The October of His Years: Sinatra’s Watertown at 50

Once seen as an anomaly in his catalog, a half century of fermentation sees a newfound respect for the Chairman’s dark masterpiece

Frank Sinatra Watertown Collage I (Art: Discogs)

Wasn’t it enough to simply be Frank Sinatra, to carry all the undying affection of an entire generation, to represent everything the post-WWII American man aspired to be?

Sinatra was not supposed to have an identity crisis, and yet there he was, only in his mid-50s as the 1960s were ending, and he was floundering around, not entirely certain where he fit in, making the kind of creative mistakes that the young Sinatra – the one who bristled when Mitch Miller at Columbia foisted subpar material on him – would have brushed off as entirely unworthy. He allowed himself to be talked into an album entirely composed by Rod McKuen; he filmed, in 1969, a movie called Dirty Dingus Magee; there was a television special, Francis Albert Sinatra Does His Thing, where he wore a spangly, ruffled Nehru suit and sang Laura Nyro’s “Sweet Blindness” with the Fifth Dimension. There was “My Way,” and a lot of people love that, but really? “I did what I had to do, and saw it through without exemption”? His last good album, a brilliant one actually, was the one he did with Antonio Carlos Jobim in 1967.


VIDEO: Frank Sinatra and 5th Dimension perform “Sweet Blindness” on Francis Albert Sinatra Does His Thing

Look, I get it: it was a rough time to be a mainstream singer of popular songs, and most vocalists in Sinatra’s sphere adapted by trying to appear “with it.” They knew what was happening, baby, or at least pretended to. Barbra Streisand’s wacky What About Today? found her struggling with “With a Little Help From My Friends” and Paul Simon’s “Punky’s Dilemma.” Sammy Davis Jr made an album for Motown with “Spinning Wheel” and “You Better Sit Down, Kids.” At Columbia, the entire MOR roster plundered the pop charts. Lena Horne did “Rocky Raccoon.” If rock had “grown up,” in a post-Sgt. Pepper paradise, to the point where the record album was taken seriously as a mature artform, where did that leave the actual grown-ups, the artists who thought they were making artful music geared towards an adult audience?

Sinatra didn’t know. His My Way album did just fine on the strength of the title track, but his contemptuous take on “Mrs. Robinson” showed how skeptical he was about kid music. The McKuen project, A Man Alone, arranged, like My Way, by Don Costa, probably confused the hell out of Sinatra’s core demographic, who might not have wanted to hear him recite McKuen’s poetry. But instead of recalibrating and going back to the Great American Songbook, or looking for new songs that might have suited him (one might have longed for a Frank Sinatra Sings Randy Newman album: “Lonely at the Top” was supposedly pitched at one point), the next Sinatra project was a song-cycle called Watertown, recorded in 1969 and released in March 1970.

The story goes that Sinatra was chatting with fellow Jersey boy Frankie Valli, the conversation turned to songs, and Valli thought that Bob Gaudio – the Four Seasons’ primary writer – might have some material for the senior Frank. The most recent Four Seasons album was an ambitious departure for the group, written by Gaudio with Jake Holmes, The Genuine Imitation Life Gazette, arranged by Charlie Calello, but there’s no reason to assume Sinatra was familiar with it; he probably just knew the Seasons had hits. Gaudio and Holmes demoed up the Watertown material and sent it off, and Sinatra said, sure, he’d do the whole megillah, and not only that, there’d be a tie-in television special. Give Sinatra points for diving into this concept. It’d have been simpler to do what Andy Williams was doing, finding ballads that had gotten on pop radio, sticking with the formula (Williams, around the same time Watertown was being recorded, was experimenting with his own sort-of concept album designed by Mason Williams, which made up one side of the Raindrops Keep Falling on My Head LP). Watertown is about a guy, a working man, whose wife has left him and their two sons, and the songs are about the break-up, the despair, the loneliness, the (spoiler) false hope of romantic reconciliation. The narrator is trying to make some sense of why things went bad (Sinatra and Mia Farrow had divorced the year before, and you can hear the Watertown text as reflecting his own situation).

Frank Sinatra Watertown collage II (Art: Discogs)

The album was unlike anything Sinatra had put out before. There was a sketch on the cover that gave nothing away (it might have done better if it were a stylistic update of In the Wee Small Hours, with a drawing of Sinatra as the narrator waiting at the train station). Musically – the arrangements were by Calello – it felt elusive; the songs, for the most part, don’t have real choruses; they’re more mood-pieces, and Sinatra sells the mood, bleak and ruminative. And, no surprise, the album flopped. For the first time in his career (except for an album of patriotic songs where he shared billing with Bing Crosby and Fred Waring’s Pennsylvanians), an LP of new Sinatra material didn’t make the top 100. There was never a TV special, which one imagines as a kind of sequel, fifteen years later, to the Sammy Cahn-Jimmy van Heusen adaptation of Our Town, where Sinatra played the Stage Manager. 

Watertown was the last full album Sinatra made before his 1971 “retirement” (Sinatra & Company was compiled from a second Sinatra-Jobim session and random sides, including a Gaudio-Holmes outtake “Lady Day,” rearranged by Costa). Over the years, it has achieved something of a reputation-reversal, with devotees proclaiming it a lost masterwork. The reappraisal feels like an over-correction: I’ve seen writing on Sinatra websites raving about the album and, in the comments, responses like “Your piece made me eager to give Watertown another chance. It’s still terrible.” It’s not: Sinatra is in fine voice, and his readings are subtly moving. You can always tell when he’s personally invested and when he’s got one foot out the studio door, and even though he is, for the first time, singing over pre-recorded tracks, the commitment is there.

But damn, is this a soggy album. The narrator is like a meteorologist: “Far as anyone can tell/The sun will rise tomorrow,” Nothing much happenin’ down on main/’Cept a little rain,” “This spring we had some heavy rain/By summer it was dry again,” “She says the weather’s cold/She says there’s been some rain,” “Just can’t have you comin’ home/On such a rainy day,”

“The sun has gone and now my face is wet with heavy rain.” There’s some exceptional clunky writing here. “I never ever met a person more sincere/You’d always listen with an open ear” is like something you’d find in a middle-school yearbook. Still, compared to some of the stuff he recorded after his 1973 comeback, on Ol’ Blue Eyes is Back and Some Nice Things I’ve Missed, Watertown is, at least, a serious attempt to find a place in a musical climate that he didn’t quite trust or understand. Like his character in Watertown, Frank Sinatra was at a crossroads, not quite grasping how he found himself in these circumstances, wondering how his story was going to turn out.


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Mitchell Cohen

RockandRollGlobe contributing writer Mitchell Cohen began writing about music and films for various publications in the mid-’70s, including Creem, Film Comment, Take One, Fusion, Phonograph Record Magazine. He is the co-author of Matt Pinfield’s memoir All These Things That I’ve Done, and a contributor to the website Music Aficionado. Follow him on Twitter @mitchellscohen.

2 thoughts on “The October of His Years: Sinatra’s Watertown at 50

  • July 17, 2020 at 9:47 pm

    Watertown was bold and daring
    Unlike other songs with rock beats thrown in to be current, the straight eighth feel works here.
    With a tv special, Sinatra finds a new audience

    • April 29, 2022 at 3:12 pm

      Any time Sinatra took a chance outside the box people put him in, small contracted minds gave him bad press. Sing and Dance, Close to You, All Alone, Francis A, A Man Alone, Watertown, parts of Ol Blue Eyes and The Future from Trilogy all had dreary dopes complaining.
      A Beethoven or a Mozart of his time, years after he’s gone everything he did sounds profound. We go along and learn Bach or Liszt because they are Masters; so is Sinatra. Appreciate him.


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