Sinatra’s Master Class, and the Bleak Genius of ‘Watertown’


(Photo: Sinatra)

When a vocalist steps on stage, this is the least and the most we can expect of them: they should sing each song as if every word, every syllable, was a story coming straight from their heart to yours; they should sing each song as if it had never existed before that day, that moment. Each song should be an ecstatic conversation between artist and listener.

On his 100th birthday, we celebrate the incomparable Frank Sinatra.

Frank Sinatra was almost 76 years old when I saw him at Nassau Coliseum on November 5, 1991. On that evening, he sang as if every hiccup of the heart and every twist of fate in the songs he sang were occurring to him for the very first time. He sang as if his career, as if everything we would ever think about him, depended on what we would see (and see him feel) this evening.

I had seen other artists perform like this—I have watched everyone from Axl Rose to Paul Weller play sets where they seemingly wanted to convince everyone watching that the seal of their heart had opened up at that very moment, only for them. But here was Sinatra, one of the most famous men of his century, a man with so little to prove that it seemed like a miracle that he was even standing in front of me, performing as if there was nothing as important as the words he had to sing in that room on that night. That evening set a standard for every live performance I would ever see again.

Although I have enormous affection for Sinatra’s recordings and a deep fascination with the shadow he cast against the backdrop of his time, on that evening in 1991 nothing else mattered but the miracle of emotion, intention and communication he displayed. It was a Master Class in the most important thing a musician should know: Whether you are the most famous artist on earth performing in an arena or a teenager playing fifth on the bill at some DIY hardcore show in a crappy part of town, the majority of people watching you have never seen you before. You must play your set as if this is the one and only chance you will ever get to make the listener a fan for life. You must convince that listener that they should be a partner in your dream. You have one chance. You will very, very likely never have that chance again.

Sinatra played that night as if it was his one chance.


For Frank Sinatra’s 100th birthday, I also want to celebrate one of his most remarkable albums. 1970’s Watertown is virtually the definition of “little-known concept album.” It was one of Sinatra’s poorest selling albums—it may be the poorest selling Sinatra studio album—and until very recently it had been long out of print. Considering that it contains no trademark Sinatra songs and the album is about as cheerful as watching a group of children in a cancer ward do a performance of Requiem For a Dream, Watertown’s obscurity probably isn’t that surprising.

It made some sense that Sinatra would attempt a story-driven concept album, considering he had helped pioneer the thematic concept LP in the 1950s. But on Watertown Sinatra did something truly risky: He told an entire album-length story from the point of view of character that is most definitely not Frank Sinatra.

Even in his darkest moments (on, say, In The Wee Small Hours), the listener is damn aware that Sinatra is still, well, Sinatra. The Scotch in the glass that reflects his tears is still 12 years old, the Marantz audio system he had installed in his lonely hotel suite is still playing Kind of Blue, and in his right front pants pocket he still absentmindedly fingers a $500 chip from the Desert Inn. We know that, for all his mourning, the doorbell will shortly ring and Tura Satana will be standing there wearing a fox fur with nothing underneath, mumbling the words “Vic Mature sent me to cheer you up.”


(Photo: Sinatra)

But on the extraordinary Watertown, Frank Sinatra is singing from a point of view that is recognizably not Frank Sinatra; he plays the role of a middle-aged working stiff who lives, loves, and loses far, far away from the Big City Lights, in a slightly on-it’s-heels heartland town. The concept of Watertown is relatively simple: A woman leaves. Kids are involved. Spoiler alert: There’s no happy ending. To quote Wikipedia at it’s most effectively dry, “…tracks 1-5 tell the story of the main character’s disbelief in his wife leaving…tracks 6-10 tell of the main character’s desperation.”

And there you have it. Sitting somewhere between Lou Reed’s Berlin and Springsteen’s Nebraska, Watertown details an ordinary life split apart and the ordinary extraordinary pain of trying to go on. The mood of the protagonist (he sounds like Sinatra, but why is he worrying about getting promoted and making small talk with the old guy who waters his lawn?) fluctuates between desperation, disappointment, optimism, memories cloaked in morbid, bittersweet tones, and resolution; mostly, he convinces us that he has lost his only chance at love, his only shot at holding his family together, the only bright spot in his dull existence. The deeply dramatic, slow-moving songs seem to belong in a world Scott Walker, Gavin Friday, or even Elliot Smith should live in, not the brash glamor we associate with the Sinatra brand name.

Watertown also features one of Sinatra’s greatest recordings, “Michael and Peter.” In the song, Sinatra considers the two children of the now-split couple, and he details how each does and doesn’t resemble their parents. He uses this as a starting point to describe how life goes on (and doesn’t go on) without his paramour (“I think the house could use some paint/you know your mother’s such a saint/she takes the boys whenever she can”), while repeating the increasingly desperate couplet, “You’ll never believe how much they’re growing.” In mood and style, “Michael and Peter” reminds me of one of Sinatra’s greatest moments—his recording of Rodger & Hammerstein’s “Soliloquy” from Carousel.


Although Watertown is occasionally rousing, these moments are deliberate red herrings, reflecting the many swings in mood and circumstance of someone who has lost their one true love.

Peculiarly, the current reissue omits the album’s epilogue, “Lady Day,” the only track where the protagonist steps outside his self-abnegation long enough to recognize that the one who left may have had dreams bigger than him and Watertown. Instead, the album now ends with the profoundly depressing “The Train,” where the excited narrator, sounding truly upbeat for the first time in 35 minutes, waits at the station for his returning love, only to find that she never comes. At this point, we want to say to Sinatra, “I’ll just leave you with this full bottle of Valium and a glass of Diet Dr. Pepper. I’m going to Friendlys. I’ll make sure your sister takes good care of the kids.”

(Some Watertown scholars have suggested that the album is about a spouse who has died. It’s certainly possible—and that idea fits the album’s sleepy, sepia melancholy—but I think it’s more likely that the wife has just left for greener pastures.)

The album was produced by Bob Gaudio, the mastermind behind the Four Seasons, and composed by Gaudio and Jake Holmes (who is, perhaps, most famous for having written the song “Dazed and Confused”). For the most part, Gaudio avoids the abstract indulgences of The Genuine Imitation Life Gazette, the remarkable concept album he had produced the year before for the Four Seasons. Whereas Life Gazette seems to be weighed down by its almost Goliathan pretensions (it sounds like Van Dyke Parks and Joe Byrd getting together to record the Moody Blues Days of Future Passed with Morton Feldman looking over their shoulders), Watertown is mostly taut and concise, offering the breadth and darkness of Life Gazette but without its nearly stupefying pretension.

If you listened to Wee Small Hours while you were in your 20s or 30s, you may have thought, “This is a great account of loss, but he shall love again.” Watertown, on the other hand, delivers the devastatingly more realistic message that life, age and class may conspire that we will never again love or dream as we once did.   

On the other hand, we will always have moments like November 5, 1991.

Sinatra’s Master Class, and the Bleak Genius of ‘Watertown’