“For the poor life is a punishment” according to Henry (Andy Lau Tak-Wah), the embattled hero of Kent Cheng Jak-si’s Dragon in Jail (獄中龍), a subdued heroic bloodshed offshoot in which a poor boy and rich kid meet in juvie and become best friends for life even though fate seems to have very different paths in store for them. Less a critical expose of the cruelties of an increasingly stratified society than an ode to intense male friendship, Dragon in Jail puts its hero in a different kind of cell as he tries to escape the triad net but finds himself ensnared by past crime and present rage.
Rich kid Wayne (Kenny Ho Ka-King) ends up in a reformatory for pulling petty stunts supposedly because he doesn’t like it that his widowed mother has remarried. Different from the other boys, he’s immediately hazed and asked for his gang affiliation, only he doesn’t have one. Tough boy Henry stands up for him, roping in his other friend Skinny (John Ching Tung) to take on the cell’s Mr. Big after which the boys become firm friends as they study together to sit their A Levels while inside. Wayne wasn’t planning to take his exams as a way of getting back to his mother, but Henry convinces him that education is the one way to show the world who’s boss. The boys come top in their class, Wayne gets out and decides to go the UK to study law, while Henry serves out the remainder of his sentence in an adult prison, sentenced to four years for manslaughter after accidentally killing a triad member during a fight over protection money at his family’s kiosk.
Despite the differences in the scope of their possibilities, Henry and Wayne remain good friends, but once Henry gets out of prison he’s nothing much to look forward to. His hopes of attending a university are dashed by his defeatist father who thinks education is pointless and blames him for the failure of their business, while he struggles to find steady employment as a man with a criminal record. Eventually he decides to work as a mechanic by day and a cram school teacher by night with the aim of saving enough to apply for uni at later date so he can marry his longstanding girlfriend, Winnie (Gigi Lai Chi). Skinny, meanwhile, gets out of jail and heads straight back to the triads, trying to convince Henry he should join too. Henry doesn’t want to, but faces constant harassment from Brother Charlie (William Ho Ka-Kui), the boss of the man he killed in the fight. When his little brother is badly burned in a triad attack, he decides his only option is to become one himself to earn the protection of Boss Sean (Leung Gam-San) who mediates an uneasy truce with the psychopathic Charlie.
When Wayne returns from the UK after graduating law school, Henry is married and a father-to-be living in a swanky apartment having risen in the triad ranks, but he’s also a hotheaded opium addict still sparring with the very present Charlie. “I’m a bad egg! I deserve it!” Henry wails on being confronted by Wayne who points out that it was he who was always encouraging him to study so that no one would ever look down on him. Henry thinks he’s not good enough to be Wayne’s friend and fully expects to be abandoned, but after some strong words of defence from Winnie, Wayne comes around, resolving to help get his friend off the stuff. The problem is the sense of futility which has already set in. Henry has become what everyone expected him to be, a thuggish triad, because they convinced him he could become nothing else.
Winnie berates Henry for keeping his sorrows to himself, remaining sullen and resentful at his inability to escape the triad world for an honest life of safety with his new family, though he once told Wayne that he should “speak up if you feel unhappy”. Despite everything the intense friendship between the two men endures. Cheng adds to the faintly homoerotic tone by shooting his early prison scenes with a lingering romantic gaze, while Wayne seems to pine for his broody friend, affirming that “no matter what you are, you are my buddy”. A caged dragon, Henry’s vengeance is swift and brutal but he retains his nobility even in the depths of his despair, eventually taking refuge in an unconditional friendship which transcends the forces which imprison him.