Frequently hailed as one of the finest actors of his generation, Sean Penn earned multiple Academy Award nominations for his visceral intensity onscreen and proved a powerful filmmaking talent at the helm of his own moody, character-driven dramas – all despite a near mythic persona as the ultimate Hollywood outsider. He owed his early reputation as a fighter to violent run-ins with unwelcome paparazzi, but it was soon apparent that the tenacious idealist was equally prepared to stand his ground on what kinds of stories he wanted to tell and what kind of life he wanted to lead. While his breakout included a beloved teen comedy and a marriage to the top-selling pop singer of the day, Penn quickly established himself as a serious, committed artist whose fierce intellectual integrity meant he spent more time with poets than on red carpets. Penn’s political outspokenness – including taking out an ad in national newspapers calling for the impeachment of President George W. Bush – and his refusal to play the “Hollywood game” by making only the rarest of public appearances to promote his projects, left him with an unshakable reputation as hostile, arrogant and egotistical. Despite these formed opinions, no one could deny that Penn’s work was consistently of the highest caliber, making him a kind of modern-day Marlon Brando who was dependably spectacular in every project he took on.