1. Will Smith had a very successful career in the late 80s and early 90s as the second half of rap duo DJ Jazzy Jeff and the Fresh Prince. But in spite of his financial success, Smith did not manage his money well. It's a pretty classic tale, really. New fame, lots of money, no future plans, and lots of fancy toys added up to a lot of overspending. This lack of oversight and fiscal irresponsibility landed him on the brink of bankruptcy. He owed the government back taxes that he had not paid.