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‘Watertown’: Frank Sinatra’s Overlooked Masterpiece

An ambitious concept album about an imaginary town, Frank Sinatra’s ‘Watertown’ is one of his least-known albums, but remains a high-water mark in his career.

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When this album was originally released it was not one of Frank Sinatra’s best sellers, even now it is one of the lesser known of Sinatra’s album. Yet it shouldn’t be as it is an absolute masterpiece.

If A Man Alone, Sinatra’s 1969 album, was ambitious and different, then Frank clearly thought it was a trend worth continuing the following year with Watertown. Where his classic Capitol albums were thematic, this is a concept, in reality a song cycle, play, story, about an imaginary New England town. Bob Gaudio and Jake Holmes created this tale of a man who has been left by his wife to look after their children. Each song adds to the imagery and at the same time conveys the sadness of a man without hope.

Sinatra handles it brilliantly and conductor/arranger Charlie Calello creates a musical backdrop that is both retro and modern, a perfect counterpoint to Frank. It is a brilliant, underrated album and amongst serious Sinatraphiles it causes tempers to fray in heated debate as to its true merits. It became Sinatra’s third album in succession to do better in Britain than America. One aspect of Watertown’s failure was its lack of obvious single material. As a concept album it was very definitely the sum of its parts.

Watertown can be bought here.



  1. Robert clatworthy

    August 29, 2015 at 2:11 pm

    Is it available as a cd?

    • Jack G

      August 29, 2015 at 8:04 pm

      It is available as a CD and it includes a bonus track called Lady Day, with a different arrangement from the one on the Sinatra and Company CD. I love the Watertown album, so completely unlike any other Sinatra music. It tells a heartbreaking story and all the songs are connected.

  2. Marie

    August 29, 2015 at 11:31 pm

    I have this for a couple of years it is on cd.

  3. MarcH

    August 30, 2015 at 6:05 am

    How do you know the song refers to Watertown, MA rather than to Watertown, NY? BTW, I’m not sure either of them ever had a long distance train station..

  4. Donald

    October 7, 2015 at 9:12 am

    This cd makes me cry… It’sso emotional…

  5. Gerald Samociuk

    December 13, 2015 at 9:06 am

    I only discovered this album, this year and it is a real hidden gem. As part of the centenary the vinyl is available but I bought the cd as it was a bit of a gamble, not regretted it, although my version does not have the bonus of Lady Day on it, so there must be at least two versions.

  6. James smethurst

    September 5, 2017 at 3:01 pm

    Unusual album. In retrospect highly recommended
    Not the usual Sinatra. A more introverted feel. Similarl though not reaching the heights of In the wee small hours.Nevertheless a fine album.

    • James smethurst

      February 10, 2018 at 7:45 pm


  7. Christopher Matson

    March 30, 2019 at 9:29 am

    This album reminds me of Scott Walker 4 and the Richard Harris albums with Jimmy Webb.

    For me those are flattering comparisons.

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