Song of the Day #1,158: ‘Watertown’ – Frank Sinatra

Last November I dedicated a theme week to an entire album for the first time. That was Ben Folds Five’s self-titled debut. Over the next two weeks I’m doing the same thing, with a very different record: Frank Sinatra’s Watertown.

Watertown was released in 1970 to tepid sales and lukewarm critical reception. It probably doesn’t show up on most lists of Sinatra’s best albums, regarded more as a curiosity than an essential recording.

But this tear-soaked concept album is both a touchstone of my childhood and one of my favorite Sinatra records. I’ll be thrilled if I can give it some much-deserved exposure (no matter how little) through my blog.

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Song of the Day #4,567: ‘April Come She Will (Demo)’ – Paul Simon

In recent months, I’ve found myself declaring a couple of times that one song or another was officially among my all-time favorites.

That got me interested, during these pandemic times, in creating a definitive playlist of my favorite songs. This is an exercise fraught with peril and subject to repeated second-guessing, but that’s also what makes it fun.

Narrowing such a list to ten songs proved impossible, so I kept at it until I had close to 30, then pared back to 25, which feels like a good number.

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Song of the Day #3,217: ‘I Know Him Too’ – Tift Merritt vs. Frank Sinatra

Our next match-up in Round One of Montauk Madness pits the legendary Frank Sinatra against the tragically under-appreciated singer-songwriter Tift Merritt. A no-brainer, right? I agree… Tift Merritt advances.

Sinatra acolytes (like my parents) will scoff at this choice, I’m sure. But as much as I love Sinatra’s voice, and his interpretation of classic songs on such albums as Only the Lonely, Songs For Swingin’ Lovers, In the Wee Small Hours and Watertown, I find it hard to vote for a non-songwriter over an excellent and prolific one.

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Song of the Day #2,822: ‘Box of Rain’ – Grateful Dead

american_beautyWhen compiling my list of favorite 1970 albums, I was tempted to include Grateful Dead’s American Beauty. Every time I listen to this record I’m reminded just how great it is.

The problem is, I almost never listen to it. Maybe three times in the last decade. Granted, I don’t pull out Let It Be or Watertown on a weekly basis either, but I know both of those albums by heart because I did give them that level of attention at some point. American Beauty never earned its own obsessive phase.

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Song of the Day #2,817: ‘Lady Day’ – Frank Sinatra

watertown_sinatraMy second favorite album of 1970 is Frank Sinatra’s little-known but no less classic concept album Watertown.

The album tells the tale of a man picking up the pieces after being left by his wife. He raises his two children, earns the sympathy of his neighbors, and quietly tries to win her back. The record ends with him waiting in the rain at a train station, the wife having gone back on her promise to return.

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