Best Actor Oscar-Winners Since 2000, Ranked Worst to Best

From French comics to Method-acting chameleons, our updated list on the gentleman who have taken home the 21st-century gold

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Sean Penn, 'Milk'
Kevin Winter/Winter11/17

11. Sean Penn, 'Milk'

If Sean Penn's Oscar win for Mystic River demonstrated his wiry ferocity, his turn as slain gay-rights activist Harvey Milk illustrated his sweetness and compassion. In a career personified by playing tough guys (both onscreen and off-), Penn displayed a rare gentleness here, which doesn't mean that he wasn't any less steely in this role. Indeed, Milk is a sort of coming-of-age film that follows its hero on a path to finding himself and, at the same time, pushing others to accept homosexuals into their communities. Penn has perhaps never been more lovable, a quality that's rarely been associated with this actor. But look how well he wears it.

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