I haven't seen most of Jackie's films, but my favorite is Ji ji (Miracles). In his IMDB trivia, it says that this is Jackie's favorite film.
Ji ji is a Cantonese version of a Capra film. The late Anita Mui gave a classic performance and sang a great version of "Rose Rose I love you." Jackie used this Chinese hit from that era the theme song and the theme of the movie. The pacing was just right and some of the best character actors in HK were in it. There is some fighting and stunt work, but this is Jackie's serious film, albeit a comedy.
Ji ji is about a poor schnook who stumbles into a position as a crime boss. However, he is a gang boss who uses his resources to pull off a caper to help a poor flower lady.
Jackie's parents had a tough life because of the turmoil of 20th century China. His father barely survived an execution, worked for the KMT, was shot in an assassination attempt as the head of an intelligence unit, and belonged to a gang.
Jackie's mom was an opium smuggler and a gambler.
The threads of Jackie's life are bound up in Miracles.
Someone mentioned City Hunter. I give it honorable mention because the unbelievably breathtaking Joey Wong is in City Hunter.
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