6. Clint Eastwood - From Grizzled Actor To Oscar-Winning Director
I suppose it's only natural that you're going to learn a thing or two about directing if you spend so long hanging around Sergio Leone, but Clint Eastwood's transition from revered Western actor to acclaimed director was nothing if not unexpected. Having carved out worldwide fame for himself as the star of Leone's Dollars Trilogy, Eastwood didn't waste much time at all in turning to directing, pumping out a string of acclaimed works including Play Misty for Me, High Plains Drifter, The Outlaw Josey Wales, Pale Rider, Heartbreak Ridge, and only then did things get
really good... 1992's Unforgiven saw Eastwood's first Best Director Oscar win, and 2004's Million Dollar Baby secured him his second, while he racked up nominations in 2004 for Mystic River and 2007 for Letters from Iwo Jima as well. Few could have possibly foreseen that such an iconic actor would become an even better director than he is a performer.