The Gentle Friction of St. Mary's
Released as a sequel to Going My Way, this film actually managed to outshine its predecessor in the cultural memory, mostly thanks to the chemistry between its leads. Bing Crosby returns as Father Chuck O'Malley, the easygoing priest with a song for every occasion, but the real heart of the film is Ingrid Bergman as Sister Benedict.
What makes the movie interesting for a modern parent isn't just the 'wholesomeness'—it's the pedagogical debate at the center. O'Malley is the progressive, 'let the kids be kids' type, while Benedict is the disciplinarian who believes in building character through rigor. Watching them navigate these differences without it turning into a toxic rivalry is actually a great lesson in workplace (or community) dynamics.
"I'm not going to have you making a softie out of him. He's got to learn to take it!"
The famous boxing scene, where Sister Benedict dons gloves to teach a bullied student how to fight, remains the film's standout moment. It subverts the 'meek nun' trope and shows a woman of faith who is practical, tough, and deeply invested in her students' survival in the real world.
That said, the movie is very much a product of 1945. There is a subplot involving a student's mother that feels a bit dated in its moralizing, and the ending is a classic Hollywood tear-jerker that might feel manipulative to cynical modern eyes. If you're going to watch it, do it on a rainy afternoon when nobody is in a rush.