The Longest Summer explores dislocation caused by the transfer of sovereignty over Hong Kong, seen from the perspective of Ga Yin (Tony Ho), a former soldier displaced due to the disbanding of the Hong Kong Defence Force. He and his comrades find their options for alternative employment disappointing, and begin to plan a bank robbery. He continues to try to find a legitimate job, but the only one interested in his skills is the gangster who employs his younger brother (Sam Lee). However, Ga Yin is reluctant to commit to a new life as a soldier of the gang.

The movie effectively conveys a mood of uncertainty and anxiety about changing times, which creates a situation in which men who have spent their entire lives following orders are suddenly ready to chart their own course and take big risks, even when it conflicts with the values that they have held. Their strength is their loyalty to each other, but their trust quickly erodes due their experiences in this new world.

The story has interesting parallels to Johnny Mak's Long Arm of the Law, a tale of a tight-knit gang of robbers from China. These ex-soldiers seem less heroic and less desperate than their doomed counterparts in the earlier movie. However, the anxiety concerning illegal immigration from China common in mid-1980s films like Long Arm of the Law mirrors the anxiety over the handover found in The Longest Summer and some other mid-1990s films, and both gangs seem trapped in long-shot enterprises, unable to back off as they see their odds lengthen and betrayals occur.

The promise that director Fruit Chan showed with Made In Hong Kong pays off in The Longest Summer. The shift in focus from alienated teenagers getting in trouble for the hell of it to middle-aged men who feel threatened and betrayed by a world that has abruptly changed, causing them to do things that they would never have considered before, results in a movie that is richer emotionally, although it is less technically flashy than the earlier film. The strong lead performance by Tony Ho anchors the movie and is as impressive in its own way as Sam Lee's flashy lead performance was in Made In Hong Kong. Jo Kuk is memorable as the alienated daughter of the mob boss, trying to be tough but proving surprisingly vulnerable and sweet. Sam Lee is interesting as the younger brother, who seems to be the kind of gangster that his character in Made In Hong Kong might have become, but he is not the focus this time.

The Longest Summer is one of the highlights of 1990s Hong Kong cinema, a crime film that is also an incisive look at a changing society. Its vision of that society is dark, but it has a few rays of hope for the future.