Midnight Cowboy (1969)

Ogle Angelina Jolie’s daddy – Jon Voight – as he plays a naïve trick decked out as the ultimate urban cowboy. The movie captures the seedy side of Times Square, and features some interesting cameos – like underground New York legend and Warhol friend Sylvia Miles. It also comes with a brilliant soundtrack courtesy of A.M. radio superstar Harry Nilsson.