Frank Sinatra was depressed. Not the "I’m having a bad day" kind of blue, but a deep, career-threatening funk that had him questioning if he even belonged in the late 1960s. The world had changed. The Beatles were everywhere. Flower power was the new currency, and the tuxedo-clad Chairman of the Board felt like a relic. Then came cycles by frank sinatra. It wasn't just another album; it was a surrender to the passage of time.
He recorded it in 1968. Think about that year for a second. Vietnam was screaming, MLK and RFK were gone, and the youth culture was vibrating with psychedelic fuzz. Into this chaos walks Sinatra, nearly 53, looking at a stack of songs by guys like Joni Mitchell and Glen Campbell. He didn't want to do it. Honestly, he hated some of the material initially. But his producer, Don Costa, knew Frank needed to bridge the gap between the saloon songs of the fifties and the folk-rock sensibilities of the hippie era.
The Sound of a Man Admitting Defeat (and Winning)
The title track, "Cycles," written by Gayle Caldwell, is basically a masterclass in existentialism. It’s got this looping, repetitive melody that mirrors the lyrics perfectly. Up and down. Round and round. Most singers would have over-sang it. They would’ve tried to make it a grand anthem. Sinatra? He did the opposite. He sang it like a guy sitting at the end of a bar at 2:00 AM, realizing he’s made the same mistakes five times over and will probably make them again tomorrow.
"So I've been down and I've been out..."
You hear that grit? That’s not a vocal effect. That’s a man who had lived through the Ava Gardner heartbreak, the career slump of the early fifties, and the crushing weight of being "The Voice" in a world that suddenly preferred Jim Morrison. Cycles by frank sinatra captured a specific kind of middle-aged vulnerability that was incredibly rare for him. Usually, Frank was the cocky guy in "My Way." Here, he's just a guy who’s been "shattered" more than a few times.
People often forget that this album was a huge pivot. Before this, Sinatra was leaning heavily into the swing of Billy May or the lushness of Nelson Riddle. But for Cycles, the arrangements felt leaner. They felt... tired. In a good way. Like a well-worn leather jacket. He covers "Both Sides Now" by Joni Mitchell, which is a wild choice if you think about it. A fifty-something crooner singing a song written by a 21-year-old folkie. It shouldn't work. But because Frank had actually lived both sides of life—the heights of the Rat Pack and the depths of being dropped by his label—it carries a weight Joni couldn't even fathom yet.
Breaking Down the Tracklist
It’s not all folk-rock, though.
Take "Rain in My Heart." It’s a massive, sweeping Teddy Randazzo production that feels more like a movie score than a pop song. It’s dramatic. It’s loud. It contrasts sharply with the quiet desperation of the title track. Then you have "Little Green Apples." Now, look—Bobby Russell’s lyrics can be a bit saccharine. "God didn't make little green apples and it don't rain in Indianapolis in the summertime." It’s cheesy. But Sinatra delivers it with this conversational ease that makes you believe he actually cares about the morning coffee and the kids' school.
He also tackled "Gentle on My Mind." John Hartford wrote it, and Glen Campbell made it a standard. Sinatra’s version is different. It’s less "rolling down the highway" and more "remembering the highway from a penthouse window." You can tell he’s trying to figure out how to fit his phrasing into this new, wordy style of songwriting. Sometimes he trips over the meter slightly, but that’s the charm. It sounds human.
Why 1968 Was the Make-or-Break Year
The music industry was basically a different planet by the time cycles by frank sinatra hit the shelves. Warner Bros. (who owned Reprise) was worried. They had Jimmy Hendrix and The Grateful Dead. They had "cool." Sinatra was "Dad's music."
But something weird happened. The kids actually liked Cycles. Or, at least, the adults who were trying to keep up with the kids liked it. The album peaked at number 18 on the Billboard 200. That’s massive for a guy who many critics had written off as a "has-been" just a few years prior. It went gold. It proved that the "Sinatra sound" wasn't tied to a specific genre like jazz or swing, but to a specific perspective.
He wasn't pretending to be a hippie. He didn't put on a fringe vest or start singing about LSD. He stayed in the suit. But he changed the conversation. He started talking about the "circles" of life, the repetition of failure and success, and that resonated with a country that was currently tearing itself apart.
The Technical Side of the Record
Don Costa was the MVP here. If you listen to the strings on "Moody’s Mood for Love" or the way the guitar sits in the mix on "By the Time I Get to Phoenix," you see a bridge between two worlds. Costa managed to keep the orchestral dignity of a Sinatra record while using the rhythms of late-sixties pop.
It wasn't easy. Frank was notorious for his "one-take" philosophy. If he didn't feel it immediately, he’d walk out. During these sessions, there was tension. He didn't always "get" the newer songs. There’s a story—maybe apocryphal, maybe not—of him getting frustrated with the phrasing of some of the folkier tracks because they didn't have the clear "beginning, middle, end" structure of a Cole Porter or George Gershwin tune. They were "circular." Hence, the title.
The Critics and the Legacy
Not everyone loved it. Jazz purists hated it. They felt he was "slumming it" by singing Glen Campbell and Joni Mitchell. They wanted the swing. They wanted the finger snaps. They called it "Sinatra-Lite."
But looking back with 2026 eyes? Those critics were dead wrong. Cycles by frank sinatra is arguably his most "modern" album. It’s the precursor to the "Watertown" album, which was even more experimental. It showed that Sinatra had the emotional intelligence to adapt. He wasn't a museum piece; he was a living, breathing artist who was feeling the pressure of a changing world just as much as anyone else.
📖 Related: The Gene Hackman Obituary New York Times Readers Needed: What Really Happened
The song "Cycles" became a staple. He performed it on his TV specials. He sang it with a certain weary grin that told the audience, "Yeah, I'm still here, and I've seen it all before." It’s a song about resilience. It’s about the fact that if you wait long enough, the wheel turns, and you're back on top.
Practical Ways to Appreciate the Album Today
If you're just getting into Sinatra, don't start with the hits. Don't go straight for "New York, New York." Do this instead:
- Listen to "Cycles" at sunset. There is something about the orange light and that specific arrangement that just clicks. It’s a transition song for a transition time of day.
- Compare his "Both Sides Now" to Joni Mitchell’s original. Notice how she sings it like she’s discovering a secret, while Frank sings it like he’s reporting back from a war zone. Both are valid, but Frank’s version is much heavier.
- Watch the 1968 TV Special. You can find clips of him performing these songs. Pay attention to his hands. He’s often fidgeting or holding a cigarette (of course), looking slightly uncomfortable with the material, which makes the performance feel raw and honest.
- Read the liner notes. If you can find an original vinyl copy, the notes give a great glimpse into the mindset of Reprise Records at the time. They knew they had something different on their hands.
Sinatra’s career is often divided into "The Columbia Years," "The Capitol Years," and "The Reprise Years." Usually, people point to the Capitol years as the peak. But the Reprise era, specifically the late sixties, is where the man became a myth. He stopped being just a singer and became a symbol of survival.
Cycles by frank sinatra is the sound of survival. It’s the sound of a man realizing that he doesn't have to be the youngest or the loudest to be the most important person in the room. He just has to be the one who tells the truth. And the truth, in 1968, was that life is a series of loops. Sometimes you're the windshield, sometimes you're the bug.
Next time you feel like you're stuck in a rut or that the world has moved on without you, put this record on. It won't give you a pep talk. It won't tell you everything is going to be perfect. But it will remind you that the "down" part of the cycle is just as natural as the "up" part. That’s the Sinatra way.
Next Steps for the Sinatra Enthusiast
To truly grasp the impact of this era, hunt down a high-quality vinyl pressing of the 1968 Cycles album (Reprise FS 1027). Digital remasters often compress the dynamics, losing the subtle grit in Sinatra's lower register during the title track. Once you've internalized the weary folk-pop of Cycles, move immediately to his 1970 follow-up, Watertown. It’s a narrative concept album that doubles down on the melancholy and serves as the perfect "Part Two" to the psychological state Sinatra inhabited during the Cycles sessions. These two albums represent the "Vulnerable Frank" era—a necessary counterbalance to the swaggering "Ring-a-Ding-Ding" persona the public usually remembers.