Clint Eastwood — $370 million
Most financially successful movies (as an actor and/or director): Dirty Harry, The Good, the Bad and the Ugly, A Fistful of Dollars, Million Dollar Baby, Gran Torino, Sully.
He is the idol of our grandmothers, our mothers, and even us. It has been almost half a century since this brilliant cowboy took part in westerns, action movies, and dramas. He also shoots movies. They are not always financially successful, but they won him 4 Oscars.