Every Best Actor Oscar Movie Winner Of The 21st Century Ranked
13. Sean Penn - Milk (2008)
Who should have won: Mickey Rourke - The Wrestler.
Throughout his career, Sean Penn has shined as the tough guy, always at his best when bringing angry, explosive anti-heroes and lost souls to life. His portrayal of late gay rights activist Harvey Milk beautifully subverts these expectations.
Tender and thoughtful, Penn's performance in this oft-forgotten biopic is haunting and gentle, as he brings Milk to life as a lovable fighter with heaps of heart and uncompromising inner strength. Penn has never been so vulnerable and inspiring, and he wears Milk's quiet anger and passion like unbreakable armour.
He maybe didn't deserve to best Mickey Rourke's soul-crushing performance in The Wrestler, but watch Milk again and you'll find it tough to hate the Academy's decision. Penn grips you in a warm embrace, then breaks your heart without flaw.