When he was in his very good years, the music came effortlessly. Or so it seemed. The voice sang true, and it was filled with emotion, with love and sorrow and jubilation. 

But in the autumn of his years, what was once nice and easy turned labored and unsure. The man searched about, lost for something to say.

I am talking of Frank Sinatra, but I could be talking of any artist caught flat-footed by age and changing times. As the years pass, can they still conjure up magic, and if they do, can they still find an audience who wants to hear it?

Frank has been a big part of my life since I was young. My dad was a fan, and we often listened to the Sunday with Sinatra show of long-time Philadelphia DJ Sid Mark. I have warm memories of driving around on a glorious Sunday afternoon, my parents in the front seat, my sisters and me in the back, and Sid Mark’s show easing through the speakers. Frank, Sid, and a breezy Sunday. It all seemed to go together.

When I was in high school, Sinatra came to town on his Diamond Jubilee Tour. My dad and I thought about going, but this was in the early 1990s, and Frank was in those autumn years, those wilderness years. We weren’t so sure we wanted to see the voice falter. We feared it would be like seeing an aging ballplayer who staggers about the batter’s box, no longer able to hit a curveball.

I never did see Frank in concert. When he died in 1998, I went out that night and toasted him with his drink of choice: two fingers of Jack Daniels, three ice cubes, and a splash of water.


All these years later, I am now a husband and father with a mortgage and a career, but the man is still never too far from my mind.

Not too long ago I found myself with some rare free time in the college town of Brunswick, Maine. In a record store that has somehow managed to survive in the digital age, I stumbled upon something unexpected.

On the floor was a bunch of old cassette tapes strewn about in a cardboard box. “Take a look,” a sign read, “you know you want to.” The cassettes were a quarter apiece. Most of the world has moved on from cassettes, but my old Toyota Corolla is equipped with a tape player, so I rummaged through the box. Hidden amongst musty AC/DC and Eagles tapes was Frank Sinatra’s Trilogy: Past Present Future album.

I promptly put my money down.


Trilogy came out in 1980. I was 5. I didn’t know it at the time, but my father bought it just after being laid off, as a present to himself during a tough time. I always remember the album in his record collection. A three-disc set, Trilogy felt hefty and important to me as a kid. It contained a lot of music. The first disc, titled The Past, was a mix of old standards, and the second, The Present, offered Frank’s take on newer material. The third disc, The Future, was an original suite of songs by Gordon Jenkins, one of Frank’ long-time collaborators.

The big song on Trilogy was the showstopper “Theme from New York, New York,” probably the last great song of the man’s career. But Trilogy, while it suffers from boring and maudlin moments, features other solid tunes. “You and Me (We Wanted It All),” a tale of two proud lovers in love with being in love but unwilling to do the hard work needed to sustain it, is a favorite of mine. As is his take on “Something.” Frank called it the greatest love song ever written, and he seemed intent on bringing something new to the song, on wresting control of it from The Beatles and making it his own. He once could do this at will. He owns the definitive version of so many standards, but then the 1960s caught up to him. The music, the culture, the whole dang world, was changing fast, and the one-take singer, who once was so assured, felt adrift and went so far as to retire from music in 1971. 

The retirement proved short-lived, but by the time Trilogy came out, Frank hadn’t released an album in six years. Finding music he could connect with and sing had become too difficult. Nothing spoke to him anymore. “When all the songs are out of tune and all the rhymes ring so untrue,” he sang on 1973’s “You Will Be My Music.” “When I don’t find the words to say, the thoughts I long to bring to you.”

We never listened to the third disc, The Future, as a kid. So with my newly bought Trilogy, a three-cassette package that can sit squarely in the palm of my hand, that tape is the first one I pop into my car’s player. What comes out of the speakers is not “Witchcraft,” “Summer Wind,” or a hundred other classic songs you could name. This is different, daring, and, to be honest, downright weird.


The sound of The Future is big and expansive. According to a Billboard article marking the 35th anniversary of Trilogy, The Future was recorded over two days at L.A.’s Shrine Auditorium, once a frequent venue for the Academy Awards ceremony. The Shrine was chosen in large part because of its size. Featuring an orchestra of 140 and a chorus of 50, the recording session was the largest of Sinatra’s career.

Putting himself through extensive rehearsals, Sinatra took about a year to learn all the material that makes up the album. One song ponders coming technological innovations (“rockets, spaceships, computers, inventions,” the army of background singers belt out like a Greek chorus) while another, “World War None,” makes a plea for world peace. In the strangest track, Sinatra takes the “Satellite Special,” an Amtrak-like rocket ship, and tours the solar system. He looks for romance on Venus, labels Pluto “a rotten place, an evil misbegotten place,” and is certain Uranus is heaven because pizza and a little red wine are waiting for him there. Once or twice, as the Satellite Special makes its way, the music takes a foreboding turn, sounding like something out of a 1950s horror movie about monsters or murderous aliens.

Beyond the sci-fi meanderings, The Future is personal. Sinatra had always been revealing in his songs, but from the first words where he introduces himself, singing “My name is Francis Albert,” he takes us into his life. He looks on his youth in Hoboken, on his glory years in Vegas, and dwells on aging and his own mortality, contemplating what will happen “when the music stops.”

At one point he sings, “Quite a different song must be sung, when the singer is no longer young.” Indeed, this is quite different, an ambitious and crazy mess of a record, and I’m not sure what to make of it.


Neither did anyone else when it first came out.  One New York DJ called The Future “narcissistic” and a “shocking embarrassment.” The New Yorker labeled it the “silliest venture the singer has ever got himself into.” I asked my dad about it, but he was just as perplexed as me. He never could connect with the disc, so he didn’t bother listening to it, akin to putting on The Beatles’ White Album and skipping “Revolution 9.” The podcast “You Must Remember This,” which examines the lost history of Hollywood, devoted an entire episode to The Future, but no one connected with the album wanted to talk about it on the record.

I decided to reach out to the great Sid Mark. This was a few years before he passed away in 2022, after an amazing 65 years of playing Sinatra on the radio. I emailed him for his impressions of The Future, and I was happy to see him email me back. “I’m probably one of the only people who has played it in its entirety any number of times,” Sid wrote. “I find it to be fascinating and interesting. In speaking with Mr. S., we discussed how it would have made a great soundtrack for a movie or TV show. The standout track from that would be ‘I’ve Been There.’”

I get a kick picturing Sid breaking bread with “Mr. S,” but the legendary DJ’s email leaves much unsaid about The Future. Tellingly, his favorite track is the disc’s most conventional.


I remain a Sinatra fan for life. The music still fills me up, makes me feel lighter. When I ride around with my daughter, I play her Sinatra, but I stay away from The Future. I focus on the classics from the golden era, from say the mid-1950s to the mid-1960s, before it all started to slip away from him. At first, I’m not sure if she likes the songs. But then, after a few listens, they sink in. I catch her singing them, and I feel that I’ve done my job as a parent. My daughter may not always eat her vegetables, but she likes Sinatra.

Riding alone is when I listen to The Future and try to decipher it. I grasp for lyrics that might mean something to me. At one point Frank sings, “I reached the age of 40 somewhat sooner than expected, living at a fairly hectic pace.” I’m at that age now, though my 40s are obviously much different than Frank’s. Life for me is a rush of family and career, of things to do, of drop-offs and pick-ups, but in his 40s, Frank was very much in his swinging, ring-a-ding-ding prime. 

But The Future really isn’t about being 40. This is an older man’s record. No longer cool or at the peak of his powers, Frank sings about being at his house in the desert, a drink in his hand, looking up at the stars. He’s reflecting on his life and the future, the things that he won’t live to see, his wishes for his children.

Of course, one can’t discuss The Future without mentioning its weirdness, especially Frank’s Star Trek-like venturing among the planets. No doubt about it, the record is peculiar, even wacky, and we can argue about the strength of the melodies and lyrics and whether the whole enterprise ultimately hangs together. But I admire Frank’s guts for making it. At the age of 64, at a time when he felt disconnected from contemporary music, he took an artistic risk. The culture may have pushed him to the side, but he wasn’t done being bold, at least not yet. He was still trying, still going for it.


When I listen to The Future, driving in my old Corolla through staid and sleepy suburban streets, that boldness, that resolve and creative restlessness, is what I think about most of all. How long can someone keep that fire, I wonder. How long can that flame burn in an artist before it’s extinguished by age and the passage of years?

For a time, The Future kindled a resurgence in the studio for Sinatra. In 1981 he released the overlooked but solid She Shot Me Down, a collection of saloon songs, the hard-luck tales of loss and heartbreak that were a trademark. The slick L.A. Is My Lady, produced by Quincy Jones, followed in 1984, but then came another dry spell. Just like before, the albums stopped coming, the man seemingly having nothing new to say. Nearly a decade passed before Sinatra released the tossed-off Duets album in 1993. A sequel followed in 1994. The albums felt sterile, but both were big sellers.

But all along, he continued touring, which in hindsight doesn’t seem too surprising. He predicted as much on The Future. “When that cat with the scythe comes tugging at my sleeve,” he sang, “I’ll be singing as I leave.” Sinatra didn’t sing until the bitter end, or the “final curtain” as he puts it on “My Way,” but he came close. An inner urgency kept him going, even as his body began to break down. There were some rough nights, his voice shaky, the words forgotten, the man shuffling about the stage in a fog. Again, I admire his resolve. Sure, my dad and I had passed up a chance to see him during this time, but over the years, I’ve come to appreciate that drive to keep stepping on stage, to walk that tightrope again and again. Frank wasn’t content to stare off into the desert and quietly slip away. The music had to be served.

Sinatra gave his final performance on February 25, 1995, some 15 years after The Future originally came out, at the end of his annual golf tournament. In an invitation-only event at the Marriott Hotel in Palm Desert, California, he delivered a short but strong six-song set that closed, fittingly enough, with “The Best Is Yet to Come.”

— John Crawford is a writer and editor in the Boston area. His work has appeared in The Threepenny Review, The Smart Set, Points in Case, and other publications. He can be found on Twitter, @crawfordwriter, where he writes weird, depressing, semi-amusing missives about climate change.

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