Youth of Fortune (1916)

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Seventeen-year-old Willie O'Donovan (Carter DeHaven) has been sent to boarding school because his parents have other things to worry about, including the probability that they are headed for divorce court. Willie spends his time there coming up with wild pranks and romancing a milkmaid (Flora Parker, DeHaven's real-life wife). Willie's grandfather, who for some reason holds the boy in high regard, dies and leaves him his vast fortune, which shall be controlled by a guardian -- the guardian being whoever Willie is living with on his 18th birthday. Both parents want to be that guardian, so they each send detectives out to kidnap the boy. Willie, however, sees through this and has no problem tricking the inept men his mother and father have hired. In the end, he marries his milkmaid sweetheart, who becomes the guardian, as she's the one who is living with him on his 18th birthday.