Frank Sinatra’s forgotten masterpiece Watertown

Frank Sinatra - Las Vegas (

Frank Sinatra – Las Vegas


In March 1970 Frank Sinatra released the album Watertown. Supposedly, it sold so bad it partly triggered Sinatra’s sabbatical a year later. Once again proof that sales numbers alone don’t necessarily equal the quality of the content. In 2010 I bought the remastered cd version of Watertown, a true masterpiece.

Frank Sinatra

On December 12th, 1915, Francis Albert Sinatra was born in Hoboken, New Jersey, as the only child of two Italian immigrants (he was enlisted as Frank Sinestro, an error on the part of the municipality, which he corrected in May 1945). During his childhood years he spent a lot of time at his parents’ diner, where he started to sing as a means to to acquire some pocket money.

A young Frank Sinatra (

A young Frank Sinatra

He developed a strong preference for big band jazz and was a huge fan of his big idol Bing Crosby. He left school when he was only 15 years old and worked wherever they would have him. In the meantime he sang and in New York his talent was discovered. Following a number of local successes with and without a band, he made his first recording in March 1939. In June of that same year he was offered a contract by band leader Harry James, providing him with the much needed experience, but success was lagging. In November he joined the Tommy Dorsey band. It turned out to be the right move at the right time, Sinatra and Dorsey learned each other what they knew. Sinatra picked up his famed perfectionism from Dorsey.

But Sinatra wanted more, in January 1942 Dorsey allowed Sinatra to do some solo-recordings. The recordings turned out so good that Sinatra became convinced he had to pursue a solo career. However, Dorsey had made a deal with Sinatra and refused to let him go. Following a lawsuit, Sinatra said goodbye to Dorsey on September 2nd, 1942. Dorsey’s last words: “I hope you fall on your ass”.


On December 30th, 1942, Sinatra staged his first show as a solo artist. The audience, mainly made up of young women, was frenzied. A new phenomenon was born: a young audience coming in drones to see an artist. Sinatramania was used to describe the magnetism Sinatra seemed to have over his audience. His nickname The Voice stems from this period.

Sinatramania (



On June 1st, 1943, Sinatra signed a deal with Columbia Records. He recorded a lot of songs, which all were very successful, started to perform in movies and played many radio shows. In 1946 his first album The Voice Of Frank Sinatra was released, which shot to the number 1 position on the Billboard charts. Subsequent albums were equally successful, but from 1949 onwards his success started to decline. Enter Las Vegas. He was able to make a lot of money there by performing at the hotels. In September 1951 he started at the Desert Inn and the Riverside Hotel. From that moment on Frank Sinatra and Las Vegas were inextricably linked to each other.

But his popularity was on the decline. At times, venues were half empty and in 1952 Sinatra was released from his contract with Columbia Records.

Frank Sinatra - In The Wee Small Hours (

Frank Sinatra – In The Wee Small Hours


On March 13th, 1953, Sinatra signed a 7 year deal with Capitol Records. He met Nelson Riddle, arranger and conductor, and Nat King Cole’s primary musical partner. Once again, Sinatra had a chance encounter that was hugely important to his career. The album Songs For Young Lovers was the first result and it was very fine indeed! Many fabulous albums followed: Swing Easy! (1954), In The Wee Small Hours (1955), Songs For Swingin’ Lovers! (1956), Close To You, A Swingin’ Affair!, Where Are You? (1957), Come Fly With Me, Frank Sinatra Sings For Only The Lonely (1958), Come Dance With Me!, No One Cares, Nice ‘n’ Easy (1960), Sinatra’s Swingin’ Session!!! and Come Swing With Me! (1961). In 1962 his Capitol Records period was closed with the release of the album Point Of No Return.

Reprise Records - Logo (

Reprise Records – Logo


Sinatra badly wanted his own label and tried to buy Verve Records, but failed. Upon which he decided to start his own: Reprise Records. The ultimate goal was to provide artists with complete artistic freedom and to let them own their music.

Reprise Records was very successful after it was sold to Warner Bros. in 1963. Sinatra kept a 1/3 share in Reprise, which turned mega in the 1960s and 1970s, giving a home to artists like Jimi Hendrix, Neil Young, Joni Mitchell, Frank Zappa, Emmylou Harris, T. Rex, The Meters, Fleetwood Mac and Beach Boys.

The first album on his own record label was Ring-a-Ding-Ding!, a big success, followed by Sinatra And Stringsin 1962, a highlight in his career. In 1963, back together with Nelson Riddle again, he released The Concert Sinatra. In 1966 Sinatra released That’s Life followed by Strangers In The Night. That same year Sinatra released his first ever live album, Sinatra At The Sands, which saw him being accompanied by the Count Basie Orchestra conducted by a still (very) young Quincy Jones. One of the very best live albums of all time.

At the end of 1968 Frank Sinatra recorded a song Paul Anka had written with him in mind, My Way (using the melody of Comme d’Habitude). After a slow start it became Sinatra’s greatest hit. However, his album sales were swindling. His film career was falling behind as well.


Frank Sinatra - Watertown (

Frank Sinatra – Watertown

In March 1970, Frank Sinatra was 54 years old, his Watertown album was released. In order to keep in touch with the ‘modern’ audience, Sinatra had previously recorded songs by contemporary song writers and musicians, including Simon & Garfunkel and The Beatles. On this album he worked with Bob Gaudio (a member of The Four Seasons) and Jake Holmes, a song writer hailing from San Fransisco.

Recordings for the album took place from July 14th to October 31st, 1969. The instrumental pieces were recorded in New York, with Sinatra present at the studio. Contrary to his usual way of working, he didn’t record his vocals at the same time as the music. They were recorded at a later time in Hollywood (a first and last, Sinatra would never repeat it again).

Concept album

The album is a so-called concept album, portraying the story sequentially. Earlier Sinatra albums, like In The Wee Small Hours and Only The Lonely, can be interpreted as concept albums, not because of the story, but rather for the overall theme: sad, melancholy songs performed with conviction.

The story of Watertown is about a man, who’s is left behind by his wife, who raises his kids in the small town of Watertown.


By the time the album was released on cd in 1994, Jake Holmes told the story song by song:

  1. Watertown: It was the set-up for everything that followed. I had in mind as a model Lazy Afternoon. I wanted a languid feeling. If we had done the TV special, it would have opened it up, with the credits going by.
  2. Goodbye (She Quietly Says): I had a line in my head. “There was no tempest in the tea”. That’s what led me there. I love the idea of those kind of goodbyes that people have where nothing is happening emotionally. It knocks me out when there is nothing on the surface. People are just sitting in a coffee shop and devastation has happened. They don’t articulate their feelings. Instead, they are putting sugar in their coffee and spooning cake. They are having a quiet conversation but meanwhile a life is coming apart.
  3. For A While: I’ve always felt that there is that moment in your life when you forget about something that is really terrible. For five minutes the sun is shining and everything is beautiful. Then all of a sudden you realize that the person you cared about is gone, and it all comes back. It is one of those horrible things about grief – one of those little holes in grief when it becomes even more painful.
  4. Michael & Peter: I had lost a child in my first marriage. I would have had a child by myself if I could have (laughs). I desperately wanted kids. In a funny kind of way, Gaudio’s kids were the models for that song. I put it in letter form, because it was the only way the guy could articulate those sentiments to her.
  5. I Would Be in Love (Anyway): I guess it’s that you can’t regret where you are even if life takes you someplace where you don’t want to be. In a strange kind of way, it was this guy trying to let go of this woman without being angry with her. You know, throughout the story, he was never really angry at her. He kind of understood; she had to go.
  6. Elizabeth: It was real simple. I just love that name. Bobby was writing the song and that word just fell into the melody. I just imagined a girl named Elizabeth and wrote words that were a tribute to her.
  7. What A Funny Girl (You Used To Be): The album could have been a little bit maudlin and dour. I was trying to put a little bit of sunlight everywhere I could. It was a retrospective song. I also wanted to indicate in the song that they had been childhood sweethearts. I wanted that kind of an idea. They were probably kids together. I wanted to give the sense that they had gone to school together. They had fallen in love and married quite young.
  8. What’s Now Is Now: There is in that song an indication that she had obviously gone with somebody else. She has had a relationship, and he hadn’t been able to accept it. That is partially what drove her off to the big city. There is a guilt theme in that song. It is the song that opens up the story.
  9. She Says: The song is a triple turn to me. He is suspicious of the small talk. The kids are echoing his fears. Why is she sending this letter? What is going on? It is such good news; they can’t believe it and they don’t trust it. The twist is her saying, “She’s comin’ home”. They don’t trust that either.
  10. The Train: … is the story. We find out that he really didn’t communicate anything to her, and she isn’t coming back. Although we’re getting all of this story from him, she never got any of this. If she had heard this album, she might have come home. She never saw this side of him. When I think about this in retrospect, there is so much that is not done. There is so much that is unfinished. It gives the story a very deep resonance.

The 1994 cd release contained an extra song, Lady Day, telling the story of the day the woman left Watertown to head to the city.

  1. Lady Day: I saw the woman as someone who had talent. She wanted to be an artist or a singer. He was a hometown person. His whole orientation was family and business. He was the kind of guy who really lived in Watertown. She was more restless – a more contemporary woman. She wanted to do other things. She wasn’t liberated enough to tell him, and she didn’t think he’d understand. He was basically a good guy, but she wanted more. She abandoned her family and went for a career. The postscript was whether or not she got it and was it worth it.

Despite the songwriter’s explanation, some listeners still hold on to their view that the woman in the story didn’t leave the main character. They’re convinced she has passed away. As plausible as the theory may seem, I stick with the story as told by the actual writer.

Frank Sinatra - Watertown - Gatefold (

Frank Sinatra – Watertown – Gatefold

Michael & Peter

The way Sinatra sings the songs, clearly demonstrate the main character’s sorrow, despair and disbelief. It’s very impressive the way Sinatra is able to put emotion into every syllable. Many listeners cite Michael & Peter, which serves as a (musical) letter to his former wife, as the main emotional breaking point:

Michael is you, he has your face
he still has your eyes remember
Peter is me ‘cept when he smiles
And if you look at them both for a while
you can see they are you, they are me

This spring we had some heavy rain
by summer it was dry again
the roses that we planted last fall
climbed the wall

I think the house could use some paint
you know your mother’s such a saint
she takes the boys whenever she can

The combination of melancholy, seeing the other though your children and the triviality of the weather and jobs around the house intensify the emotion even more.


Frank Sinatra - I Would Be In Love Anyway (Billboard 14-03-1970) (

Frank Sinatra – I Would Be In Love Anyway (Billboard 14-03-1970)

The collaboration with pop-writers led to Sinatra receiving a lot of flak, because the purists said pop was unworthy of him, the reviewers didn’t understand any of it and the buying audience didn’t pick up on the album, because it was all kept pretty low key. Also, Sinatra didn’t do any marketing or promotion in support of the album. A planned (movie)special was canceled (due to the lack of interest, or maybe it was the other way round?). Anyway, it turned into the worst selling album of Sinatra’s entire body of work. It is said that a mere 35,000 copies were sold a year after its initial release.

But the purists, reviewers and audience were wrong: Watertown is a phenomenally beautiful and sincere album, on which Sinatra uses his impeccable timing and ‘feel’ to the max. Nowadays, Watertown is recognized as such.

The album comes highly recommended. Even though the emotion can be overwhelming at times, the beauty is unmeasurable, the feeling is so real, it can only lead to once obvious conclusion: Watertown is a masterpiece that every music lover has to know.

Watertown may be the saddest album of Sinatra’s entire body of work, maybe even of the history of (pop)music, but its beauty, emotion and surrender command immense respect.


All songs written by Bob Gaudio and Jake Holmes.

  • Watertown
  • Goodbye (She Quietly Says)
  • For A While
  • Michael & Peter
  • I Would Be In Love (Anyway)
  • Elizabeth
  • What A Funny Girl (You Used To Be)
  • What’s Now Is Now
  • She Says
  • The Train

The 1994 cd re-release contained the extra song Lady Day.

Frank Sinatra - Relaxing/Sabbatical? (

Frank Sinatra – Relaxing/Sabbatical?

After Watertown

Following the disastrous sales numbers and the lukewarm reception of Watertown, Sinatra also left the Las Vegas hotel Caesars Palace (rumor has it he left after manager Waterman threatened him with a gun). He did some shows in England with Count Basie, and made his last recordings for Reprise in November, which were released in March of 1971 on the Sinatra & Company album. He subsequently announced his retirement and in June of 1971 he performed for the last time in Hollywood.

It soon became apparent that his retirement was nothing more than a planned sabbatical. Sinatra hadn’t planned anything beyond taking time off for about 12 months. He made his comeback in September 1973 with a television special (entitled Magnavox Presents Frank Sinatra) and a new album: Ol’ Blue Eyes Is Back. It was a success, sales were great, as were the reviews. He even returned to Caesars Palace in the beginning of January 1974. He went off on an elaborate world tour (documented on the 1974 live album The Main Event – Live). Sinatra performed regularly during the following years.

Frank Sinatra - Trilogy: Past Present Future (

Frank Sinatra – Trilogy: Past Present Future

Following a six year drought, Sinatra released Trilogy: Past Present Future, a three-double album, in 1980. In 1981 he performed at Sun City, going against the cultural boycott against South Africa’s apartheid regime. In 1982 Sinatra signed a deal with the Golden Nugget in Las Vegas with a total worth of $16 million. In 1984 Sinatra collaborated with Quincy Jones again for his 1984 album L.A. Is My Lady, which was well received.

Sinatra kept on performing and touring around the world until the mid-1990s. After the release of the albums Duets and Duets II, Sinatra made his last public appearance on February 25th, 1995. On May 14th, 1998, Frank Sinatra died at the age of 82 in Los Angeles following a heart attack.

In closing

What do you think of Sinatra? And what about Watertown? Let me know!

This story contains an accompanying video. Click on the following link to see it: Video: Frank Sinatra’s forgotten masterpiece Watertown. The A Pop Life playlist on Spotify has been updated as well.


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    • Edward on 03/17/2020 at 6:30 PM
    • Reply

    Thank U Erwin for this lovely article on the equally lovely cd of Watertown. Actually, lovely isn’t the right word: marvellous is better, as is magnificent and convincing. I was also made aware of this piece of art, I think it was through a documentary on the BBC. It really is the ultimate break-up album, so one’s got to be in the right mood for it. It takes you on a journey to far away desolate places, where only music can take you. I really don’t understand why this album took such a long time to be appreciated. It is simply beautiful, a jewel in any collection.

    1. And thank you for this reply! I agree 100% with all you wrote! Thank you.

    • PAUL DEAN on 08/11/2020 at 12:51 PM
    • Reply

    A Genius of an album, amazing + brave piece of work. So happy it confused the critics , The Guvnors voice is superb. Enjoyed the track by track details here. IF You Only could only have 2 Sinatra Albums it would be this and Sinatra @ The Sands, with Count Basie ..

    1. Thank you Paul. I totally agree with both your choices!!

    • Neal Fenton on 09/11/2020 at 4:09 PM
    • Reply

    Hi, I just read your wonderful historical breakdown of this deeply affecting album. I’m listening on Spotify as I write this. Last year I picked up a copy on vinyl at a neighborhood garage sale for $1.00 (!). Save for a slight mildewy smell, it is mint. Shortly thereafter, I stopped into a an estate sale in a modest home, and I picked up fifteen original vinyl Sinatra albums. I find that my adoration for a particular album varies based upon my mood and/or state of mind.

    Watertown is a tough listen. Hauntingly beautiful. Deeply sad, yet one can’t help but be drawn to his penetrating vulnerability. It is one of those albums that, as much as I try, I cannot get the casual Sinatra listener to listen to.

    What I am most amazed by is his commitment. There is nary a false moment on the album. Yes, it strange to hear his voice mixed amidst some of the somewhat dated instrumentation, but he is so honest, it rises above the subtle campiness.

    Again, it is a tough listen but certainly, when I’m in the mood, well worth the listen. Did I mention that the album cover is beautiful and that the aged vinyl still sounds revelatory?

    Again, thank you for taking the time to share such a thorough and obviously heart felt appreciation.


    1. Hi Neal, Thank you so much for your kind words. I can do nothing else than relate to what you’re saying. It’s a hauntingly beautiful and sad album, but it moves me to my core. Stunning!. Thank you so much for taking your time to comment, it’s greatly appreciated, more then you’ll probably realize. Thank you. Erwin

  1. I am a fan of all phases of Sinatra’s long and complicated career and this album stands toe-to-toe with his best work. I understand why it wasn’t successful in the same way I understand why the Beach Boys masterpiece “Sunflower” was a commercial flop. Artists get typecast and their audiences are constantly evolving. Thankfully, “Watertown” is finally being recognized for what it is — great songs given a sensitive, honest interpretation. Thanks for your blog article.

    1. You’re more than welcome. Thank you so much for replying!

    • Steven Kalka on 04/18/2022 at 3:24 AM
    • Reply

    I presently have a public library borrowed copy of Watertown. Yes, I agree it’s a masterpiece. The songs were very sad, yet so beautiful and heartfelt. I heard about the album years ago, but never listened to it until now. Two months a go I borrowed the Four Seasons based musical Jersey Boys on DVD. That lead me to listen and research their psychedelic LP The Genuine Imitation Life Gazette. After reading how Frank Sinatra was so impressed by it, he involved Four Seasons members in the production, arranging, and composing of Watertown.

    1. Thanks for the reply. It truly is a magnificent record.

    • Bob Grabowski on 04/20/2022 at 8:17 PM
    • Reply

    In the late 60s while in college, I developed a friendship with Don Alcorn, a disc jockey at WHFI FM radio in the Detroit area. He created an hour called,”For lovers and Losers.” He would read poetry and play happy and sad love songs. I recall hearing “The Train” from the Watertown Album in the early 1970s. He would also play a few of the other cuts. I purchased the vinyl which I still have and cherish and also many years ago acquired the CD. The Album Watertown has always evoked deep emotion within. I find it beautifully poetic and moving story. I often thought of it as a movie in music. It remains one of my most favorite albums. A beautiful but tragic love story.

    1. Hi Bob, thank you so much for this story. I was four years old when this album was released, but I can say I have made up that time lost with this stunningly beautiful record!

    • Doc Wallace on 05/28/2022 at 7:27 PM
    • Reply

    “Watertown” is my favorite all-time album of Frank’s. Prediction: In time, the album will rise in popularity to be among his very best work! What is “then” will become “now.”

    1. I agree, it will probably be re-evaluated 😉

    • Kathleen D Hunt on 06/14/2022 at 2:28 AM
    • Reply

    I so agree with you. This is one of my favorite albums of all time. Right up there with Kind of Blue by Miles Davis, Sketches of Spain find Miles Davis, and the song Take Me To Church by Hozier. I guess I’m just a sentimental listener (and liver),

    1. Long live the sentimental listeners! Thank you so much for your reply.

    • Valerie Scordo on 06/30/2022 at 10:29 PM
    • Reply

    I listened to the complete album of Watertown. I thought it was fabulous. I feel it was one of his better moments.

    1. 100% agreed, obviously 😉

Compliments/remarks? Yes, please!