My Life In 35 Songs, Track 1: “One Headlight” by The Wallflowers

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If your life was a movie, what songs would make the soundtrack?

Earlier this year, I found myself trying to answer that question, all because I was looking for a project to get me excited about music writing again. A decade ago, I couldn’t wait to write up reviews of every new album I liked. Now, the thought of going through that process feels exhausting, and maybe meaningless. Does anyone care about album reviews in 2025? And if not, where does that leave those of us who love trying to articulate what it is about a certain piece of music that makes us think, or makes us weep, or gets our hearts racing a little faster?

I came up with the life soundtrack idea almost on a lark. It would be a fun challenge, I told myself, especially if there were limits and rules by which I had to abide. The first rule I gave myself was to theme this project around my forthcoming 35th birthday. In honor of that milestone, I decided, I’d have the space of just 35 songs to tell my life story.

I didn’t know how maddening this game would prove to be – or, ultimately, how emotionally fulfilling. I’m an old veteran when it comes to making lists, but this version of the music list was so much harder than anything else I’d ever attempted. Picking your all-time favorite albums is easy. Picking your favorite songs is harder, but still somewhat intuitive. Trying to boil down your entire life’s journey into what is essentially a two-CD compilation is an exercise guaranteed to result in constant hand-wringing, excessive second-guessing, and endless revising. There are currently 47,145 songs in my iTunes library. How was I supposed to be satisfied picking such a tiny percentage of that?

While making the playlist was tricky, though, the writing project that this whole silly endeavor birthed has done what it was supposed to do by reinvigorating my passion for writing about music. Anyone who has read my work on this website knows that I have always been most interested in the way that music intersects with our lives. Most of my writing for Chorus.fm for the past five or so years has been retrospectives about albums hitting the 10-year or 20-year mark, and all those pieces are as much about my life as they are about the albums themselves. A great song is never just a song; it’s a part of someone’s soul, and the 35 songs I chose for this journey are all a part of mine, for reasons I can’t wait to share.

My initial plan was to post this series on my personal blog, because it felt so…well, personal. In movies, the big needle-drops you remember most tend to be around big, emotional moments: moments of friendship, moments of love, moments of triumph, moments of tragedy. Such was the case, ultimately, with the soundtrack I built for myself, and I wasn’t sure it would make sense to share that anywhere but a personal blog. When I brought up the idea to Jason, though, he loved it, and encouraged me to run the series on Chorus.fm. Now that I think about it, I can’t think of a better place for this project to live than a website that once bore the tagline “Music Mends Broken Hearts.”

So, here’s what’s coming: Starting today, and running until my 35th birthday in November, I’ll be sharing one essay per week about a song that, for one reason or another, mattered profoundly in the course of my life. The essays blend personal memoir with musical commentary and criticism, sometimes leaning more in the former direction, sometimes tilting more in the latter. Each piece comes from a place of deep love for this music, and I’m sure it’s no surprise that many of the songs and artists featured will be shared fascinations of the people in this musical community. So, I hope you’ll take the journey with me – and perhaps share your own life soundtracks along the way. Every one of us has a unique “audiobiography,” and I look forward to talking about them.

Last bit of preamble: As I mentioned above, making a list like this one only shifts from “impossible” to “extremely difficult” if you give yourself rules and limitations. So, here are the rules I set for myself:

• One song per artist, no exceptions.
• The songs I chose could be spaced out throughout my life in whatever distribution made most sense narratively. There was no requirement, in other words, to include one song for every year of my life. Some years get 2-3 songs. Many get zero.
• No excluding songs because I found them slightly embarrassing in retrospect. Too many people are ashamed of their musical roots, but we all have them, and they are a crucial part of a story like the one I wanted to tell here.
• Remember that it’s not just a list of favorite songs! Many of my all-time favorite songs will be featured throughout this series, but there were just as many situations where I was surprised at the songs I found myself selecting for specific artists, or at the albums I wasn’t able to represent.
• Don’t be afraid to adjust the playlist as you go, if something feels off! For this reason – and given the fact that I still have eight months left as a 34-year-old – I will not be sharing the full track list upfront. Instead, I’ll reveal the tracks one by one as I publish each new essay.

OK, I think that’s really it for housekeeping. Without further ado, let’s put the CD in the boombox and cue up track 1…

So long ago I don’t remember when, that’s when they say I lost my only friend…

What was your first favorite song?

Throughout my life, I have loved literally tens of thousands of songs, from all manner of different artists, for so many unique reasons. But if you asked me for a full accounting of the songs that I have, at one time or another, called “my favorite song,” I think I could count them on one hand. “One Headlight,” the big signature smash hit from ‘90s folk-rockers The Wallflowers, was the first song I ever held in such high esteem.

There’s this atmospheric, echoey guitar sound that kicks off “One Headlight,” and it might be my favorite sound in the world. Hearing it as a kid never failed to instill a huge amount of anticipation in me. I was five years old when this song made its way out into the world, and probably six when it began its momentous journey up the charts. Back then, I didn’t have the luxury of cueing up my favorite song at a moment’s notice, so hearing “One Headlight” in any situation – on the radio; on MTV; in my brother’s room when he played his CD copy of Bringing Down the Horse¸ the superb 1996 LP from which the song hails – was nothing short of thrilling.

I loved “One Headlight” so much that I eventually had my brother make me a bootleg cassette copy of Bringing Down the Horse, and I wore that thing out playing and rewinding “One Headlight” over and over and over again. I liked a lot of the other songs on the album, too – especially “The Difference,” a propulsive summer night banger in the track 5 slot – but “One Headlight” was the one for me. I built a makeshift drum set in my room out of frisbees and aluminum popcorn tins, just so I could play along with the song’s steady beat. When summer came, I’d prop my tape player up in my bedroom’s second-floor window so I could listen to Bringing Down the Horse spilling into the driveway and out into the street as I biked around with friends. No music more clearly encapsulates the sound of my childhood than The Wallflowers circa 1996.

I wasn’t the only one in love with “One Headlight.” The song never got a proper single release, and based on how the charts worked in the 1990s, that meant it never actually charted on the Billboard Hot 100. But “One Headlight” was a smash regardless, topping four other Billboard charts (US Adult Alternative Songs, US Adult Pop Airplay, US Alternative Airplay, and US Mainstream Rock) and hitting the runner-up position on two others (US Radio Songs and US Pop Airplay). Writing about the Hanson chart-topper “MMMBop” back in 2022, Stereogum’s Tom Breihan classified “One Headlight” as an “asterisk” in pop music history, and speculated that the song might have gone to number 1 had it “been able to compete” on the Hot 100. As Breihan noted, such an accomplishment would have made Jakob Dylan the first person from his family tree to top the charts – something that wouldn’t be that surprising for most families, but which was mind-blowing in this context given that Jakob’s father is arguably the most lionized songwriter in history.

Much was made, during the ascendancy of “One Headlight” and The Wallflowers, of Jakob Dylan’s rock ‘n’ roll lineage. You’d expect nothing less when the son of a figure as consequential as Bob Dylan starts writing and singing his own songs. Because “One Headlight” was my first favorite song, though, I came to know of Bob Dylan first as Jakob Dylan’s dad, and not vice versa. Years later, I’d delve into the elder Dylan’s catalog and fall in love with it, and I think part of my appreciation for Bob had to do with hearing, in retrospect, the influence that he’d so clearly had on Jakob’s music. Surprisingly, most of that influence would crop up later and isn’t necessarily audible on Bringing Down the Horse. That album is so pop-rock, with tightly constructed verses, big hooks, and a clear “get to the chorus” mentality. Bob never had a “get to the chorus” bone in his body, but The Wallflowers were amazingly skilled at choruses, and it’s probably why “One Headlight” got closer to topping the charts than any single track Bob ever recorded.

Jakob would follow more in his father’s footsteps on later albums – particularly a pair of lyrical, acoustic-driven solo records he made in 2008 and 2010, respectively. But here, the clearest sign that he’s a Dylan is there in his voice. Jakob sings in a light, smoky tenor, compared to his dad’s bright, nasally baritone, but there’s something in the inflection that feels passed down. It’s a voice that ties “One Headlight” to an earlier era, and it’s probably a big part of what made the song popular among older listeners. The Wallflowers’ brand of down-the-middle, rootsy rock ‘n’ roll was, generously, two decades late, which could have easily doomed the band to irrelevance. But instead, that sound made these guys a breath of fresh air in the midst of an era dominated by grunge and alt-rock. When it came to my brother’s CD collection, I remember The Wallflowers being an extremely agreeable staple for the whole family, and I’d chalk that up to the fact that it sounds like the music from my parents’ generation. They weren’t the only boomers to go for Jakob and company, either. Just look at how ‘70s rockers took this band under their wing. Bruce Springsteen joined The Wallflowers for a performance of “One Headlight” at the 1997 MTV Video Music Awards, and Tom Petty and Jakob Dylan became such good pals that, when Petty and the Heartbreakers made it into the Rock and Roll Hall of Fame in 2002, Jakob gave the induction speech.

All these elements, I think, were subconsciously influential upon me and my musical development. For years, “One Headlight” was the barometer against which I measured all other songs. When my friends were falling in love with the nu-metal, boy band pop, and Eminem rap songs of the late 1990s, I was still hung up on “One Headlight,” and still searching for another high that felt just like it. There were other ‘90s hits that inspired a similar level of fascination in me: other cassette bootlegs I had my brother make for me included Green Day’s Dookie, Oasis’s (What’s the Story) Morning Glory, Matchbox Twenty’s Yourself or Someone Like You, and Third Eye Blind’s self-titled album, and they all had the same kind of melodic sparkle. But there was something about The Wallflowers and their almost country-leaning instrumentation – this band loved their acoustic guitars, dobro, banjos, pedal steel, and B3 organ – that intrigued me more than any of those other bands. From my later-in-life obsessions with the catalogs of Springsteen and Petty to my lifelong appreciation for folk and country-leaning rock music, so much of my musical DNA is right there in this album.

If The Wallflowers had come along in today’s cultural climate, I’m betting they would have been received very, very differently, and I’m not just saying that because their classic-rock-leaning sound would be even more out of fashion these days than it was three decades ago. Rather, I think Jakob’s status as rock ‘n’ roll royalty would work against him now in a way it didn’t back then. Recently, I’ve been surprised by the amount of venom I’ve seen directed at Gracie Abrams – someone who is, at worst, an inoffensive singer-songwriter – because she is the daughter of Hollywood filmmaker J.J. Abrams. The “nepo baby” discourse has reached such a fever pitch in culture that having a famous parent is now seen less as a point of intrigue and more as an indictment of your talent and authenticity. In this context, Jakob Dylan would likely have been laughed out of the room.

My belief? The quality of the song matters more than anything else – more than your genre, more than who your parents are, and more than what era you happen to come of age in – and “One Headlight” is a capital-G Great song. I remember, as a young kid, being so beguiled by how Jakob Dylan had stacked the lyrics with what were seemingly bald-faced contradictions: “They said she died easy of a broken heart disease”; “It’s cold, it feels like Independence Day”; “I ain’t changed, but I know I ain’t the same.” Jakob said, years later, that the song was about “the death of ideas,” and about losing your innocence and your wide-eyed hope for the world as you grow older. I don’t think I got that at all at the time, but in retrospect, it’s there in those contradictions that I pondered over. Because what’s more illustrative of losing your innocence than realizing that all the world has for you is a bunch of grey areas?

Almost 30 years after it came into the world, “One Headlight” remains a fascination for me – a deep, thoughtful, metaphor-rich song that sounds like a million bucks and still finds space for one of the most forceful choruses I’ve ever heard. To think a song like this once had the mainstream approval rating necessary to land anywhere near the top of the charts is gobsmacking, and it makes me grateful that I grew up in the era that I did. So much of who I am is because of this song. It is, frankly, the only place I could think of beginning this journey.

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