Jared Pillows
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Description: One of the enduring images of 80s high school comedy dramas is from 1989's Say Anything with a young John Cusack serenading his would-be girlfriend by playing Peter Gabriel's "In Your Eyes" on his boombox. Lloyd Dobler is one of a select number of trenchcoat wearing film and TV characters along with everyone's favourite Supernatural angel, Castiel, who features here in Lloyd's iconic pose.
