No one under the age of fifty really listens to Frank Sinatra anymore. Like anything else, there may be exceptions to this fact, but overall it’s true. Frank Sinatra is a legendary artist whose work will always be enjoyed and referred to. However, his era of direct relevancy is obviously long gone, and his era of anecdotal relevancy is starting to fade.

We associate Frank Sinatra with a bygone era of America, a time of guys and dolls, a time when people would swing and dance and when the lounge singer was king. Sinatra’s unique talent was maintaining this vision even as it eroded away over time—to make you feel old-fashioned feelings in a modern era. Sinatra’s heyday was from the late forties to the late fifties, yet he recorded “New York, New York” in 1977.  And “My Way” makes you feel like a proud man looking over the skyline of post–World War II Manhattan, even in 2013.

Still, Sinatra’s most overlooked achievement is perhaps the one album he made that did not feel as though it was evoking the era he loved or knew the most. In 1969, the same year that Frank Sinatra recorded “My Way,” he released an album called Watertown. Chances are, even some of the biggest Sinatra fans—like my grandparents and great aunts and uncles—have forgotten about Watertown. But Watertown is Frank Sinatra’s best album and his most enduring contribution to American culture.

If you listen to enough music and read enough music criticism, you will often find album reviews that liken a song to a short story or an album to a novel. We want our music to take on serious importance, to assume the stature of the highest literature. I’ve listened to a lot of albums, and besides Van Morrison’s Astral Weeks, Frank Sinatra’s Watertown is the only record I can honestly say feels like literature on record.

The album is ostensibly about a man who lives in Watertown, which is supposed to be Anytown, U.S.A.; a place where “nothing happens down on Main / ’cept a little rain.” This man has lost a woman, a woman who we presume to be his wife. He may have lost her due to a painful divorce, or she may have died—we don’t know.

That’s it, though. That’s the concept of the entire album. Along the way, we have ruminations about the protagonist’s children and which parent they look like; the fact that he won’t get over his significant other for a while; and that no matter what, if he knew then what he knows now, he’d still be in love anyway. Finally, the album ends with the protagonist waiting for a train to pull into Watertown that is supposed to be carrying his significant other back into his life—whether this is imagined or not is unclear. While the protagonist waits, he explains to his significant other all of the changes that have happened while she’s been away and how much there is to say to her; how they will walk down the street and look very much in love on their way to getting the kids from school. Yet, when the train comes, he doesn’t see his significant other anywhere.

That’s the album; that’s what Watertown is “about.” The story is ambiguous, but it is constructed very much in the tradition of any realist or, hell, even modernist literature. We listen as the protagonist narrates the smallest details of his life, his daily routines, his smallest epiphanies, all in an effort at getting over his wife who is either dead or has left him. Watertown is made of the same stuff as Flaubert, Woolf, Hemingway, Joyce, Faulkner, and Tolstoy. All those writers who drove so deeply into reality that they could do nothing but heighten it.

Now, take a step back and remember one thing: we’re talking about Frank Sinatra. A Frank Sinatra record made at the edge of the 1970s. Since Watertown is an album and not a book, and since Frank Sinatra is a singer and not a writer, we clearly have to discuss the music itself.

When you think of Frank Sinatra’s music, you probably think of swelling string arrangements, brassy horn sections and tinkling, out-of-reach piano notes. And, of course, there is the voice, that irrepressible instrument of confidence and composure. It is the kind of music that is married to cocktails and tastefully lit dining rooms and bars; it is the music that any American born after 1950 has had naturally embedded somewhere in their blood and consciousness.

But that’s not the Sinatra on Watertown. There are still string arrangements all over the album and little bits of brass where things get triumphant, though triumph on this album is nothing more than the sound of complete and open longing, those moments when you remember some previously forgotten walk under the tress on your college campus on a beautiful day and realize that you can never recapture the vibrancy of even a forgettable moment of youth. But overall, it is very much a Sinatra you have never heard before. There is electric bass directly from the brains of McCartney or Wilson; melodies that seems oddly Hendrixian; and pianos and melodies that you can even imagine early Bowie singing.

The album opens with the ominous, round bass notes of the title track. Sinatra enters the mix and he sings in a tone of not so much insecurity, but the tone of a man who seems defeated—or at least resigned to the fate that he’s been given. It’s a jarring tone, but as a listener, it intrigues you and draws you in for the ups and downs of the rest of the album.

And it would be easy for me to discuss each song at length; I could tell you why “Elizabeth” is a lost song from Pet Sounds; how “Goodbye (She Quietly Says)” might be the saddest song of all time; and how Jimi Hendrix, had he lived, would have one day covered “What’s Now is Now” in his inevitable “mellow” phase that would have began in 1973 and ended once he heard Marquee Moon. However, that would just be exhaustive.

There is one stretch of songs I do want to discuss, though. In my opinion, the heart of Watertown lies in the songs “For a While,” “Michael & Peter,” and “I Would Be in Love Anyway,” the third, fourth, and fifth songs of the album. Over the course of those three songs, you experience the gamut of emotions that the entire album covers, but in just the right doses.

“For a While” is a fluid ballad filled with plucked guitars, rattling marimbas, nimble bass, and the requisite Sinatra wood and string sections. To me, it is the sound of the month of April. (And I recommend listening to “For a While” some spring morning on your way to work and dare you to disagree.) But at the heart of this song is a tremendous sense of loss. A lyrical example:

People say to me
You need company
When you have some time to spend
Drop around and meet a friend
They forget, that I’m not over you
For a while.

Those lyrics, cowritten by Jake Holmes (who wrote the original version of “Dazed and Confused”) and Bob Gaudio (former member of the Four Seasons) are concise and perfect. They need no extrapolation.

Going from the third song to the fifth song, “I Would Be in Love” is the best example of the album’s “doing” triumph. The song opens with nearly-chiming guitars, piping woodwinds, and Motown piano as Sinatra sings:

If I knew that you would leave me
If I knew you wouldn’t stay
I would be in love anyway

Sometimes I think, I think about before
Sometimes I think

Then, the music soars all together and Frank belts it out in his biggest “My Way” voice:

If I knew then, what I know now
I don’t believe I’d ever change somehow

Again, you don’t need someone to explain those lyrics to you. The music feels triumphant and it carries you, but the actual “triumph” is just a tiny epiphany, one man’s realization that he’d never change—no matter what.

Finally, skipping back up to track number four, there is “Michael & Peter,” which is one of the lost masterpieces of sixties pop. This song covers nearly every complex tone and emotion you can imagine. It begins with lilting, almost Spanish guitar, as the protagonist sings about whose faces each of his kids have and how his son Peter looks like him, “except when he smiles.” Then, the track switches after about a minute to a slightly haunting but driving piano melody where the protagonist explains how much rain the town has gotten and other day-to-day minutiae, such as the house needing a new coat of paint.

And after about another minute, the tempo goes up a gear and an Ennio Morricone guitar and a xylophone come in. The protagonist sings about working “for Sante Fe” and how he has never skipped a single day and the entire songs feels extremely inspiring. When you finally reach what I suppose is the actual chorus, there are sweeping strings and staccato horns and the protagonist is singing, “as far as anyone can tell, the sun will rise tomorrow.” The whole thing repeats again and then fades out as the protagonist repeats, “you’ll never believe how much they’re growing.” I don’t need to say anything.

People still enjoy the music of Beethoven and Mozart, but their immediacy has long since faded. The same thing will happen for the majority of Frank Sinatra’s music as we move on through the twenty-first century and into the twenty-second. “The Way You Look Tonight,” “I’ve Got the World on a String,” “Fly Me to the Moon,” those songs will all be recognized as great and important, but we won’t feel them as much in our daily lives, feel their relevance. They won’t matter as anything more than distant documents of where our culture was at one point in the twentieth century.

The Beatles and Bob Dylan will forever be relevant because they were able to link our heads and our hearts in the strangest ways; and the Rolling Stones and Led Zeppelin will remain inescapable simply for what they do to our guts and how they make our blood and muscles feel with just the smallest guitar riff. However, a lot will fall by the wayside. I don’t mean to simply wave the flag of  classic rock, but the conversation has to be reigned in.

Though the more I listen to Watertown, the more I think it is Frank Sinatra’s one chance to be truly felt by listeners hundreds of years from now. To me, the album sounds out of time. When you listen to Watertown, you don’t picture Manhattan in its heyday after America’s triumph in World War II; you picture a guy walking aimlessly around his house in a town that could be in America or Ireland or rural France; you picture a man looking at old photos and watching the dust drift above his carpet in the fading, orange light of a Sunday afternoon. And even if the music iteself doesn’t pass your test of timelessness, the lyrics and the story do. Divorce, death, loneliness, and growing older never go out of style. Those underlying elements of everyday life and the epiphanies that come along with them have been relevant from Shakespeare to Tolstoy to Joyce to Louis C.K. Watertown was the one time Frank Sinatra wasn’t singing about emotions that seemed as though they could be bought in a box. It was the moment that the man who sang “My Way” realized that pride and love and pain all come in subtler forms and shades.

Matt Domino loves the NBA and writes fiction in Brooklyn. His writing has appeared in various places and he runs a blog called Puddles of Myself.