Director: Richard Press

If you aren't familiar with Bill Cunningham, this documentary is a great start. Press, who reportedly spent eight years convincing Cunningham to be filmed, tells the story of the New York Times photographer and his importance to streetstyle photography—Anna Wintour will often only stop and have her photo taken by Cunningham. While the film is about his work, Cunningham reveals quite a bit about his personal life as well. He allows Press inside his tiny Carnegie Hall studio, discusses his stint as a hat designer, and more. We won't spoil everything for you, but one of the most interesting things about this man is how old school he is about everything, despite his popularity. 

Buy the DVD now at Best Buy.