John Cusack thinks one of his most famous romantic gestures could land differently if Say Anything… were made today. Lloyd Dobler’s attempt to win back Diane Court, he suggested, might get the character called a stalker.
Speaking with Josh Horowitz on the Sept. 28 episode of Happy Sad Confused, Cusack imagined viewers objecting that Diane had already established boundaries. “You’re stalking her,” he said, describing that hypothetical reaction, according to Entertainment Weekly.
In the 1989 film, Lloyd stands outside Diane’s home after their breakup, holding a boombox above his head while Peter Gabriel’s “In Your Eyes” plays. Ione Skye’s character listens from inside.
Cusack brought up Lloyd during a broader discussion about moral ambiguity in movies and the freedom to follow characters whose behavior audiences do not always admire.
Cusack Questions the Demand for Likable Movie Characters
The discussion began with Being John Malkovich, as Horowitz and Cusack considered the appeal of an unlikable protagonist. Cusack described the interest in watching people who are stuck in unhealthy relationships and make uncomfortable choices.
He also pointed to Rob Gordon, his character in High Fidelity. Rob’s selfishness and mistakes are part of what the film explores, alongside his capacity for reflection and change.
During the interview, Cusack argued that a person can behave foolishly in one situation and thoughtfully in another. He said he finds it interesting when a performance leaves him feeling repelled by someone while still wanting to understand them.
Cusack Resisted the Boombox Pose During Filming
Director Cameron Crowe recalled a different objection to the scene in a September 2025 interview with The New York Times: Cusack thought the pose made Lloyd look too submissive.
They tried a version with the stereo resting on a car hood, which Cusack felt suited the character better. Crowe recalled cinematographer László Kovács quietly telling him that there was no film in the camera during that attempt.
The familiar shot came on the final day of filming. With daylight fading, Kovács found a location across the street, and Cusack agreed to raise the stereo. Crowe said the actor’s lingering irritation gave the moment exactly the emotion it needed.
Cusack offered his own explanation at a Nov. 30, 2025, screening at New York’s Kings Theatre. As People reported, he had struggled to approach the scene without making Lloyd seem as though he was pleading. He eventually played it with defiance, drawing on Lloyd’s suspicion that something else was behind Diane’s decision.
He Worked With Crowe to Give Lloyd His Own Voice
Cusack told Horowitz that his concerns about Lloyd extended to the dialogue. He wanted the character to sound like a young person with his own opinions, including ideas about work, money and what kind of life he wanted.
He said he accepted the role on the condition that he could work through the material with Crowe. His vision included a teenager who might wear a Clash T-shirt and question the expectations placed on him.
That collaboration helped shape Lloyd’s dinner-table speech about refusing a career built around selling, buying or processing things. Cusack said he developed the opening portion, while Crowe supplied the turn toward Lloyd simply wanting to spend time with Diane.
Cusack also credited Skye and John Mahoney, who played Diane’s father, with bringing weight to the family story. Mahoney had worked with him on Eight Men Out and encouraged him to take the role when he was reluctant to make another film about teenagers.
Skye Had Her Own Answer to the Stalking Question
Skye addressed similar questions in a 2019 interview with Showbiz Cheat Sheet at the film’s 30th-anniversary Tribeca celebration.
She acknowledged that some of the tension comes from wondering whether Lloyd is being protective or taking his pursuit too far. For her, the relationship he and Diane had already developed mattered to how those moments played.
“I mean I think they’d already had enough between them so it wasn’t too stalkery,” she said.