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Pat MurphyFrank Sinatra, who would have been 100 this December 12, was unique among his pre-rock ‘n’ roll peers. As the likes of Bing Crosby became old fashioned and out of touch, Sinatra largely escaped such a fate. And by anyone’s definition, his life was multi-faceted.

Sinatra was a singer with over a thousand different recordings to his name; he was a movie actor who won an Oscar for his dramatic performance in From Here to Eternity; he was a cultural icon who came to signify a hedonistic hipness we now associate with the likes of Mad Men’s fictional Don Draper; and he was a political animal whose lifetime trajectory took him from Roosevelt Democrat to staunch Reaganite.

First and foremost, though, Sinatra was a uniquely skilled interpreter of popular songs. And while he was gifted with a distinctive voice, a keen ear and impeccable timing, perhaps his most distinguishing musical feature was the care he took with lyrics. Unlike many others, he didn’t merely sing notes with the words as an afterthought. If anything, the words took precedence.

Writing recently in The Wall Street Journal, biographer James Kaplan tells the story of Sinatra’s own explanation of his technique. Apparently, he would begin with a sheet containing just the lyrics, essentially viewing the song as a poem and trying to come to grips with the underlying emotions. Then it was a matter of speaking it aloud in order to get the right inflections, all of which took place before the words were reunited with the music.

However, if Sinatra’s musical output was generally characterised by quality and taste, the same can’t be said for his film career. It wasn’t that he lacked screen presence or that he couldn’t act. Far from it.

Instead, the problem was a matter of interest. If Sinatra cared for a role, he could be very good in it, particularly when it came to dramatic pieces like The Man with the Golden Arm, The Manchurian Candidate, and The Detective. But if he had contempt for the material or if he got bored, it was a horse of an entirely different colour. And several such horses, alas, appeared in his later years.

Then there was the cultural icon dimension. To say that Sinatra liked wine, women and song would be putting far too romantic a spin on it. As the finger-snapping leader of the famous Rat Pack, he was a hard-partier with a “booze and broads” sensibility, one in which women were often dispensable commodities, sometimes even just rented for the occasion.

Along the way, Sinatra became the swaggering symbol of a particular kind of male ideal. Or perhaps fantasy would be a better term. Power and money, lubricated by unlimited alcohol and sex, constituted the essence of the fantasy’s aspiration. And however we may pretend to tut-tut at that model now, it had substantial popular resonance a half-century or so ago.

Finally, there was the politics. Initially an active liberal Democrat campaigning for the likes of Franklin D. Roosevelt and Harry Truman, Sinatra came into full flower with John F. Kennedy, a man whose interest in politics and power, style and sex, matched Sinatra’s own. They became at least very good acquaintances, so much so that Sinatra even undertook the role of Kennedy’s sometime procurer.

And the political involvement went deeper than the usual celebrity schtick. At critical times in the 1960 campaign, Sinatra reputedly acted as middleman for the Kennedys in situations where Mafia support was invaluable, such as West Virginia during primary season and Chicago in the general election.

Then it all went sideways. In the spring of 1962, Kennedy, now president, switched his vacation plans and stayed at Bing Crosby’s Palm Springs home rather than Sinatra’s. Kennedy’s motivation was political – fear of publicity about Sinatra’s mob connections. But Sinatra, to whom loyalty was a prime virtue, wasn’t to be mollified.

In January 1981, 20 years after he’d organized Kennedy’s pre-inaugural gala, Sinatra did the same for Ronald Reagan. Whether that represented a genuine political migration – one that Reagan himself had undertaken in the 1950s – or whether it was another manifestation of what biographer Kaplan describes as Sinatra’s addiction to power is anyone’s guess.

Still, whatever one may think or say about Frank Sinatra, he certainly had a way with a song.

Pat Murphy casts a history buff’s eye at the goings-on in our world. Never cynical – well perhaps a little bit.

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