Actor. Director. Writer. Producer. Author. Songwriter. Playwright. In 2011, Forbes said Tyler Perry was the highest paid man in entertainment (he had earned $130 million in the previous year alone). And while he isn't afraid to delve into the dramatic side of life, Perry's greatest success will always be associated with Madea, a thuggish old lady played by Perry himself. Sort of like a real-life version of Tootsie.