something happening right in front of them, but around them and beyond them, the same way then as now. In City of Sadness the horrors of the world occur almost always out of view, but it makes their presence all the more unsettlingly palpable.