Doing It His Way

Doing It His Way

Another exclusive behind-the-music story from the staff and management of Angels Grace Hospice (and part two of our two-part tribute to the genius of Frank Sinatra. Part one can be found here).


As we mentioned, Frank Sinatra’s career, for all intents and purposes, can be broken into three chapters. In the first, he was a skinny kid from Hoboken who, during the big band era and World War II, used his velvet voice to make millions of schoolgirls swoon the world over.

In the second, during the post-war 50s, he was the gently aging and sadder-but-wiser crooner who, in a period of personal and professional darkness, and despite some long odds, found a new label, a new sound, and a higher gear. What’s more, in doing so, he also managed to become something of a male icon and give voice to the hopes, dreams, and heartaches of millions of middle-aged American men, just like him.

But it’s the third chapter of Frank Sinatra’s career we’d like to tell you about. Because that was when Sinatra took his career into his own hands and began carving his own path musically.

The breakthrough moment, of course, was when he decided to leave Capitol Records, whom he felt had started to stifle him artistically. Instead, in 1960, Sinatra started his own company, founded his own label, Reprise, and recruited to it, among others, his old Rat Pack cronies, Dean Martin and Sammy Davis, Jr., along with the likes of Keeley Smith, Rosemary Clooney, Duke Ellington and Count Basie.

Indeed, 1960 was when Frank Sinatra woke up one day to find himself with more artistic freedom and creative headroom than he’d ever known in his life. What’s more, with the launch of his own company, it was also when he suddenly found himself with a brand-new nickname – one he reportedly very much liked: the Chairman of the Board.

It wasn’t long, however – it was, after all, the 1960’s, an era of social tremendous upheaval and an almost seismic cultural divide in America – before Sinatra and Reprise were being viewed by millions of Baby Boomers as tired, old, and irrelevant – the very thing, in other words, that those Boomers’ beloved British Invasion music, folk, and rock and roll were supposedly rebelling against.

But the simple fact was, on Reprise, Sinatra began to push himself artistically in bold and often daring directions.

Frank Sinatra Watertown

His LP, Watertown, for example – is a concept album about a working man in a tiny upstate New York town trying to cope with the fact that his wife and the mother of his two young sons had just left them for the allure of the big city – was an almost insane leap of faith, commercially. Even though critics now rave about Watertown, when released it was a financial disaster of almost biblical proportions. But Sinatra didn’t care. It was a story he wanted to tell, and a record he wanted to make.

Around that time, he also brought to Reprise a young singer, songwriter, and producer from Oklahoma to help refine his daughter Nancy’s sound in hopes she could earn herself a few hit records. Lee Hazelwood, a true renegade, and a maverick of the highest order, breathed new life into many of the artists at Reprise, even the older ones. He wrote and produced hits like These Boots are Made for Walking and Sugar Town for Nancy. He wrote, produced and, with her, sang such pop chart-toppers as Jackson, Some Velvet Morning, and Summer Wine.

What’s more, he wrote two hits for a pair of aging Brat Packers that, when released, managed to open the minds and ears of millions of young listeners of Top 40 radio: Dean Martin’s wonderful and slightly countrified lament to life as a homeless, wayward drifter, Houston, and one of the true hidden gems of The Sinatra canon: This Town – a song with a bold, brassy and slightly rough-hewn quality to it, and one that showcased ‘Ol Blue Eyes as never before.

Which, in a roundabout way, leads us to Paul Anka, the former teen idol who, at that point, was trying to transform himself into a full-time Vegas showman. At the time, Sinatra was seriously thinking about retiring. He’d accomplished pretty much all he ever hoped in music – and, now, wanted to go out in style, if not a manner befitting how he’d forged his career.

In his years at Reprise, he’d sung more than his share of reflective and melancholy songs. But he wanted more than just simply looking back. He wanted to go out with an all-new tune that was as much about a man’s sense of pride over his many choices, if not the courage he showed in making them, as it was any sense of retrospection or loss he may have felt looking back.

So, one day he asked Anka to fly out to meet with him. Over dinner, Sinatra kidded the young Canadian singer/songwriter about the song he’d never written for him, the one Sinatra had jokingly asked him to write years prior. But that night, Sinatra shocked Anka by admitting that he was fed up and was quitting. All he wanted, he said, was to do was one more album and then he was done with show business for good.

The Chairman of the Board told Anka to write a song to capture the essence of how he’d lived his life and, especially, the many, often risky career choices he’d made along the way. And he wanted the song written specifically for him.

Going to work immediately, Anka spent that entire night trying to capture the essence of the Sinatra mystique lyrically, while at the same time setting those lyrics to an obscure French melody that he’d happened to stumble upon on a recent trip overseas

Paul Anka
Paul Anka

Finally, after so many fits and starts, and so many hours experimenting at the piano, it hit him. At about three in the morning, Paul Anka, in a flash of inspiration, hurriedly scribbled on a piece paper: “And now the end is near, and so I face the final curtain.”

That single line seemed to open the floodgates for the songwriter. By five in the morning, and with the sun peeking its nose over the horizon, Paul Anka had completed both the words and music to My Way. And a few hours after that he was in the studio laying down a demo of the song – a tape he immediately tucked under his arm to take to Sinatra personally, knowing he was going to be handing the leader of the Rat Pack a song that, in Anka’s words, he “wasn’t afraid to give him.”

So, with that, Angels Grace invites you to spend a few moments with us, reading some of our testimonials, and learning a bit about who we are and what we do.

And while doing so, please take a moment to sample just a few of the songs from one of the most fabled closing chapters in musical history; a chapter during which the legendary Chairman of the Board, instead of taking the easy road, cut the safety net beneath him, struck out on his own, and challenged himself as an artist as he’d never done before.

An era during which, in other words – and as the record shows – Frank Sinatra took the blows and did it his way.

Music can play such a powerful role in hospice care.

“I play music all the time for our patients. I can pull whatever music the patient is interested in at the time.”

~ Angels Grace Hospice Social Worker

“Usually patients  LOVE when I play music! I love it when they sing along.”

~ Angels Grace Hospice Chaplain

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You’ll need a Spotify account to listen to this full playlist otherwise you can skip through the previews below.