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4. Neko Case: “Star Witness”
“Writing a song starts in the middle of a world you haven’t invented yet,” Neko Case says in her recent memoir — an apt description from a musician whose songs all seem like transmissions from uncanny but strangely familiar alternate realities. I love her idiosyncratic approach to structure and melody, her sense of atmosphere and the haunting, impressionistic imagery that she conjures on some of her best songs, like this one from her magnificent 2005 album “Fox Confessor Brings the Flood.”
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5. Frank Ocean: “Ivy”
Frank Ocean’s music is in constant tension between its cool-guy bravado and its disarmingly tender vulnerability, a balance he strikes brilliantly on this crooned highlight from his shape-shifting 2016 opus “Blonde.” Though he’s not as prolific as some other songwriters on the list (especially given the fact that he hasn’t released new music in nearly a decade), Ocean’s creative outpouring in the 2010s remains rich and resonant enough to make him, still, one of the defining songwriters of his generation.
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6. Wilco: “I Am Trying to Break Your Heart” (Jeff Tweedy)
As Wilco has gradually evolved from alt-country upstarts to arty minimalists to the elder statesmen of American folk-rock over the course of several decades, the warm, fractured and unmistakable songwriting voice of the frontman Jeff Tweedy has been perhaps the only unifying thread throughout the band’s many lives. This dreamlike incantation that kicks off the band’s great “Yankee Hotel Foxtrot” is somehow simultaneously airy and airtight.
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7. Billy Joel: “Vienna”
Look, I know he’s divisive, and I know he’s written some stinkers (the most notorious of which I happen to love) — but he’s Billy Joel! There’s something quintessentially American about his blend of compositional sophistication and Long Island grit; call him the Beethoven of Hicksville. The fact that this ballad of tough-love wisdom continues to resonate with younger generations is proof not only of his enduring appeal, but of his deep connection to the elemental anxieties that make us hopelessly human.
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8. Tom Waits: “Time”
A bar stool poet with the voice of a sanctified corpse, Tom Waits knows as well as any living American writer how to repurpose the sorts of words, sounds and sentiments found in our national gutter into songs of surreal beauty. This ballad from one of his finest albums, 1985’s “Rain Dogs,” is enough alone, in my mind, to punch his ticket into the tower of song.
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9. Hurray for the Riff Raff: “Pa’lante” (Alynda Segarra)
Alynda Segarra, who records as Hurray for the Riff Raff, is remarkably well versed in an American musical history that they carry lightly enough to subvert, whether that means defiantly rewriting an old murder ballad to center the perspective of the dead or using the traditional tools of a folk singer-songwriter to meditate on the modern horrors of ecological collapse. Segarra delivers this fiercely written manifesto of Puerto Rican pride, from their 2017 album “The Navigator,” with stirring conviction and the visionary power of a great artist.