Here I attached a great song by Tony Bennett titled "Rags to Riches". He is singing that he will be a king in his heart once he has this special girl to whom he is singing. It gives a different view on this common phrase. Riches is not in the wealth that one has, but the love and happiness that they have.
The one rags to riches story I can think of is an old television show, "The Beverley Hillbillies". It is a story of a poor family that found oil on their land, and moved to Beverley Hills with their new fortune. I still watch the show when I find it on television. It always makes me laugh, as it is a great rag to riches story which pokes fun at the idea that the people who go to riches adjust automatically. In this case, they do not. They greatly enjoy their new money, but do not fit into their new society, which makes the show so comical.
The other day my mom was actually telling me about a show she saw on T.V. about lottery winners. The one man was homeless, living on the street, when he won the lottery. One would expect him to go buy a house, but rather, he lives in a motel. It was such a big difference and change, that he doesn't even know how to spend the money. It can be a great change to win the lottery, or strike oil, but also difficult.