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Memories of a Sinatra Watershed

Songwriter/producer Bob Gaudio looks back at 1970’s Watertown

Frank Sinatra in 1969
Frank Sinatra in 1969 (photo courtesy of Frank Sinatra Enterprises)

The Frank Sinatra of 1969 was a different man from the bobby-sox days of “The Voice,” the 1950s Capitol Records peak, and even the Rat Packer of a mere six years prior. Coming off 1968’s big-band session with Duke Ellington (Francis A. & Edward K.), the oddly folk music-filled Cycles (1968), the odder-still contempo pop of My Way, and the strangely poetic A Man Alone: The Words and Music of McKuen, he was uncertain where to go next stylistically.

In the mind of songwriter, producer, and Four Seasons member Bob Gaudio, Sinatra’s next stop should be Watertown, an elegiac love story/concept album/set of soliloquies about a man facing the loss of a wife—on her terms, not his. Radical in its rethinking of the male ego’s frailties (though Sinatra was considered something of a playboy, he had lived through deep heartache with the dissolution of three marriages by 1969), Watertown was produced and written by Gaudio with lyricist Jake Holmes and became the only album that Sinatra voiced over pre-recorded orchestral tracks. And though it sank like a stone when it was released in 1970, it has since become a cult classic. A 2022 vinyl re-release was remastered from the original Reprise session tapes, and the CD version includes alternate takes and Sinatra’s Billie Holiday tribute “Lady Day.”

Happy to never have a specific songwriting signature (“One of the most fun things for me is feeling confident in almost any style of music that I’d been asked to produce or write”), Gaudio states that the difference between Watertown and, say, “Sherry” or “Short Shorts” is their presentation of his diversity. “I get antsy having to follow up something I just made,” he says. A great example of that, circa 1969, was transitioning his Four Seasons—famously fronted by Frankie Valli—from doo-wop-based pop into the sociopolitical psychedelia of The Genuine Imitation Life Gazette album with lyrics by Gaudio’s then-new friend, Jake Holmes. 

“Though our album wasn’t successful, Frankie loved stretching out and had a broad range of tastes—jazz and Little Jimmy Scott, for example—and mentioned Genuine Imitation Life to his friend Frank,” Gaudio says (that would be Sinatra). “Frankie suggested to Sinatra that he should let me write songs for him. So I did. And coming off of that collaboration with Jake, I wanted to do something that Frank had never done.” 


To Gaudio, that meant something conceptual, a rock opera without the rock, that the songwriters never expected Sinatra to buy as an entire work. “Until he actually did,” says a still-surprised Gaudio. “We assumed that Frank might take two, maybe three songs. But he did it as it was, in the same form with basically the same arrangements. ‘Don’t change a thing,’ he said to me. When I asked him the exploding-bomb question about cutting the tracks with him present, as inspiration, but giving me the time to fix things, he asked, ‘Not live?’ And he said, ‘Yeah, okay, let’s do it.’ Frank was obviously open to doing something different, so we had to do something even more different, really key into his vulnerability.”

Gaudio didn’t usually tailor songs for specific artists, but Sinatra was an exception: “I was cognizant of his range, the keys and so forth, and I wasn’t far from the mark when we began recording. And each of us was looking for a breath of fresh air as to how we usually worked.

“He was Frank, yet on Watertown, he wasn’t FRANK,” Gaudio stresses. “Sinatra was always into lyrics. He could read a song without singing its melody and bring you to tears. On Watertown, he did just that, but on lyrics that weren’t his usual. Jake and I were thrilled. The vulnerability of a Vietnam War hero who had come back to his hometown, left by his wife, and left alone with his children—at that time, this was pretty unusual fare. Maybe another artist could have sung this album, but I wouldn’t know where to find them. Sinatra just broke your heart.”


World on a String: Sinatra @ 100