A$AP Rocky
As a teenager, A$AP Rocky lived in homeless shelters with his mother and sister, resorting to illegal activities to support his family.
In 2004, he was arrested and spent two weeks in prison, where he met fellow rapper Cassanova, sparking both their careers. Today, A$AP Rocky has an estimated net worth of $10 million and is in a relationship with billionaire Rihanna, with whom he shares a child.