Boombox Serenade (Say Anything…)
Welcome to The Grand Gesture, my new feature that will be taking a deeper look at iconic rom-com moments in film history. I’ve been wanting to expand what I do here at The Rom Com Catalog, and while I was compiling my list of my Top Ten Favorite Rom-Com Moments, I thought it would be fun to dive into the scenes that we remember most from these movies and how they impacted the romantic relationships. “That scene is like Romeo under the trellis.” – Cameron Crowe
THE GRAND GESTURE
One of my favorite scenes in rom-com history also happens to be one of the most iconic. When you think of Cameron Crowe’s 1989 romantic dramedy Say Anythingā¦, it’s hard not to immediately imagine the heartbroken but defiant Lloyd Dobler, standing outside at dusk, boombox raised as Peter Gabriel’s In Your Eyes plays down the hillside and into the open window of Diane Court. It’s even harder to imagine that this scene might have played out differently, or worse, not at all.

When Crowe initially wrote the scene, he included a different song – To Be A Lover by Billy Idol. But when shooting the scene, the song didn’t work. According to Crowe, they attempted several songs, but nothing was quite hitting the emotional tone that the scene needed. And then, one day, Crowe was driving and listening to a cassette that contained various songs from his wedding to Nancy Wilson. When In Your Eyes came on, Crowe knew this was it – the song.
But getting Peter Gabriel to approve the use of the song was going to be a difficult task. The studio wasn’t terribly thrilled with an early screening of the movie and wasn’t willing to go to bat for Crowe in obtaining the song. But Gabriel’s girlfriend at the time, Rosanna Arquette (whom it’s said In Your Eyes was written for), put in a good word for Crowe, and Gabriel was sent a copy of the movie. When Crowe and Gabriel finally connected over the telephone, Gabriel said no. When Crowe asked why Gabriel said it didn’t seem to fit the overdose sceneā¦Peter Gabriel had confused the song request for a John Belushi film (Wired). When he finally watched Say Anythingā¦ he agreed to let Crowe use the song.

With the perfect song in place, Crowe then had to deal with his two young actors and their discomfort and doubts over the scene. Ione Skye, who was seventeen at the time, wasn’t fond of the scene at the time of filming. She was nervous and disliked the top she had to wear and felt the whole scene was silly. Cusack wasn’t sure the scene would work either, thinking that Lloyd was kowtowing in the scene, and his defiance in the scene stemmed from Cusack’s own doubt about the scene. But rather than hinder the emotion of the scene, Crowe feels like Cusack’s performance only made the scene better.
“He made it work. The way he performs it, itās just blatantly defying you to consider it cheesy. That’s why heās so heroic in that moment. Heās still doubting whether the boom box scene is going to work at all. Heās kind of fighting for the scene.”

The actual boombox scene was filmed in North Hollywood Park, across the street from the 7-Eleven featured earlier in the movie, during Diane and Lloyd’s first date. And yes, the actors filmed separately. The final result? It is a gorgeously shot scene where the two teenagers’ heartbreak, yearning, and regret are reflected perfectly in the song and the emotion on their faces. It’s not the moment that sparks a reconciliation, but it shows Lloyd’s devotion to Diane and his unwillingness to let her drive him away.
Lloyd’s boombox serenade has taken its rightful place in pop culture, being parodied and imitated in shows like The Goldbergs and Modern Family, as well as films like Deadpool. SNL even did a boombox sketch with Joseph Gordon Levitt as Lloyd – which, sadly, I could not find online. In any case, the scene is undoubtedly a quintessential moment in coming-of-age/teen romances, not only in the 80s but of all time.
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