Frank Sinatra was always one to face the world head-on. So it was with his turning 50. The man who had pioneered the “concept album” with a string of themed records for Capitol began thinking of an LP that would allow him to plant his feet squarely in the present, 1965, and reflect with every ounce of experience he’d acquired in the many lives he’d led over a mere 50 years. The album that would become September of My Years began its life inspired by Kurt Weill and Maxwell Anderson’s “September Song.”  Introduced by Walter Huston in the 1938 musical Knickerbocker Holiday, it may be the ultimate musing on mortality, delivered by an older man addressing a young woman.  With the rueful “September Song” in his mind, Sinatra enlisted Gordon Jenkins to arrange and conduct, and the team began to craft an album which would stand among Sinatra’s finest, whether at Capitol or Reprise. It also may be one of the quintessential late-night albums, perfect for listening while nursing a nightcap in the dark. The fruit of Sinatra and Jenkins’ labors has been reissued this week in a deluxe edition by Concord and Frank Sinatra Enterprises (CRE-32415) as part of their ongoing Frank Sinatra Collection.

Jenkins’ approach was a straight-ahead one: match Sinatra’s resonant vocals with a lush bed of strings, strings and more strings. This style is laid out on the album’s first two tracks, and it’s immediately clear that this would be a different kind of Sinatra album. Sammy Cahn and Jimmy Van Heusen’s title song has none of the brash swing of their “The Tender Trap,” “Come Blow Your Horn” or “Come Fly with Me.” (Nor is it as bleak as two of their torch songs which also gave Sinatra album titles, “Only the Lonely” and “[When] No One Cares.”) Instead of boasting finger-snapping brio, “September of My Years” is a truly lovely, elegiac meditation, sung with sensitivity. Jenkins’ own “How Old Am I?” follows, with Sinatra answering wistfully.

Yet the album’s centerpiece was a song which epitomized one of Sinatra’s central dichotomies. The man was a forceful, larger-than-life personality, yet he sang with an intimacy so real, you believed he was singing to only you. “It Was a Very Good Year” was a gentle folk tune penned by Ervin Drake (best-known for Broadway’s What Makes Sammy Run? starring Sinatra pal Steve Lawrence) in 1961 for The Kingston Trio’s Bob Shane. Jenkins’ grandiose and anthemic resetting added tension and color to the song, replacing simple guitar strumming with majestic violins. It would have hardly been believable for most singers, but Sinatra was never “most singers.” Nobody could have been surprised when the transformed “It Was a Very Good Year” won Sinatra a Grammy for Best Male Vocal Performance and Jenkins a trophy for arranging. (The top prize, Album of the Year, would also be snagged by Sinatra and producer Sonny Burke for September of My Years.)

September of My Years’ initial idea may have been simple, but its execution was anything but. In addition to “How Old Am I?,” Jenkins contributed his own “This is All I Ask.” Other songs brought to the project share the moody, contemplative ballad tempo. Some tracks were brought from Broadway, including songs previously recorded by Sinatra at Columbia, an era that must have seemed like a lifetime ago. His poignant new takes on “Hello, Young Lovers” and “September Song” bore little relation to the sweeter originals. Charles Strouse and Lee Adams’ “Once Upon a Time” was a show song of more recent vintage from their Mel Brooks-penned musical All-American, while Sinatra tapped the Alec Wilder songbook  for “I See It Now.” The singer had previously expressed his fondness for Wilder’s work via an entire set which he conducted (and beautifully) on a rare trip to the podium, and “I See It Now” fit perfectly on September.

Another Grammy was taken home by a young writer named Stan Cornyn. As with the Concord/FSE reissue of Sinatra/Jobim, Cornyn has penned new notes. What a treat they are! While Cornyn’s hipster style may be an acquired taste, he has lost none of his touch and brings a “you are there” quality to his writing. His lengthy essay, incorporating the original 1965 notes, makes an already-vivid listening experience into something even greater.

The 2010 edition of September offers two bonus tracks. Unfortunately one has already appeared on CD, a June 1984 live recording of “This is All I Ask,” previously issued on the Reprise/Rhino box set Sinatra: New York. That said, it’s a fascinating comparison to hear Sinatra reinterpret the song some twenty years later, when its themes may have rang even more true. Like any great actor, Sinatra brought his entire body of experiences to the song each time he performed it, and so it’s imbued with a different, perhaps sadder, more haunting feel than the original. The other bonus track is very welcome and a true rarity, the 1968 single version of “How Old Am I?” with an overdubbed guitar part. (Its A-side, “I Can’t Believe I’m Losing You,” still remains unavailable on CD, and would be an ideal candidate for future release.)

This reissue, produced by Charles Pignone, has been remixed by Larry Walsh, who has done the honors (sometimes controversially) for all of the albums in this series. The remix is subtle and it’s a pleasure to discover new aspects of the recording on multiple listens. Dan Hersch at DigiPrep handled the mastering. While opinions wildly vary in audiophile circles about Sinatra’s catalogue and its many versions, the Walsh/Hersch disc was somewhat preferable to these ears to the 1998 Reprise remastering by Keith Blake. (Oddly, Blake is credited with “digital mastering” on the back cover of the new CD, while the Walsh/Hersch team is credited inside.  It’s likely that Blake’s credit is inaccurate.)

All of Sinatra’s Reprise-era albums deserve to be in print in the U.S. in expanded editions such as these. However easy they are to order, it’s a crime that the (more or less) complete Reprise catalogue is currently available only in Europe and not in the country of Sinatra’s birth. One wonders, too, whether Concord/FSE has ever considered a “Bootleg Series”-type collection or box set to allow more unreleased material (alternate takes, session material, etc.) to come to light. Fans of September should be aware of a CBS-TV film that preserves the recording session in which Sinatra tackled “It Was a Very Good Year.” While it’s somewhat disappointing that this footage couldn’t be made available as a bonus disc for this reissue (wouldn’t that have been definitive!) it is easily located on the VHS Sinatra: Off the Record (Fox Video, 1998). And for a look at the other side of Sinatra circa 1965, check out Universal U.K.’s first-ever CD release of Sinatra ’65, featuring a number of his more pop-oriented sides from that year. Those Ernie Freeman-arranged tracks, emphasizing the beat and a backing chorus, are about as far removed from September as possible.

September of My Years remains a touching reminder of why Frank Sinatra remains perhaps the finest interpretive singer of all time; more stellar concept albums would follow (the Bob Gaudio/Jake Holmes-written Watertown may be the most fascinating), but this 1965 gem resonates as one of the most personal, and therefore one of the most universal.