Frank Sinatra always recorded his vocals the same way. He would stand at the mic in the center of the room, surrounded by a large ensemble, conducted by an arranger who’d written the score to suit Sinatra’s own voice and mood. In the 1940s and ’50s, his baritone emerged in slow, steady sweeps, reaching out and reeling you in. He sang about universal topics with such ease and charisma, attracting such a large audience and developing such a recognizable persona, that his role in the greater cultural consciousness now lands somewhere between myth and a cliché. But back then, it was based on these particular choices, tailored to the voice, the sound in his head and the story in the words.
If those predilections seemed out of fashion in the ’60s—when artists were moving away from singing the standards toward writing their own compositions, backed by music that jittered and quaked as opposed to swooning and swinging—Sinatra found a way to reposition himself. It was during this decade he began operating his own record label Reprise—where he assumed the enduring nickname “Chairman of the Board”— and bolstering his acting bona fides in films like The Manchurian Candidate and The Detective. This was also around the time he took up residency at the Sands Casino in Las Vegas, where he gathered with crowds of like-minded performers and celebrities and refitted his music for an older audience, solidifying the image he would maintain in pop culture for the rest of time. “How did all these people get in my room?” he would ask the crowd at the start of sets at his casino sets. More than half a century later, it can feel like we never left.
During the ’60s, Sinatra’s voice also began showing some wear—a little gravel at the end of a line, longer pauses between the words. This raggedness allowed his best performances to tell a different kind of story. “Now I think of my life as vintage wine from fine old kegs/From the brim to the dregs,” he sings as strings swell in his 1965 rendition of “It Was a Very Good Year,” a song whose lyrical conceit (“When I was 35…”) demands a performer at least capable of portraying a man with as much life behind as ahead. The wear and tear of Jack Daniels and unfiltered Camels and years of public agonies and stress all build toward a slightly wearied, self-preserving effect, pulling him back like concerned friends in the places he might have once caused a scene. But the drama is still there. Listen with your eyes closed, whether you know anything about Sinatra or not, and you can see him—the slender guy in a suit, cigarette in hand, shoulders swinging. Listen closer and the room fills up—the elbows of the orchestra swaying like waves, stage lights dimming as the audience applauds.
But who is the man on Watertown? By Sinatra’s standards—and by most standards—this was a strange project. It was the first of his records to feature all new compositions, written specifically for him. Moreover, it was a concept album. It was also the first time he overdubbed vocals separate from the music, tracked in isolation in a Los Angeles studio, in part because he was unhappy with his initial performances, in part to avoid being on the East Coast during an investigation into certain organized crime operations, and in part to meet the current standard of studio recordings as the ’60s drew to a close.
Sinatra’s career was, if not failing, then at least growing stagnant as the times changed. He was not a fan of rock music, and he even had taken to referring to the new generation of artists as “pukes.” To his credit, he still experimented. There was a brief, beautiful record with bossa nova guitarist Antônio Carlos Jobim. There was also a collection of poetry by trendy writer Rod McKuen set to music. He was trying new things, pushing himself out of the box.
This perhaps led him to the set of a dreadful Western called Dirty Dingus Magee, a box office flop that would prove to be his last film role for many years. By all accounts, it should have at least been an interesting failure. Sinatra—whose best performances were not far from his dignified public persona—playing a guy named Dirty Dingus Magee, a goofball outlaw, the butt of everyone’s jokes, scruffy and desperate and quick to make a self-deprecating joke. Novelist Joseph Heller contributed to the screenplay, and an organization called the IFTP (Indians for Truthful Portrayal) somehow offered their first endorsement for a Hollywood movie’s representation of Native American characters. (Roger Ebert, in a one-star review, notes that the IFTP’s president “talks amazingly like an MGM press agent.”)
The filming of Dingus took place just after Sinatra’s father, Antonino Martino “Marty” Sinatra, died of a heart attack. By this point, Sinatra had been divorced three times; he had killed and kickstarted his career enough times to feel like a ghost of himself; he had lost friends and collaborators, seen trends come and go. Due to an injury incurred on the set of 1962’s The Manchurian Candidate, the hand he used to hold a microphone was often in immense pain. But his father’s death, according to those who knew him, was what broke him. “He became a little more quiet, a little less ebullient,” his daughter Tina reflects in My Father’s Daughter: A Memoir. “He needed this silliness after Grandpa died,” Nancy Sinatra Jr. explained. After Watertown arrived to the worst sales of his career in March 1971, and after Dingus hit theaters to critical disdain that fall, he announced his retirement, and, for a short while, disappeared.
The story of Watertown goes like this: A man is left alone with his two sons after his wife, Elizabeth, leaves for the big city. He feels lonely, hopeless, lovesick, and bored. On a sunny day, he goes to the train station, hoping she will return. She does not. Then it rains. The End.
The songwriters, Bob Gaudio and Jake Holmes, wrote all 10 songs with the ambition of stripping Sinatra of everything that had come to define his music, as if dictated by a series of prompts.
Where do Frank Sinatra songs usually take place? Somewhere luxurious and exciting, or if the mood strikes, a smoky bar, filled with familiar faces and commiserating drinkers. Watertown is set in a small town that may or may not be the one in upstate New York, some 30 miles from the Canadian border. “Nothing much happening down on Main,” Sinatra sings in the opening title track. “’Cept a little rain.”
Who is the usual narrator of Sinatra songs? It is a man in touch with his feelings, able to express himself with great passion and conviction, communicating even his lowest thoughts with the composure to suggest he’s on his way to better things—or at least a nicer bar. On Watertown, our narrator is nameless and listless, dwelling neither in pain nor in anger, circling the same subject over and over as the days blur together. “As far as anyone can tell,” he sings in what may be the album’s most hopeful line, “The sun will rise tomorrow.”
What do breakups usually sound like in Sinatra songs? They are elaborate, catastrophic events, narratives that demand to be orchestrated with the grand opulence of Christmas songs and film scores. On Watertown, the central breakup is a cold, empty thing that onlookers might ignore entirely if we didn’t have access to the protagonist’s internal monologue. “There is no string ensemble,” he tells us, “And she doesn’t even cry.”
These are, on the whole, the sparsest and saddest songs that Sinatra ever sang. The big swing for a single was “I Would Be in Love (Anyway),” which arrives early in the album to declare that this marriage was the peak of the narrator’s life, no matter how poorly it turned out. The second-to-last track, “She Said,” goes down in less than two minutes, consisting almost entirely of brief messages from Elizabeth, sung slowly and sternly over strange, clattering percussion and brief flourishes of strings. “She says she’s coming home,” it concludes. By the next song, you realize this was either a hallucination, a lie, or a cruel joke.
When Sinatra and his team enlisted Bob Gaudio for the project, it’s likely they were thinking about the hits that he wrote for the Four Seasons—pop morsels like “Sherry” and “Big Girls Don’t Cry,” songs that share Sinatra’s penchant for romance and humor and swingin’ melodies. Or maybe he was thinking about the hits he co-wrote for other artists, like the Walker Brothers’ “The Sun Ain’t Gonna Shine Anymore,” a mini-opera that captured heartbreak at its eternal, elemental peak.
Instead, they got the Gaudio who had just come off The Genuine Imitation Life Gazette, the Four Seasons’ bizarre and fascinating 1969 concept album, inspired by recent innovations like Sgt. Pepper’s Lonely Hearts Club Band. The album, which blended political satire with long-form symphonic song structures, was a failure, and it seems that Gaudio and his writing partner, Jake Holmes, learned a lesson to rein in their ambition this time around. The Watertown tracklist is brief; the mood is focused; the color palette is muted and sepia-toned. The songs don’t necessarily follow a linear narrative, but if you were to cut any of them, or listen in a slightly different order, it would ruin the effect.
Maybe it could have been a success. There’s a “Mrs. Robinson” jaunt to “The Train,” and a lonesome Glen Campbell twang to “What’s Now Is Now.” The magnificent, waltz-time chorus of “For a While”—“I forget that I’m not over you… for a while”—has a baroque charm, accompanied by French horns, muted piano, and gentle strums of acoustic guitar. “What a Funny Girl (You Used to Be),” with its memories of messy kitchens and tableaus of teddy bears, cuts through with much-needed lightness at just the right time. “Elizabeth” kicks off with an actual electric guitar solo. It’s all pretty hip, in an AM-radio-soft-rock-circa-1970 kind of way.
But then there’s Sinatra. With the disembodied effect that comes from a guy singing alone who’s used to singing with bands, his vocals elevate Watertown from merely a well-crafted left-turn into a downer classic. He’d sounded more polished before, and he would sound more confident later, but he never reached quite the same emotional tenor for the span of an entire record. No singer ever has sung the word “goodbye” quite like Sinatra, and here, he gets another song devoted entirely to it: “Goodbye (She Quietly Says)” is the only track on the record that involves both characters in a room together and it’s narrated in the past-tense, a descending chord putting its vision further in the rearview with each repetition of the chorus; the effect is so haunting and dejected that, placed so early in the record, it feels like an attempt to clear any casual listeners out of the room.
It’s the kind of casual inside joke shared among people who’ve cohabitated for a long time, and in this telling, Sinatra exudes equal resentment and sympathy for the guy. You get the sense that what might have once been an annoying routine between the two has now become a kind of comfort: At least he has some company, and at least he gets to talk about her again. You see him hunched over the letter, underlining each word, laughing to himself a little, writing more quickly as he loses himself to the memory. It is maybe at this precise moment, delivered at the end of the final verse, that the narrator decides not to send the letter.
None of this, for what it’s worth, is in the lyrics. It’s all how Sinatra sings it, stringing the words together, taking a deep breath and lowering his voice, maybe even doubting himself a little as he summons the bravado to sing what might be the most banal observation ever to find itself at the climax of a Frank Sinatra song. And if he used to give these types of performances in banquet halls filled with musicians and friends, electric and buzzing with live music, in this telling, he takes off his headphones, exits the recording booth, and stands in a soundproof room somewhere in Los Angeles, at the precipice of even more quiet to come.
Frank Sinatra announced his retirement in March 1971, and he was back on stage and making records again by January 1974. But even before his self-induced exile from the industry, it never seemed like Watertown would play much of a role in his narrative. Just a few months after its release, during a radio interview, he seemed to have forgotten the names of the songwriters he worked with (“I think the two kids did a great job”), and rumors quickly died about a TV special where he’d play the lead. It’s hard to imagine what this would have even looked like: a guy sitting alone in his house, singing to himself while gazing wistfully out the window? A scene-stealing appearance from the old man cutting the lawn? In the context of the career-spanning 2015 documentary, Sinatra: All or Nothing At All, Watertown accounts for roughly 20 seconds of its four-hour runtime, all in the service of explaining how dire his commercial prospects were before retiring.
The only song from the sessions that ever made it into Sinatra’s concert setlists was “Lady Day,” a gentle, non-album single that seemed to have nothing to do with the larger concept. Sinatra would introduce the song as a tribute to Billie Holiday, who had died from liver damage about 10 years earlier. Even with its elegiac tone, the words are sweeter and softer than anything on the record. “Her morning came too fast, too soon,” Sinatra sings, “and died before the afternoon.” It’s sad, but, in his telling, it also sounds a little like relief.
A common line on Sinatra is that he could not sing what he did not feel, which, like a lot of inherited wisdom about Sinatra, seems to be about half-true. After all, he’s on record as having never enjoyed performing chestnuts like “Strangers in the Night” or “My Way,” and throughout the ’70s and ’80s, he recorded plenty of ill-fitting material that might have seemed like a stretch, even then—say, “Sweet Caroline” or “Just the Way You Are.”
When Gaudio and Holmes sent Sinatra their homemade demos of the material (“Who has the nerve, at 28 years old, to sing a demo for Frank Sinatra when you’re not a singer?” Gaudio reflected earlier this year), they were under the impression he would pick just a song or two. Instead, he was taken by the whole project. Maybe it was the recent death of his father and the songs’ sympathetic portrayal of parenthood from a man’s perspective. Maybe it was its depiction of a woman leaving her marriage to pursue life in the big city, as he had recently served Mia Farrow divorce papers while she was in Los Angeles on the set for Rosemary’s Baby. (Sinatra had demanded Farrow—his wife of two years, almost 30 years his junior—abandon the project and meet him in New York, where she would co-star in his own film, The Detective. “While she’s working for us, she’s Mia Farrow, not Mrs. Sinatra,” he was reportedly told by a producer. This was the last straw.)
In the decades to come, Sinatra had more hits ahead of him. His rendition of “New York, New York,” released in 1980, would finally replace “My Way” as the crowd-pleasing closer of his live sets. He’d also return to his saloon ballad comfort zone on 1981’s She Shot Me Down, reuniting for the last time with arranger Gordon Jenkins to follow the thread of his more characteristic breakup songs from the ’50s and ’60s. He even returned to film work, some seven years after Dirty Dingus. Which all leaves Watertown in a vulnerable position, documenting an artist at a personal low, released to widespread indifference, clearing the path for the first moment in a long career where he felt that nothing of any consequence lay ahead of him.
There is some irony in this set of songs—written specifically to avoid the common tropes of Sinatra’s image, already set in stone by 1970—aligning so closely with his personal life at the time. But any autobiographical symmetry dissolves when the music plays. Unlike “Lady Day,” which Sinatra could perform as his own remembrance of a lost colleague, there was no way to fold these songs into his greater body of work. A charming gentleman in an expensive tuxedo does not sing “Goodbye (She Quietly Says).” “Michael & Peter” would not make sense for the audience at a casino. Try telling the narrator of “For a While” that the best is yet to come. These songs stand apart, and so Sinatra kept them apart. In their words—full of anticlimaxes and dead-ends, solitude and longing, small towns and gray skies, empty trains and unsent letters—there was a story close to his heart, one as serious as life and death. It wasn’t the story he’d set out to tell, or the one the world wanted to hear from him. But it was the story, nonetheless.