Sean Penn, “Milk”(2008)
“How did he do it?” queried Robert DeNiro at the Academy Awards. “How for so many years did Sean Penn get roles playing straight men?” That’s how good Sean Penn was in the role of martyred gay activist Harvey Milk. In Gus Van Sant’s masterpiece, “Milk,” Sean Penn drops his usual craggly, Marlboro-slicked machismo to give one of his most compelling and sensitive performances to date. Penn brought an undeniable (and necessary) magnetism to the iconic politician whose quixotic journey took him from Castro camera shop owner to the first openly gay member of the San Francisco Board of Supervisors.