1996 Hit Ballad, Ranked Among 'Greatest Adult Alternative Songs of All Time,' Was Written by a Teenager
Technically, the Wallflowers had their biggest hit with "One Headlight," which went to #1 on the Billboard Adult Alternative chart and #2 on the Billboard Hot 100 in 1997. But their breakthrough hit was the first single off that same album, Bringing Down the Horse: "6th Avenue Heartache," released in April 1996.
As anyone who was around back then can tell you, the song made a huge impression that spring. Not only was "6th Avenue Heartache" on the radio all the time, but the video played nonstop on MTV, quickly catapulting Jakob Dylan to music heartthrob status. Plus, the song featured the familiar voice of Counting Crows frontman Adam Duritz on backup vocals.
With all that in mind, it's not surprising to learn that "6th Avenue Heartache" was nominated for Best Rock Song and Best Rock Performance at the 39th Annual Grammy Awards, or that it was ranked #37 on Billboard's list of "Greatest Adult Alternative Songs of All Time."
What is surprising, on the other hand, is the fact that Dylan was only 18 years old when he wrote the future hit.
According to American Songwriter, Dylan called "6th Avenue Heartache" the first "serious song" he ever wrote. At the time, he was 18 years old and living in New York City, where a homeless man often sat outside his window playing music. After the man disappeared one day, his things began getting taken away by people. The lyrics were inspired by Dylan's feelings at the time:
Look out the window, down upon that street
And gone like a midnight was that man
But I see his six strings laid against that wall
And all his things, they all look so small
I got my fingers crossed on a shooting star
Just like me, just moved on
The video for '6th Avenue Heartache' was directed by David Fincher
As mentioned above, the video for "One Headlight," "6th Avenue Heartache" was an MTV mainstay. A mix of performance scenes and narrative clips illustrating the song's story, the video was helmed by David Fincher (of Se7en and Fight Club fame).
As Dylan explained in an interview, Fincher got a tape of the song before the record was out.
"He got a preview of the record - an advance copy," Dylan said, per Power Pop Blog. "He had heard that this was going to be the new single, and he actually called us and said he was interested in doing it, if we were interested. So we thought about it and we were like, what else have you done."
Clearly, Fincher was up for the task.
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This story was originally published May 20, 2026 at 6:03 PM.