Rather than simply using reproductions of the movies' posters and promotional art as stand-ins for each film, we decided to use minimalist icons representing notable images, props, or costumes from each film. For example, we used Scarlett O'Hara's red hoop skirt from Gone with the Wind (1939), Poor Yorick's Skull from Hamlet (1948), Jon Voight's Stetson jacket from Midnight Cowboy (1969), the silver dog tags from Platoon (1986), and the wind-blown plastic bag from American Beauty (1999). Our team also decided that black and white films—including nearly all of the winners until 1955, and Schindler's List (1993) and The Artist (2011) later on—should be represented with grayscale icons.
Our strategist and art director worked closely with the illustrator to make sure that each icon accurately represented the film in question. While we had collectively seen most of the recent entries on the list, there were certainly a lot of older and less well-known entries with which we were unfamiliar. This meant we needed to go back and watch said films, or at minimum research them thoroughly enough to identify an iconic scene or prop.
By using less on-the-nose imagery for each icon and hiding the film title at the bottom of the graphic, we were able to entice readers (and especially film buffs) to "guess" which film particular icons represented.