The Grammys have a long and well-deserved reputation for delivering make-up awards, honoring artists whose work the Recording Academy largely (in some cases entirely) ignored in their prime, honoring current releases that pale in comparison to the classic records that the Grammy voters shrugged at back in the day. One of many such examples is James Taylor’s 1997 Best Pop Album Grammy for Hourglass, a solid if not especially notable second-half-of-his-career album from a guy who put out half a dozen stronger ones prior to that.
In the media run-up to its release, veteran soft rock singer-songwriter Taylor characterized Hourglass as a collection of “spirituals for agnostics,” and it’s easy to appreciate how that phrase captures the essence of not just this album, but Taylor’s entire catalog of warm, observant, penetrating and piquant songs exploring the nature of solitude and friendship, alienation and love, tragedy and comedy, life and death. Whether he’s firing off goofy wisecracks or engaging in harsh self-critiques, Taylor has a way of endearing himself with earnestness even as he’s knocking you back on your heels with honesty.
Hourglass capped something of a mid-career renaissance that had seen Taylor’s fertile ’70s run followed by a more fallow period in the ’80s, leading up to a resurgence with 1991’s sparkling New Moon Shine and 1994’s double-disc concert collection Live, capturing his by-then polished-to-perfection live show. It also marked JT’s first album in 18 years without Don Grolnick, whose tenure as his main keyboardist extended back to Flag (1979) and who had over time assumed the role of musical director and then also producer on Taylor’s previous two studio albums. 
Hourglass is dedicated to Grolnick, who died of lymphoma on June 1, 1996.
The highlights from this album—produced by old pro Frank Filipetti—arrive early and often, and center on two recurring Taylor themes: frank examinations of his own troubled family history, and looming mortality. The two intersect most memorably on “Enough To Be On Your Way,” in which Taylor zooms in on the funeral for his older brother Alex, who died in 1993 at just 46 after downing most of a bottle of vodka. Its penetrating tone is an echo of “That Lonesome Road,” “Never Die Young,” and even “Fire And Rain,” earlier Taylor songs addressed to friends gone too soon, and while it’s addressed to a fictional “Alice,” it’s a thin veil for a song that Taylor has stated is indeed about his brother. Notable also is the way its opening couplet—“The sun shines on this funeral / The same as on a birth”—subtly calls back to Taylor’s early hit “Sweet Baby James,” written about the birth of Alex’s son James.
Other highlights include the rascally-sweet love song “Little More Time With You,” featuring a superb harmonica solo from guest Stevie Wonder, and the somewhat ironically upbeat “Jump Up Behind Me,” about the time his father drove up from Chapel Hill, North Carolina to New York City to rescue him from a bad situation after the collapse of his early group The Flying Machine. The latter’s follow-up “Another Day” pays glowing tribute to a new dawn: “The sun has begun / To melt all our fears away / Another day.”
Elsewhere on the album, Taylor mixes in fairly typical-for-him numbers reveling in the beauty of nature (“Gaia”), finding solace in travel (“Up Er Mei”), playfully poking political villains (“Line ’Em Up” zooms in on the goodbye party Richard Nixon threw for himself in 1974), and calling back to the pop standards of his youth (closing cover “Walking My Baby Back Home”). All are rendered with the requisite gentle shine applied by Taylor’s crack band, at this point anchored by Clifford Carter (keys), Jimmy Johnson (bass), Carlos Vega (drums) and Bob Mann (guitars), with a stellar vocal chorus of Valerie Carter, Arnold McCuller, Kate Markowitz and David Lasley.
Said shine is further burnished by a steady queue of guests including Branford Marsalis, Michael Brecker, Shawn Colvin, Yo-Yo Ma, Sting, and the aforementioned Stevie Wonder. Was it their star power, the intensity of the album’s themes, the comforting familiarity of JT’s soothing voice, or just good timing and a sentimental vote that won Hourglass a Grammy? Who can really say? What can be said is that while Hourglass ranks near the middle of the pack in terms of Taylor’s overall catalog, it certainly displays all of the characteristics that have won him a loyal multigenerational following: warm melodies, crisp arrangements, and lyrics that are alternately raw and poetic, offering a penetrating perspective on the moments that shape the arc of our lives.