High Sierra form 1941 with Humphrey Bogart, Ida Lupino, Henry Travers and Joan Leslie
There's a lot of moral ambiguity going on beneath the code-approved wrapping of this gangster picture cum film noir where you end up kinda rooting for the wrong people at times.
Bogart, serving a life sentence, is sprung from jail by a governor's pardon obtained by a bribe paid by a gang leader who gets Bogie freed so that he can mastermind a heist for him. Pause on that corruption at a high level for a moment; a corruption that is not later "fixed" by the Motion Picture Production Code. It is never exposed and the governor suffers no consequences.
Bogie, now freed and on his way to the heist job on the west coast, befriends a poor family whose one daughter, Joan Leslie, has a club foot. His kindness to the family and girl reveals that Bogie has a mixed-up morality that can be cold and ruthless at times, but also kind and caring.
Once out west, Bogart connects with the new gang - amateurs that he tries to mold into professionals while he meets hanger-on-girl Ida Lupino, whose horrible family life has led her to become, essentially, a gangster groupie. Here again, we see Bogie the antihero as a caring man who shows kindness to Lupino. And Lupino, like a beaten dog, responds with love and devotion to the modest scraps of decency Bogie throws her way.
But Bogie's real affections are reserved for club-footed Leslie who seems to represent for Bogart the innocence of his youth and the respectability society will no longer offer him. With the movie's two paths - a crime caper and a love triangle - set, we shift to the jewelry heist part of the story, which goes horribly wrong as we see the ruthless side of Bogie when he shoots innocent people who get in the way.
From here, it's all a painful unravel of the few hopes for a normal life Bogie and Lupino (she sticks to him like glue) have. After paying for a surgery to fix Leslie's foot, Bogart asks her to marry him, but she rejects him, at first nicely, and then, as he pushes, not so nicely.
With that dream crushed, the law closing in and Lupino still around, Bogart ships Lupino, who is kinda sorta not guilty (other than that she knew the heist was being planned), ahead to Vegas so that he can try to escape the law and get the money from the stolen jewels on his own.
But it's the 1940s and even antiheroes have to pay for their sins, so (spoiler alert) in a well-filmed, tense final scene, Bogie, with a rifle and plenty of ammo, attempts to hold off the police in the Sierra Mountains. During the standoff, Lupino appears pleading for Bogie's life. But in a final twist of irony, as Bogie goes to pick up his and Lupino's dog - who Lupino brought with her and who has run up to Bogie's redoubt - Bogie exposes himself enough to be shot.
The man is a ruthless killer; a hardened criminal foreshadowing a Tarantino character by decades as he sees crime and even murder as just part of his job. But he can also be kind, wistful and compassionate, and darn it, half the time you are rooting for him. Kudos to writers John Huston and W.R. Burnett and director Raoul Walsh for creating a morally complex character and story tucked inside the tightly circumscribed world of the Motion Picture Production Code.