4. Dirty Harry
Not only did Eastwood's portrayal of San Francisco cop Harry Callahan in Dirty Harry make him one of Hollywood's top leading men, he also created a role that spawned 4 sequels, and one of the most memorable movie quotes of all time. In this 1971 blockbuster, Eastwood is firing from all cylinders as he is sent on the trail of a crazed serial killer named Scorpio, only to lose him through the cracks of the justice system. Eastwood takes the law into his own hands and the results are astounding. Eastwood plays "Dirty" Harry with such commanding stoicism, and never makes his larger than life character a joke or a cliche in an otherwise pulpy cop film. While toting a massive .44 Magnum for good measure Eastwood instills fear into his prey, just by pointing it his way and asking him if he "feels lucky". Clint was certainly lucky for this once in a lifetime role, and he does not disappoint.