"Pretty in Pink," 1986 The Role: Molly Ringwald as Andie Walsh Her Prom Song: "If You Leave" by OMD Why We Love It: Determined to show her high school's rich snobs that they didn't break her, Andie... more 

"Pretty in Pink," 1986 The Role: Molly Ringwald as Andie Walsh Her Prom Song: "If You Leave" by OMD Why We Love It: Determined to show her high school's rich snobs that they didn't break her, Andie creates an 80s-tastic prom dress from a hand-me-down. End result: She makes them all look like jerks -- and she gets the guy. 100 Best Dresses of the Decade Paramount/Courtesy Everett Collection - 1986 less