Sinatra: Still the Chairman at 100

The iconic crooner didn't just sing his songs — he lived them

In truth, there were probably better vocalists. Vic Damone and Jerry Vale had much better instruments and certainly more range than Sinatra ever had. But they lacked his acting ability. Remember, Sinatra was part of the studio system.  He studied acting with Stella Adler and others, people who taught him to view every lyric as a text, a monologue set to music. Others sing along to the American Songbook, Sinatra sang through it — bringing his whole experience to each tune. 

Others had introduced much of what would become Sinatra’s canon. “I Get a Kick Out of You” was Ethel Merman’s song, “New York, New York” was written for Liza Minnelli, “Night and Day” and “One For My Baby” were Fred Astaire tunes, “The Best Is Yet To Come” was introduced by Tony Bennett. 

Other torch songs and ballads first belonged to Bing Crosby or Billy Holliday, both of whom profoundly shaped Sinatra’s style. What made a Sinatra performance special was his strong point of view, a connection to the material that was his alone. The combination of impeccable phrasing (absorbed while standing in the shadow of trombonist Tommy Dorsey), precise enunciation, and the ability to inhabit a lyric made Sinatra the singer he was — and still is.   

He came into his own in the early 1950s when he left both the love ballads and the Columbia label and signed a deal with Capitol Records. There, he was paired with the great Nelson Riddle. 

Riddle’s orchestrations created the Sinatra sound and allowed the band singer to soar and truly get “under our skin.”

Frank Sinatra’s masterworks are really touchstones of American culture at its zenith. Sinatra was the Walt Disney of music — a man with such artistry that more than half a century later he is still being imitated. But what he had is unrepeatable. 

Sinatra benefited from the genius around him and occupied a stunning period of popular American song. He personally collaborated with our greatest songsmiths. Cy Coleman, Sammy Cahn, Jimmy Van Heusen, Johnny Mercer, Harold Arlen, Cole Porter, Irving Berlin, the Bergmans, and Ira Gershwin all wrote for Sinatra. These men breathed the same cultural air. Their music rose up naturally from their time. 


And though that time is no more, the sweetness of their music remains. Ever wonder why there has never been another Sinatra? The fertile ground of that post war, yearning culture is long gone — our innocence is shot and we are somehow no longer that honest or human. 

“Autumn in New York,” one of my favorite Sinatra songs, has the lyric: “It’s good to live it again.” It seems to me whenever you hear a Sinatra song, that’s what happens. Sinatra allows us to live those songs again, stirring up the highs and lows we all share. 

Frank Sinatra didn’t just sing songs, he let the songs sing through him. His hurt over being left by Ava Gardner, his Rat Pack swagger, the boyish joy of the kid from Hoboken is always right there on the surface wrapped in a perfectly phrased, street-wise eloquence.  

I have a treasured bootleg of Sinatra studio sessions that should be officially released. There you can hear Frank the craftsman, feeling his way through the charts with the orchestra. He is usually obsessed with perfecting the tempo, often snapping out the beat until the drummer or pianist catches up with him. In one session he instructs Nelson Riddle to come in on a downbeat. He stops and restarts the orchestra repeatedly until it is just right. For a man who could not read music, Sinatra had an astounding command of the form. Even late in his career, I can remember him in concert quieting the horn section or barking commands to the conductor off mike in the middle of a song.  

In those later years (as you can see from the videos above), he became a living Smithsonian of the American Songbook. No matter how frayed the voice, he respected his audience, gave it his all and revered the music.

In the middle of nearly every show, he would pour himself a little Jack Daniels or Chivas Regal, raise a glass and offer a toast, “May you live to be 110 and may the last voice you hear be mine.” Given his supreme artistry, there’s a great chance it will be. 

Happy 100th, Frank. And thanks for always doing it your way.

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