Little Men (1998)

1871 New England. Two-week orphaned preteen Nat Blake, in his new circumstance, has been living on the streets of Boston with his more streetwise friend, fourteen year old Dan, who looks after Nat and who survives by his cunning and by stealing. Due to an event of living on the streets, Nat gets a benefactor in the form of John Brooke who pays for his schooling at Plumfield, a boys' boarding school in the country owned and operated by John's sister-in-law and her husband, Jo and Fritz Bhaer. Although each being different in the way they exact their discipline, both the Bhaers believe that treating the boys with compassion and treating them as boys will result in them being better people than if they were strict disciplinarians. Nat goes through some adjustment of needing to lie to survive on the street to life at Plumfield, but ultimately finds that that different life is one to which he truly wants and that the changes he has to make do make him a better person. Nat's stay at Plumfield is further affected by two subsequent arrivals, one being Dan who has no benefactor to pay his way at the school (which is facing financial problems), but it where he says he wants to be despite he treating his stay there the exact same as he is when he is on the street: by his own rules, and not the Bhaers or anyone else's.