YMMV / Shanghai Grand

• Complete Monster: Madam Yiu is a high-ranking enforcer of the Triads who willingly sold out her country in exchange for a position of power in the Shanghai criminal underworld. Introduced killing a helpless captive by chewing out his throat, causing him to die slowly and painfully, Madam Yiu later forcefully interrogates the protagonist Hui Man-keung while having him hung by his neck on a wire, in order to maximize his suffering, which she thoroughly enjoys the entire time. When Man-keung managed to escape, in order to intimidate him, Madam Yiu then machine guns twenty caged prisoners while bearing a sadistic smile on her face, before ordering their bodies to be dumped in the waters outside Shanghai. Stopping at nothing to hunt down Man-keung, she willingly ordered her mooks to shoot up a city building, and later lures Man-keung and his best friend Ding-lik into a trap, where she had Ding-lik captured alive, Chained to a Bed, and subjects the man to torture by slitting his chest open with a stiletto, and tries to feed him to a boa constrictor.
• Tearjerker: Well, this being a gangster movie, its a given, but the idea of two best friends who went through thick and thin together before being destined to kill each other definitely counts as sad.