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Family-Unfriendly Aesop: Owl Jolson's father only approves of his son's singing when he's about to benefit financially from it. He only encourages his son to sing the way he likes to ensure he takes home the prize. Try not to think about how he would've reacted if his encouragement came too late and the kid still lost the contest.
There's also the possibility that Owl Jolson's father was encouraging it anyway, regardless of whether Owl Jolson won the contest or not, which would avoid this problem entirely.