Touchstones – October Road

In times of upheaval, I lean on touchstones–works of art that have shaped me and the continue to be sources of inspiration, influence, and solace. It might be rereading a favorite novel, a cherished poem, a movie, or (especially often) a favorite album with a good pair of headphones.

James Taylor’s Greatest Hits was released in 1976, just eight years after his debut album. It has since sold more than 11,000,000 copies – for good reason; there isn’t a song on it that isn’t a classic.

But my touchstone from James Taylor wasn’t released until 2002. October Road is full of new classics from a more settled era in JT’s life. The writing is subtle, heartfelt, and rivals any of his legendary early records. The musicianship on the album is tremendous – John Pizzarelli, Larry Goldings, Steve Gadd, and so many other great musicians. It features beautiful orchestral arrangements from Rob Mounsey and Dave Grusin.

I came to James Taylor late – I didn’t listen to him until I was well into college. But since then, he has come to embody what I think of as the peak of sincere singing. He means what he sings, and plays and sings with self-effacing enthusiasm and a palpable love for what he does, who he does it with, and who he does it for. It comes through live, and it comes through on his records.

Particularly, for me, on this album – his longevity in his art, and the winding road he has famously traveled, give the singing and playing such depth and honesty. Like all of his most recent productions, it’s recorded and mixed impeccably – his previous album, Hourglass, won Grammys for Best Pop Album and Best Engineered Album, and the production here is just as fine.

I sometimes think of James Taylor as an incognito jazz singer. He has recorded a smattering of jazz and jazz-adjacent songs over the years, of course, but more than that, he exhibits the harmonic richness, the lyric and melodic sophistication, and the interpretive freedom that I associate most strongly with jazz and jazz singing. When he released his most recent album, American Standard, we learned that he has long been influenced as a songwriter by the Great American Songbook, which lends even more credence to the idea of him as an incognito jazzer.

Tell me this song isn’t a jazz tune…

Of all his great albums, October Road is my touchstone, and it’s because of its consistency across the album, the beauty of the work, and the mood of the album. The title track gets at the mood of the whole album: it feels like autumn to me–the autumn of richly colored trees, hot cider & donuts, and bonfires. I can’t recommend the album highly enough.


Touchstones is an ongoing series of posts I’ll be writing during the COVID-19 season, reflecting on the works of art that support me in times of upheaval. I encourage you to make a list of your own “touchstones” and if you like, share them with me to publish here.