John Cusack delivers one of the best performances of his career as Lloyd Dobler – so believable, so appealing, and so earnest. He thinks and talks like a real person. He fidgets and paces nervously when he calls Diane up for a date. He’s level-headed and uniquely insightful and perceptive. He says things like, “I’m looking for a dare to be great situation.” He doesn’t spout clichés. He wears his heart on his sleeve. He knows himself and he doesn’t fake anything or ever pretend to be someone he’s not. The film’s movie poster reads: “To know Lloyd Dobler is to love him,” and it’s true. Lloyd is, quite frankly, one of the best boyfriends in film and no scene proves it more than the iconic boom box serenade.
It’s the scene in the movie that gets the most attention because it’s one of the most memorable declarations of love in film. When Diane breaks up with Lloyd out of a combined fear of commitment and her father’s disapproval, he’s absolutely heartbroken. Lloyd does everything to win Diane back, and in the grandest, most romantic of gestures, he stands outside her bedroom window holding a boom box over his head as “In Your Eyes” by Peter Gabriel plays. It’s the song that played on the radio after their first time in Lloyd’s car. The look of resolute determination on Lloyd’s face as he hoists the boom box higher overhead, feet planted firmly on that spot outside Diane’s window, defiantly pleading with her to take him back, has become one of the most enduring and iconic images in 80s film.