Sinatra’s Deep, Dark, Desolate Flop. And Why It’s A Masterpiece.

This article is from our friends at Trunkworthy

Watertown is the unlikely, unexpected and, for decades, unappreciated collaboration between Frank and Four Seasons’ mastermind Bob Gaudio that cuts to the bone in grand style.

Frank Sinatra knew from dark and downcast. Just check albums like In the Wee Small Hours or tunes like “The One That Got Away” and “One for My Baby (And One More for the Road),” wherein he taps the barkeep for a couple extra shots of liquid courage before, disconsolate over a flown dame, getting in his car and driving down your street.

But Watertown, the 1970 commercial-flop album conceived and produced by Jersey Boy Bob Gaudio (an unexpected move given how much Sinatra disliked rock music), is in a whole other league. It’s a sober affair, an 11-song cycle about the dissolution of a marriage, sung from the perspective of the left-behind husband and dad (two sons: see the wrenching yet remarkably un-maudlin “Michael & Peter”). Sinatra is shattered, confused, regretful, resigned in performances that belong with his best—and here’s why it works: He does it by refusing to overplay the pain. Yeah, he’s hurt, but there’s no Nick Cave self-laceration, no Scott Walker wallowing, no equating his straits with the collapse of the cosmos. Watertown connects because the all-time song-reader never abandons the perfectly human scale of Jake Holmes’ lyrics and Gaudio’s melodies. Listen: If this record doesn’t grab you, maybe you’re Robert Stack-ing it—untouchable.

The title track sets it all up: wife decamps for the city, packing dreams, leaving Frank and the boys stuck in smallville. “Goodbye (She Quietly Says)” sketches the couple’s anti-climactic final scene. Facing each other across a coffee-shop table, he half-gallantly proposes one last try, but she’s already gone. “There is no great big ending, no sunset in the sky/ No string ensemble, she doesn’t even cry.”

It’s the small stuff that hits the heart, like the details of post-breakup life that accrue in “Michael & Peter.” Sinatra seems to shudder at the quickened, frightening sense of time passing (“The roses that we planted last fall climbed the wall”) and moves through a range of emotions as he ponders chucking much of what’s left of his life: “All those years I’ve worked for Santa Fe, never missed a single day/ Just one more without a raise in pay—and I’m leaving.”

Things, of course, don’t end well. We learn this as the verses of “The Train” unwind, full of what turns out to be Frank’s false hope of a rapprochement. And yet . . . If hard knocks left the hero of “My Way” wiser, perhaps he was also a little too prideful. Watertown’s guy learns just as much from painful experience—but emerges humbled and way more grateful. In what’s arguably the album’s high point, “I Would Be in Love (Anyway),” he’s got the guts to come out and say it: If he knew at the start it would end this way, he’d still have done what he did: loved her, made a family, believed in a future.

The arrangements, by Four Seasons vet Charlie Calello, Joe Scott, and Gaudio, are as simpatico as any Sinatra’s ever had, as sparse or orchestrally spacious as the songs call for. “I Would Be in Love (Anyway)” features a 12-string folk-rock underpinning, and piano and French horns and a stirring, Righteous Bros. build to the chorus. The strings on “Michael & Peter” slay me; so do the track’s bass-string “Wichita Lineman” guitar lines and, in spots, the Pet Sounds ambience. None of the sensitive settings would mean a thing if they weren’t surrounding these vocals by this singer on such moving compositions. Devastating loss may never have sounded so irresistible.

Maybe it’s ironic that when he recorded Watertown, Sinatra was trying to prove he could again be hip and relevant. Concept albums were the rage in those post-Pepper days, so he cut one. It stiffed. But he created something that did the job far better than the Nehru jackets, love beads, and Caesar-cut rugs: that rarity, a set of performances that, more and more, sounds timeless.