27. Brokeback Mountain
In a time before gay marriage rulings and only seven years after the brutal murder of gay man Matthew Shepard, Brokeback Mountain was highly controversial for its depiction of a love affair between two stereotypically masculine ranch hands. The beautifully shot and directed film lost to the controversial race-relations film Crash. Many critics at the time blamed homophobia for keeping Brokeback Mountain out of the winner’s slot, as Crash was widely regarded as a much weaker film.