Dick Tracy - 35MM

Amidst the triumph of “Vogue” and The Blond Ambition Tour, Dick Tracy was released and features the apex role of Madonna’s cinematic career. Platinum highlights atop the curve of a midnight-black silhouette: Madonna’s shape is pasted perfectly into the vibrant hues and sharp angles of this 1990 noir blockbuster, Beatty’s gangster marriage of Robert Siodmak, Saturday morning serials, and IB Technicolor. Bad-girl-who-wants-to-be-good Breathless Mahoney sashays to showstoppers by Stephen Sondheim (including the Academy Award winner “Sooner or Later”) and mirrors Madonna’s highly publicized relationship with Golden-era leading man Beatty. Dick Tracy is her most Warholian moment, blurring the line between the dream world of Movieland and her very public personal affairs.

Video: VOGUE (David Fincher, 1990):

The crème da la crème of Madonna’s entire creative output, five minutes of idol worship at the pop-priestess’s high altar. Her third collaboration with David Fincher resulted in the best music video of all time for the best dance song ever. With Horst-inspired photography and mega-name dropping rap bridge, Madonna exalts herself into the pantheon of Hollywood icons, cementing her legacy forever.