Oscars: Every Best Picture Winner Ever Ranked From Worst To Best

By Jack Pooley / March 6, 2018

23. Midnight Cowboy (1969)

The first ever gay-themed Best Picture winner, Midnight Cowboy broke new Oscar ground with its frank, sobering depiction of two hustlers trying to eke out a living in New York City by any means necessary.

The film has its rough patches but has generally aged better than most Best Picture winners of the same decade, arriving amid America's counter-cultural upheaval and benefiting hugely from Jon Voight and Dustin Hoffman's wonderful central performances.

As a meditation on masculinity and the American Dream, Midnight Cowboy was a heartfelt provocation back in 1969, and remains almost as affecting today.