James Taylor’s Favorite Album Is Later in His Career (And More Inventive) Than You Might Think

The disconnect between what the public considers an artist’s best album and the album that the artist holds in highest regard is one of the most consistent and interesting paradoxes of the musical world. What resonates most with a creator won’t always be the same as what resonates with the beholder and vice versa, and that’s certainly true of James Taylor and his extensive, 20-album discography.

Videos by American Songwriter

When most of us think of Sweet Baby James, we think of, well, Sweet Baby James. Cuts like “Fire And Rain”, “Close Your Eyes”, and his rendition of Carole King’s “You’ve Got A Friend” have come to define his career and, more broadly, that particular era of 1970s folk. But these early albums aren’t necessarily the ones that Taylor holds dearest, as he revealed in a discography deep dive with Uncut in 2026.

One of the more surprising backstories from his albums came from Hourglass, released in 1997. Not only was this album exceptional in terms of production style. But it also saw Taylor at his most relaxed and focused, which are invaluable states of mind for recording.

James Taylor Counts ‘Hourglass’ As a Personal Favorite

To be clear, James Taylor’s fourteenth studio album, Hourglass, hardly flew under the radar. It broke into the Top 10 of the Billboard 200, albeit on the lower side at No. 9. The album also garnered Taylor a Grammy Award for Best Pop Album. Still, the tracks from this 1997 album aren’t nearly as ubiquitous as the music he put out nearly three decades earlier. But hearing Taylor speak about the recording process, it’s easy to see why he would hold this album in such high regard.

Taylor recorded Hourglass with Frank Filipetti, which the songwriter said he appreciated especially for Filipetti’s “knowledge of the actual recording process and how it sounds down on tape. Frank had the confidence and the sort of pioneering spirit, if you will, to basically make a major album for a major label, Sony, using this newly emerging home studio stuff. You could buy the whole setup that we used for about $20,000. Everything that we used in [traditional] studios, like a Neve board and tape recorder, would cost a million dollars to own.” 

With their “scrappy” $20,000 setup, Taylor and Filipetti hunkered down in a Martha’s Vineyard home that belonged to one of Taylor’s friends. The entire process took about two weeks. “We were very focused, we were very relaxed, we were in our own context, and Frank was making it happen. Some of my favorite songs are on here.”

Given the deep personal context behind many of the songs on Hourglass, it would make sense that Taylor is the most sentimental about this album. And indeed, these insights offer an opportunity to re-listen to these late-career offerings with new, Taylor-esque ears.

Photo by David Redfern/Redferns