Suggesting Sinatra: Watertown

“Later that day…”

It’s a phrase that just occurred to me one day. One of the many times I was revelling in Frank Sinatra’s recordings from the late 1960s, I was struggling yet again to assimilate these wondrous sounds and assess them in the light of Frank’s more classic recordings. Once Sinatra gave in and added a modern sound to his single releases, he added another compelling dimension to his appeal as a vocalist. I felt in the songs the same glow you feel during the waning moments of your day at the beach. Or your shopping trip to the city. The height of the experience is over but a satisfied, contented sort of fatigue comes over you. You subconsciously acknowledge that the day for which you’ve been waiting so long is coming to an end and while there is a sadness that accompanies the feeling, there is also an intense wave of pleasure. I may be rambling but stay with me.

It’s later that day. The frenetic euphoria is over but something more substantial has taken its place. The glory days of Frank Sinatra the singer of hit songs could be roughy stated to be from 1953 when he arrived at Capitol Records until, say, 1966. You can trace a pivot of sorts back to the delightful “Somewhere in Your Heart” from late 1964. Later came “Tell Her (You Love Her Each Day)” and “Forget Domani” and many other minor hits that were eventually cobbled together for the misleadingly-titled Frank Sinatra’s Greatest Hits album released in 1968. Once Frank Sinatra showed the record-buying public and the industry itself that he was travelling abroad musically, wearing Nehru and singing “Little Green Apples”, songwriters began to get ideas. The majestic voice and persona of Frank Sinatra – long the one-man vanguard of jazz/pop vocal music – could perhaps be combined with the new type of song being crafted by a younger generation of composers, arrangers and producers.

From Francis Albert Sinatra Does His Thing. August 15, 1968.

Near the end of ’68, Sinatra released the nice Cycles album on which he offered “From Both Sides, Now”, “By the Time I Get to Phoenix” and “Gentle on My Mind” along with the lovely title track and majestic “Rain in My Heart”. There followed My Way (Mar. 1969), little more than an LP home for the hit single title track accompanied by “Yesterday” and “Mrs. Robinson”. Sinatra then decided to ride this contemporary wave into a project with poet Rod McKuen. Released during the fateful August of 1969, A Man Alone sported all songs written by McKuen, some delivered spoken word by Frank. Peaking at #30 on the LP charts, it was his lowest-charting album – aside from the classy record with Duke Ellington – in three years. Nevertheless, at this point, Sinatra proved ready to take on perhaps his most unique recording endeavour yet.

While it is claimed by some that the “concept album” is hard to define, I disagree. A concept album is simply any long-playing record containing songs with a similar theme or lyrical content. Sinatra may not have invented the idea but his records in the 1950s established the heights of quality to which recording in this way could ascend. In the Wee Small Hours (1955) and Frank Sinatra Sings for Only the Lonely (1958) were somber rides through a man’s dark night of the soul.

Through the 1960s, the kids had taken up the cause and concept albums and rock operas – full narrative stories that took place over the course of an LP – abounded. At the close of the 1960s, the master of the format was approached with a novel idea, one that would become his 1970 release Watertown.

A ridiculously rare and wonderful picture of the two Franks.

Two guys from Jersey named Frank. Frankie Valli (b. 1934) spent the 1960s as the lead singer of the Four Seasons, one of the two premiere vocal pop groups in the land and had recently lit out on his own, continuing to score hits. The brain trust of the music of the Four Seasons consisted of a handful of men. Bob Crewe (d. 2014) was the group’s producer and Charles Calello (b. 1938) did much of the arrangements. One of the four voices in the group belonged to Bob Gaudio (b. 1941) who had also contributed many of the group’s musical compositions. Gaudio had recently teamed with lyricist Jake Holmes (b. 1939) to create for the Four Seasons The Genuine Imitation Life Gazette, released in January of 1969. To match the tenor of the times, the record had largely discarded songs about love and instead tackled weighty subjects like war and racial tension. It was this group of men who had a project in mind for Sinatra and Valli was chosen to approach the Chairman.

I learned about these men while writing my article on the Four Seasons. My respect for their achievements and abilities grew as I dug into their story. To run into these names again while looking at Watertown was like a reunion of sorts. It served as a confirmation, too; the talents behind the Four Seasons were talents, indeed.

Promotional shot for Watertown. © Frank Sinatra Enterprises.

In New York in July of 1969, Charles Calello took an orchestra into a studio and created the backing tracks for the songs that had been written for the album. Bob Gaudio came up with the idea of setting the action in a small town and having Frank play the unlikely part of a regular guy, married with kids. Frank had not had enough time to prepare to record the songs and so did not lend his vocals to the July sessions, making this record the only time Frankie did not record live with the orchestra. He did visit the studio during the sessions but not to work. He walked up to Calello standing on a raised podium to conduct. Frank tugged on his pant leg and asked “You Calello?”. They chatted and Frank left.

While many of the concept albums of the 1960s dealt in “whimsical psychedelia”, the tale that Gaudio and Holmes constructed was concerned with more serious, adult themes. The results present a devastating story of heartbreak, disillusionment and brokenness.

The title track establishes the setting in the style of an overture. It’s definitely rock instrumentation that gets things started as bass, drums and piano make their statements before Frank as narrator ambles in. “Nothing much (is) happening” he says but he does make mention of the rain and this helps set the mood. We hear a train; “There’s someone standing in the rain, waiting for the morning train. It’s gonna be a lonely place…”. Now we know that all is not well here.

Next we are let in on it. If you’ve lived, then you know the feeling. You come away stunned, disbelieving what has happened. The setting is so benign. People enjoy respite here in the same quiet that has just brought your world to a halt. Certainly there should be a tremor to accompany something so monumental. “Goodbye (She Quietly Says)” states it gently. There should be savagery in the wound that has been opened. But nothing. “There is no great big ending, no sunset in the sky. There is no string ensemble and she doesn’t even cry. And just as I begin to say that we should make another try, she reaches out across the table looks at me and quietly says good-bye”. Our narrator has been left for dead. No answers. She doesn’t explain, give reasons. Just goodbye. Said so easily. The frustration of the unanswered questions so cruelly ignored.

Next we learn of the facade and again we can relate. The music of “For a While” has a pleasant lilt but this also is pretense, hiding our narrator’s disorientation. The listener can recall similar times when they have gotten lost in a conversation over the fence, a greeting on the street corner. The discussion of things that normally might hold some weight. But not now. Our narrator has succumbed to some of these exchanges and has almost been able to forget, to fool himself into thinking that these trite things matter. “I forget that I’m not over you. Days go by with no empty feeling until I remember you’re gone”. These inane conversations prove hypnotic, camouflaging the desolation. Until it reemerges in sharp relief.

Official Frank Sinatra

There is a certain horror when there are children involved. In “Michael and Peter”, we are introduced to the boys. There is something particularly tragic in the idea that the woman – the mother – has left. “And if you look at them both for a while, you can see they are you, they are me”. Our narrator points out the obvious when he says that the boys are the images of their parents. After all, these children were made by two people in love and planning a life together. I can only fathom a man’s helplessness looking at his sons and knowing their mother is gone. More benign conversation detailing neighbours and family and a slice of country life. We learn our narrator has worked for the railroad forever. A hard worker who has seen little reward. Maybe here is a clue to the woman’s leaving. It’s clear that he still cannot verbalize his thoughts and feelings to his wife; “Guess that’s all the news I’ve got today…maybe soon the words will come my way”. “Michael and Peter” is the most cleverly crafted of Bob Gaudio’s compositions on the album with a very astute arrangement by Charles Calello. It’s starts jauntily until it remembers that some very dark things are happening here.

An ad in Billboard for the “significant” single, “I Would Be in Love (Anyway)”. March 14, 1970.

Helplessness. In a light, breezy soft rock setting, “I Would Be in Love (Anyway)” presents perhaps the most crushing aspect of the story. Does the man feel anger? Does the man feel ripped off? Wouldn’t he just like to have it to do over again and avoid this woman and heartbreak? Sure, he would. Some of the saddest lyrics on the record tell the tale. I wouldn’t change anything. Can you believe that? He is in the blackest hole a man can find himself. This is not just drunken “One for My Baby” depression. This is ruin. And yet…

"If I lived the past over
saw today from yesterday
I would be in love anyway

If I knew that you'd leave me
if I knew you wouldn't stay
I would be in love anyway

sometimes I think, think about before
sometimes I think
if I knew then what I know now
I don't believe I'd ever change
though you'll never be with me
and there are no words to say
I'll still be in love anyway"

“Elizabeth” sounds like reverie. An interlude. An escape. A nap in the hot sun. A waking dream. Her name. “Dressed in dreams for me, you were what I wished to see…make believe was coming true” turns to “when you came to me, I found it could never be…so, a dream has to end…dressed in memories”. Listen to the final notes of this song. That is a fine creation from Gaudio and Calello. Another excellent composition is “What a Funny Girl (You Used to Be)” with that soft rock drumming prominent. The song gives us an interesting look at this Elizabeth before the thing that happened to her happened. It’s a cute picture rendered with some humour. Apparently she was quite magical, making the loss of this girl all the worse. You can see her in the kitchen sincerely trying to be a housewife and in her earnestness she was easily taken in by salesmen. All these memories…just make things worse.

Official Frank Sinatra

We get a bit of a respite here with “What’s Now is Now”. A break only in that many of us may have heard this song before on Frank Sinatra’s Greatest Hits, Vol. 2, a record with less harrowing undertones than Watertown. It’s a bright, brisk number with dramatic orchestration. But the lyrics hint at a darkness no spouse wants to consider; “Just one mistake is not enough to change my mind. What’s now is now and I’ll forget what happened then. I know it all and we can still begin again”. We’re not told what the “one mistake” was but the people in the town certainly looked down upon it, making it hard for Elizabeth to stay. The narrator assures her though that the two of them is all that matters and if she can summon the strength they can get back to where they were. This is sad on many levels. Not the least of which is that many listeners would think that so readily taking back a spouse that has perhaps made that “one mistake” is folly. This makes a bad situation worse. An excellent song with some pretty bleak lyrics. His overtures go unheard. I know it all and we can still begin again”

The end of our story comes like gathering clouds blotting an already darkening sky. “She Says” implies that our guy has talked to Elizabeth considering that the lyrics speak of the many things that “she says” to him. Of course, it’s idle small talk. There has been rain, she has lost weight, the city is strange. “She says she hopes we’re fine”. Nice of her to express concern about the boys. The ending of this brief tune suggests anticipation. Our narrator claims that she has said that she is coming home. The announcement is accompanied by a wash of relief and an exclamation from the orchestra. And then the train…

“And now the sun has broken through, it looks like it will stay”. “The Train” has perhaps the swiftest tempo of any song on the record indicating anticipatory joy. It has gorgeous chord changes played by the lightest strings. “This time around you’ll want to stay…” He’s talking to her again. It’ll be different this time. He’s had many nights to figure things out and he’s made some decisions concerning their future. The things he is still unsure of they will talk about.

"Pretty soon I'll be close to you
And it will be so good
We'll talk about the part of you
I never understood
And I will take good care of you
And never let you cry
We will look so much in love
To people passing by..."

“We will look so much in love to people passing by”. Such a sad line in this context. The whole second half of the above verse is almost too simple to be believed. Perhaps the whole tale of this album hinges on two lines of “The Train”. In the smiling midst of Elizabeth’s imminent return, out narrator drops a bombshell that may make all that has gone before dissolve in the mist; “I wrote so many times and more but the letters still are lying in my drawer”. The couplet bounces by on the wings of this otherwise optimistically rendered song. But, wait. Our narrator has spent the previous 9 songs not only reporting on Elizabeth and the whole situation but we think he’s been sharing his seemingly lucid assessment of things and his well-anchored thoughts and feelings. The listener assumes he has clearly stated things to her in one form or another, telephone or correspondence. But now we hear that he never sent the letters. Has he even talked to her at all since she left? Or has he simply folded up in a corner?

Official Frank Sinatra

The happy train song rolls on. And so does the train. The passengers are gone, the platform deserted. Confusion. “I can’t see you anyplace. And I know for sure I’d recognize your face”. As if there’s a question that maybe she was there but so greatly changed that he missed her. “I can’t see you anyplace”. She’s not there. She didn’t come home. At first I thought that she simply delivered another gut punch, saying she was returning when she had no such intention. That would be hard to take. That would be cold and cruel. But perhaps it’s worse. Perhaps our narrator has been all this time floating in a blackness no light can penetrate. Maybe he’s lost in a space that renders him immobile without even the ability to reach out to her. Maybe this has all been a dream. Maybe we’ve been privy to a man’s demented ramblings while in stupor. After all, “The Train” is jaunty and our boy sings with a certain delight about how wonderful things will be this time. Adding to the sense of madness is the way the song and the album fade away. With a gently shuffling, radio-friendly beat and a dancing oboe. And while the record spins to a close the listener is almost fooled. Wait. What just happened? The music suggests that things are right in Watertown when they couldn’t be more wrong.

The record started on the platform waiting for the train. There’d been rain. Then begins the bleak tale of misery. And all this time he has been pleading with her, beseeching her. People have been chatting to me, he tells her, without realizing that I’m not over you. What about our kids? You know they are the very images of you and I. But, gosh, honey, you know what? If we went back to the beginning, I wouldn’t change a thing. That’s how much I love you. I need you to know that. I need you to know that that was then and what’s now is now. I can forget mistakes that have been made. They belong to the past and we are moving forward. Remember the girl you used to be? Destroying the kitchen making meals for us? Ah, the joys of life. Remember? We can get back to that. Come on, honey. What do you say?

All very intelligent and admirable. But it seems it’s the same old story. A man in love with a woman who is restless. The fracture of a marriage is a real thing, though tragic, and this man is doing all he can to rectify the situation. Or is he?

The inside gatefold reads “Watertown: A Love Story” and shows a scrapbook and mementos.

See, the story’s a common one, one the listener has heard since the advent of recorded music. But something much deeper is happening here that sets Watertown apart. Maybe this is the story of a man who has lost his ability to reason. Maybe all the things that he has done to try and fix this thing – all the things we can be proud of him for – haven’t happened at all. The letters left in the drawer suggest that the narrator has spent all this time rambling to himself, completely incapable of reaching out to his wife. If he was capable, would it fix things? Who knows. But there is a certain unnerving dread in the idea that he has given up. That, despite his pain, he cannot summon the will to fix things. He is adrift. That is much sadder than your average tale of lost love.

I’ve heard Will Friedwald say that this is just a Four Seasons album with a different Frank singing but I disagree. This record could not have been made by a sweet sounding pop vocal group no matter how good. This tale called for the highest artistry. It called for a mature Frank Sinatra. So, the album could not and should not have been made any other way but – and it shouldn’t be hard to believe – there was simply no audience for this. Sinatra’s long-time fans would’ve been baffled and younger listeners would associate the Sinatra name with olden days. The original plan was to present the album as a TV special. A visual dramatization might have helped to sell this story to the public.

Watertown, the first Frank Sinatra album of the 1970’s, peaked at #101 on Billboard‘s LP charts – the first time he hadn’t cracked the Top 100. Of all of his LP’s that charted – that he recorded and released under his name alone – Watertown is the lowest-charting. By some margin. But this means nothing.

My copy. It amazes me, the records I’ve stumbled on in the wild.

I’m still surprised that singer’s of Frank’s vintage hoped to have hits in later eras when music was so vastly different and changing all the time. Reprise Records was disappointed with this record and it’s sales and this prompted them to make changes to Sinatra’s next album. Sinatra and Company, released one year later, was altered from another “theme” album – Sinatra and Jobim together again – to a record that featured bossa nova on one side and pop/rock-adult contemporary on the other. The album fared better on the charts; up to 73 or Franks’s second-lowest charting album. And then he retired. Interesting to note, though that Watertown reached #14 in the UK and Sinatra and Company hit the Top Ten of England’s album charts. Make of that what you will.

But all this means nothing. You should know by now that here at Your Home for Vintage Leisure we assess things based on how they make you feel rather than how they were received by the general public of their or any other day. And Watertown definitely makes you feel. Not only is it a real deep cut – a hidden gem, Frank Sinatra’s least successful album – but it tells the story of a real deep cut; the dissolution of a relationship and the crumbling of a man who must find the will to go on.

A spotlight was levelled on Watertown in 2022 when Reprise released a special edition with bonus tracks. There was a lot of talk around the internet regarding the record including interviews with lyricist Jake Holmes explaining the songs and the story. I deliberately avoided reading these, hoping to give my own impression of the record. Reading some of Jake’s words afterwards, I see that he and I were mostly on the same page.

For more in the Suggesting Sinatra series, see our look at his solo sides for Columbia and In the Wee Small Hours



  1. The curation of a sequence of songs to create a theme album or to create and maintain a certain feeling for the listener at home or is an interesting and probably lost art, now that we can essentially do our own thing digitally. Hearing Sinatra doing these highlighted tracks made me think of how he might have tackled the poignancy of Pancho and Lefty – perhaps in a duet with Willie Nelson…That interpretation might have been the ultimate version…

    • I very much agree. I used to even think about the two sides of a cassette when I made a mixed tape; how to start each side, end each side. “Sides” now are gone, as well. “Sequencing”? Shuffle the playlist. Sad.

  2. When I was a teenager, I had an urge to know about Sinatra. My dad hated him but I was fascinated by him for some reason. So in the early 70’s, I checked out the Sinatra section in the local record store. There was one album in it – Watertown. For a couple of years, I would check it out occasionally. Only that lone Watertown album. I eventually began listening to earlier Frank albums and really got into him. And when I finally listened to Watertown, I loved it. Great column, thanks for writing it!

    • The perspective of those that were there fascinates me. I was born in ’72, so… It would’ve been funny I guess to be curious about Frank in the 70s and go to the record store to maybe buy one of his albums. Was there only the recent ones to choose from? Or was his back catalogue always available? What would a teenager make of Some Nice Things I’ve Missed? And I cannot believe your dad hated him! Thanks for your comment.

      • He called him “Not-So-Hotra.” Also said the mob gave him a career, he couldn’t really sing! Once, as an adult, I was playing one of his Columbia recordings. My dad heard and said, “Who’s that?” Oh, his face when I told him it was Frank when his voice was at its most beautiful. Back in the early 70’s, Frank’s kind of music was dead as a doornail. I am not joking when I tell you Watertown was the only album of his in that store for years. I went to college in Chicago (I’m from Bethlehem, PA) and that’s when I found some of the Capitol and earlier Reprise stuff. I was very much past my teen years the first time I heard Some Nice Things I Missed.

      • Fascinating! I can see loving Frank or being indifferent but to hate him! Wow. How could you hear “Poinciana” or “Mean to Me” and not love the man?!

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