Since watching a DVD (a gift from my daughter) with three of Sinatra’s late-60s TV specials on it, I’ve been pondering the crisis that clearly took hold of him when he hit the age of 50.

I can look at this period now with the personal experience of having hit 55 last year, which was the age at which Sinatra announced his (first) “retirement” in 1971. Much as I’d like to retire myself, this was in hindsight an astonishingly young age for an entertainer to announce the end.

It was the TV special featuring easy listening vocal group The 5th Dimension, and Sinatra (jokingly) adopting their Liberace-style costume that got me thinking. This was his clear attempt (in 1968) to get down with the kids and perform music that was somehow more contemporary and relevant than his usual fare. He had absolutely no need to do this, of course, but he was acting out a very public mid-life crisis (his short marriage to Mia Farrow, 30 years younger than him, had just ended) that was culminating, before our very eyes in him perching awkwardly on a stool in a Nehru jacket and beads.

The following year, 1969, his final TV special was just him and a swing orchestra, doing the old stuff, and reminiscing (hilariously) about his Hollywood career, which he was also giving up on.

For me, the crisis that led to his premature retirement started towards the end of his Capitol contract and the beginning of the Reprise years, which I’ve written about before. In 1961/2, his Capitol contract overlapped with Reprise, so that he was recording albums simultaneously for two labels, phoning in performances to fulfil his obligations to one whilst also trying to embark on something new with the other. The cognitive dissonance must have been extreme.

And what was Reprise for, really? A little bigger piece of the pie? Sure, and why not? Which is why so much of the Reprise material consists of re-recordings of his classics from Columbia and Capitol in order to tap the lucrative Greatest Hits market. But give or take the three albums he recorded with Count Basie (including the live one), not much of what he recorded for Reprise was particularly good. And some of it was desperate.

He knew that popular music was changing and he wanted to matter, but at the same time, he hated rock music. He was casting around for new songwriters, but he didn’t know this new material in the way he knew that Great American Songbook. I always thought it was a dead giveaway when he performed George Harrison’s “Something” on one occasion, but credited it to Lennon and McCartney. Anyway, this stuff is painful to listen to. He drags on the beat, his timing is off, he doesn’t swing.

There are four albums that lead up to the retirement.

Cycles comes first, in Christmas 1968. He’s just turned 53. He’s pictured on the album cover sitting on a suitcase and holding the bridge of his nose, as if to say, either, “What have I done?” or “This stuff stinks” – or both! This is an album that features “contemporary” songs from the likes of Joni Mitchell (!), Jimmy Webb, and John Hartford. It was as close as he came to recording a 60s country pop record. It wasn’t a disaster: #2 in the Easy Listening chart, #18 in the Billboard 200 chart.

Then, just three months later, comes his late career motherlode, My Way, which is another pop album, with its title track a version of a French-style chanson, “Comme d’Habitude”, rewritten/reimagined by Paul Anka. Sinatra reportedly didn’t like “My Way” which thus became a millstone around his neck. I personally have always hated the fact that this is the one “everyone” knows. Other tracks on the record include more Jimmy Webb, a song by Ray Charles, a Stevie Wonder number, “Mrs Robinson” and “Yesterday”. Another decent chart performance, #11 in the US and #2 in the UK, but I strongly suspect that Sinatra absolutely loathed this material.

Just five months later, still in 1969, he released A Man Alone, which consisted of songs (or poems?) by Rod McKuen (sort of set to music). Sinatra is still only 53, but this now seems like a man who has given up on life. To quote the Wikipedia: “Despite his popular appeal, McKuen’s work was never taken seriously by critics or academics.” This album hit #30 in the US and #18 in the UK. My mum had a copy. It was terrible.

Finally, Sinatra takes a good long break, sits down and has a Big Think, and a whole seven months later, he releases an experimental concept album called Watertown. The songs were written by Bob Gaudio and Jake Holmes and told the story of a broken man from the titular town. It reached #101 in the Billboard charts, but inexplicably hit #14 in the UK. I don’t remember my mum having it.

(Christ knows what was happening in the UK in 1970. Ted Heath. Jeremy Thorpe. For further context, I’ve previously noted that Layla and Other Assorted Love Songs, also released in 1970, didn’t chart in the UK at all.)

Anyway, Watertown is a flop, Sinatra is done, and the next thing you know, he’s announcing his retirement. Which seems now to be a bit of a flounce, but the voice was still strong in a way that it wouldn’t be later. I think he felt he’d run out of material to record, and couldn’t very well re-record all the good stuff for a 3rd or 4th time. But we know now, in a way people didn’t back then, that he could have given up recording and stuck to the live work. The audience would have continued to be there.

Sinatra’s mid-life crisis lasted at least 5 years, but that core period, 1968-1970, was the hardest for him, I think. My own mid-life crisis seems trivial in comparison. But you want to scream at him, Slow down, Frank! No need for three or even two albums a year. Just wait, the pendulum will swing back your way.

Fellow New Jersey musician Bruce Springsteen last released a studio album four years ago.