John Cusack reveals he didn’t know how to approach iconic boombox scene in "Say Anything"

“Guys have pride, right?” he quipped, underscoring how uncertain he felt about the gesture at first

John Cusack is opening up about one of cinema’s most enduring romantic moments, the boombox scene from the 1989 classic Say Anything, and reveals that its emotional power wasn’t immediately clear to him.

More than three decades after the film’s release, the 59‑year‑old actor said he initially “didn’t know how to do it” because he worried that standing outside Diane Court’s window with a boombox might come off as the character whining rather than expressing genuine feeling.

“Guys have pride, right?” he quipped during a recent screening of the movie in New York City, underscoring how uncertain he felt about the gesture at first.

Cusack said he eventually found the right emotional approach by shifting his understanding of what Lloyd Dobler was communicating.

Rather than portraying the character as pleading, he chose to infuse the moment with a sense of defiance and belief, turning what could have been a desperate plea into a bold declaration of conviction. This change helped transform the scene into the iconic image beloved by fans and widely referenced in popular culture.

The actor also shared that his involvement in shaping Lloyd’s voice went beyond just that scene. Cusack negotiated with director Cameron Crowe to adjust the script so that Lloyd would feel more authentic — not just romantic, but intentionally optimistic.

He wanted the character to be seen as choosing hope, a nuance he felt made Lloyd “sort of heroic” and more emotionally grounded.

Today, the boombox moment, set to Peter Gabriel’s In Your Eyes, remains one of the most memorable sequences in film history, a testament both to its emotional resonance and to Cusack’s thoughtful performance choices.