Answer
Jon Cryer played the role of Duckie in the 1986 John Hughes film Pretty in Pink. Duckie was the best friend of the protagonist, Andie, who was played by Molly Ringwald. The film follows Andie as she navigates the social scene of her high school, where she is torn between her friendship with Duckie and her attraction to the popular boy, Blane, who is played by Andrew McCarthy.