A City of Sadness (Chinese: 悲情城市; pinyin: Bēiqíng chéngshì) is a 1989 Taiwanese historical drama directed by Hou Hsiao-hsien. It tells the story of a family embroiled in the "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 and recent emigres from the Mainland 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 takeover of Taiwan, which had been relinquished following Japan's defeat in World War II, and the first to depict the February 28 Incident of 1947, in which thousands of people were massacred by the KMT.

A City of Sadness was the first (of three) Taiwanese films to win the Golden Lion award at the Venice Film Festival, and is often considered Hou's masterpiece. The film was selected as the Taiwanese entry for the Best Foreign Language Film at the 62nd Academy Awards, but was not accepted as a nominee.This film is regarded as the second installment in the Wu Nien-jen trilogy as well as the first installment in a loose trilogy of Hsiao-Hsien's films that deal with Taiwanese history, which also includes The Puppetmaster (1993) and Good Men, Good Women (1995). These films are collectively called the "Taiwan Trilogy" by academics and critics.