In the pivotal scene of the 1989 rom-com Say Anything…, John Cusack’s character, Lloyd, raises a boombox above his head and blasts Peter Gabriel’s “In Your Eyes” into the bedroom window of his forbidden love. The movie may have been lost to history if it did not include this iconic image.

“In Your Eyes” is a peculiar composition, mixing instrumental strings with electric guitars and choruses sung in Wolof, a West African language. It sounds like all the absurdity and cultural upheaval of 1989 in musical form. I was 16 when I watched Say Anything… with my mom, and the boombox scene was electrifying to me. The song was unlike anything I had ever heard before. I couldn’t tell whether it was love or hate–all I knew was that I was obesssesed.

Until that point, I mostly listened to hip-hop and R&B. There was no use in wasting my time with music adored by previous generations, I thought, when contemporary masterpieces like Kanye West’s My Beautiful Dark Twisted Fantasy and Kendrick Lamar’s good kid m.a.a.d city existed.

“In Your Eyes” totally contradicted this belief. My mom sang along as it played in the movie, and I found myself wishing I knew all the lyrics like she did. The song made me determined to find more music that felt similarly new and exciting, even though it was released decades earlier.

I created a playlist on Spotify that night, named it “Say Anything,” and added Gabriel’s song. The playlist soon became my point of entry into a world of music I had never explored.

For months, I religiously added songs to “Say Anything.” The playlist is mostly classic rock from the 1960s through 80s, and it messily jumps between decades and continents, from bands to solo artists. It is home to Pink Floyd’s tortured “Brain Damage” and James Taylor’s quietly grieving “Fire and Rain.” It is full of contradictions and artistic strife: it includes both “What Is Life,” George Harrison’s jubilant love song, and John Lennon’s “How Do You Sleep,” an excoriating criticism of Paul McCartney that features a traitorous guitar solo from Harrison.

Many of the songs that were part of this exploration were ones I had heard before, at family BBQs or on the radio. In listening to these classics on my own, though, I realized how much I was missing in overlooking rock music. I already knew the Eagles’ “Hotel California,” but when I heard it with my headphones in and mind open, I finally appreciated the strange lodgers profiled in the lyrics and the legendary guitar coda that closes out the track. “Hotel California” was soon added to the playlist.

There was no clear logic governing what music was added—admission to the playlist was based simply on my sense of transcendent connection with a song. I listened to Queen’s “Radio Ga Ga” and added it to the playlist because its use of synths and melding of disco and arena rock seemed so new and daring. “I Want to Break Free,” which I listened to around the same time, didn’t make the cut because I found it much less interesting or inspiring. It didn’t make me feel anything, and this was a playlist entirely based on feeling something, even if that feeling was ineffable. I opted to add Springsteen’s “Born to Run” but not “No Surrender” for a similar reason: “Born to Run” gave me goosebumps when I first heard it. That was enough.

The playlist’s messy, free-form nature was a reflection of my unique and often-contradictory musical preferences. It also influenced these preferences—as I played the songs in “Say Anything” over and over again, I realized I liked 70s’ folk rock a lot more than 80s’ disco, and guitar solos a lot more than drum ones.

The more I listened to these songs and refined my taste, the more curious I grew about other types of music. I started making playlists dedicated to other genres—folk, jazz, alternative rock—or other themes, like my favorite covers, best live performances, great samples. Whenever I tired of adding songs to a given playlist, I would create another one. After “Say Anything,” playlists became free-wheeling, open-ended creative projects through which I could discover new music from the ground up.

The blank-canvas quality of “Say Anything” reflects the broader ways people in my generation think about collecting music. Some playlists are perfectly-manicured Pinterest mood boards, while others are curated more naturally, through random or even arbitrary decisions about where songs belong. Playlists have limitless possibility; they are an art form that lacks definition.

This column is meant to dissect how and why we create playlists, and what they mean to us. Why are certain playlists public or private? Why do some people make playlists with their friends or playlists dedicated to every month? “Say Anything” was the first playlist that I had an emotional stake in—it was my entrance into the lifelong project of discovering my own music taste.

The final song in the playlist, “Domino” by Van Morrison, was added on December 2nd, 2020, only a few months after my project had been started. “Say Anything” is stuck in time, a collection of the very first experiences I had with artists who have become some of my all-time favorites, artists whose discographies I now know like the back of my hand.

It’s funny to think that a random song from a movie inspired me to explore these new music genres. The unexpected impact of “In Your Eyes” reflects how finicky music taste can be, how easily it’s swayed by serendipitous discoveries.

One of my most lucky musical moments was that “In Your Eyes” played from Cusack’s boombox at all. The movie’s director initially wanted to use “Question of Life,” a deep cut by the punk band Fishbone, for the movie’s iconic scene. “Question of Life” is grating, muddled, and exhausting—the opposite of romantic.

I always wonder what the version of “Say Anything” that was inspired by Fishbone might have looked like. Maybe it wouldn’t have existed at all, or maybe it would have revealed an entirely different side of my music taste, one that I am still waiting to discover.