These posts are about the songs that fell just short of crossing the key line of chart success, entering the Billboard Top 40. Every song featured in this series peaked at number 41.

Cameron Crowe was trying to crack a problematic scene in his new screenplay about a romance between two teenagers during the summer after their high school graduation. The girl had broken up with the boy, and he was reeling from it. Crowe wanted a dramatic gesture for the boy, something that would properly and succinctly show how he was feeling and how desperate he was to win back the girl. A scribe for music magazines since he himself was a teenager, Crowe knew better than most how pop music could easily become a stand-in for emotional expression for certain young fellas, so it’s no surprise that he landed on the idea of the boy literally using a meaningful song to call out to the girl. As he was writing, there was a new hit song marching up the charts that Crowe was particularly fond of, so he wrote it right into the script. The boy stands outside of the home of the girl, holding a boombox over his head. From the speakers plays the Top 10 single Crowe liked: Billy Idol’s “To Be a Lover.”

That script became the film Say Anything, Crowe’s feature directorial debut. By the time he shot the scene in question, with John Cusack playing Lloyd Dobler (the boy) and Ione Skye as Diane Court (the girl), Crowe had soured on “To Be a Lover.” On set, the Fishbone song “Turn the Other Way” blurted from the boombox, but Crowe knew that cut wasn’t right either. As he worked on the the edit, every song they placed into the scene was a failure. Then Crowe found the answer the way all moony, music-fan dudes land on upon elusive truths: He listened to a mix tape.

“I was driving to work and on my way to the editing room, and I just found this tape again the other day, there was a tape that I had in the car that was the mix from our wedding and it was called ‘The Legendary “I Do” Tape,’ and I put it on and I was just listening to it on the way,” Crowe told Entertainment Weekly on the occasion of the film’s twentieth anniversary. “I’m not that much of a wimp, but for some reason I just felt like listening to my wedding tape. And ‘In Your Eyes’ comes on. And I got this chill because all the words linked up to what we’d filmed and what we were struggling to find a score to or a song.”

Crowe was now determined. Peter Gabriel’s “In Your Eyes,” from the hit album So, was the only song that would do. The new problem was that Gabriel was famously reluctant to license his songs for films or other use apart from his records. Crowe was warned to expect a rejection, and that’s exactly what he got. The studio had sent a work-print copy of Say Anything to Gabriel, and Crowe waited anxiously for word. Finally, the two talked by phone and Gabriel turned Crowe down. When Crowe asked why, Gabriel said the film’s drug overdose scene was too rough for his taste. After some back and forth, Crowe figured out that Gabriel had actually watched a different film sent by the studio: Wired, director Larry Peerce’s adaptation of Bob Woodward’s controversial John Belushi biography. After Gabriel actually saw Say Anything, he agreed “In Your Eyes” could be used in the scene. Reportedly, the endorsement of Rosanna Arquette, who inspired the song in first place, helped seal the decision.

Although Say Anything became a beloved movie for Generation X, it wasn’t a box office success upon its release. That boombox scene, though, was immediately iconic, and “In Your Eyes” was released as a single from the Say Anything soundtrack. Really, the song was rereleased as a single. Three years earlier, “In Your Eyes” was the follow-up to Gabriel’s chart-topping “Sledgehammer.” At that time, it climbed to #26 on the Billboard chart, becoming Gabriel’s third Top 40 hit. It didn’t fare as well as a rerelease, peaking at #41.

Other entries in this series can be found by clicking on the “Top 40 Smash Near Misses” tag.