The cartoon boy might be bare foot for a variety of reasons. It could be part of the story's setting, like a beach or a grassy field. Or perhaps it's to show his carefree and wild nature. Sometimes, it's just an artistic choice to make him stand out.
Often, in such parables, the crossroads can signify a moment of moral or ethical dilemma for the rich man. It could be a place where he has to decide between selfishness and altruism, wealth and integrity.
In a cartoon, cats and pencils might be brought together in a creative way. Maybe the cat is playing with a pencil or using it as a toy, but it's not a common or obvious link.