It is so hard to pick a favorite. If I must, I will go with the first Harry role. Harry Palmer of The Ipcress File. Caine proved he could lead a film. Spy movies and TV were quite the in thing at the time but Michael Caine's Harry Palmer was different. Caine walked a fine line with a character that was nerdy/sexy, boring/interesting. He was the anti-Bond and deftly showcased a quirky, understated cool.