A Century With Sinatra

He was born 100 years ago. He sang and caroused in hundreds of clubs, so we think it’s apropos that The Chairman of the Board visit one more…The Century Club.

Do you know what we like about Frank Sinatra? He was a badass from jump street and not only had lofty aspirations of being someone you’d remember, but he made sure he was on the right path to do so. And if he wasn’t, then he’d course correct to make sure he continued to get closer to achieving his dreams.

Case in point:

Frank was a fighter. We know this. Maybe it came from his Italian roots or from his parents, his father of which was a bantamweight boxer who fought under the name Marty O’Brien. Regardless, Sinatra held firm to his convictions and it’s an overwhelming reason he ended up building the career that he did. Whether it be with journalists, photographers, studio bosses or ex-wives, there was no tail wagging the dog with this guy and, as a result, his positioning afforded him advancement to where we was looking to go.

Cary Grant, Sinatra’s good friend, once said that Frank was the “most honest person he’d ever met”, who spoke “a simple truth, without artifice which scared people.”


We love his passion and work ethic. On his road to stardom, Sinatra’s obsession kept him very busy and committed, which is right in the wheelhouse for someone who was a workaholic and reportedly only slept for four hours a night on average. He performed in local Hoboken social clubs, sang for free on radio stations and found jobs singing for his supper or for cigarettes. To improve his speech, he even took elocution lessons. He was a perfectionist and did whatever it took.

Then there was his style and apparel. During the Great Depression, his mother Dolly would give him money to buy expensive clothes, resulting in neighbors describing him as the “best-dressed kid in the neighborhood”. This penchant for nice clothes would carry through Sinatra’s entire life. He would later admit that he believed that as he was the best, he had to give his best to the audience, and would wear expensive custom-tailored tuxedos on stage as a sign of respect and to look important.


Sinatra was a survivor. His early rise found him competing with Bing Crosby and, by 1946, Ol’ Blue Eyes was performing on stage up to 45 times a week and singing up to 100 songs daily and making good money.

Then the bottom started to fall out.

A combination of waning popularity, the death of his publicist, reports of infidelity with Ava Gardner and the destruction of his marriage to Nancy coupled with financial difficulty following his divorce and career decline all found Sinatra at new low. At a concert in Chicago, only 150 people in a 1,200-seat capacity venue turned up to see him. By 1952. he was performing at the Kauai County Fair in Hawaii. Sinatra’s relationship with Columbia Records was also disintegrating, with A&R executive Mitch Miller claiming he “couldn’t give away” the singer’s records. Columbia and MCA dropped him later that year. Journalist Burt Boyar observed, “Sinatra had had it. It was sad. From the top to the bottom in one horrible lesson.”

A weaker person would have succumbed to it all.

Chalk it up to Frank the fighter.


1953 is the year that began to bring it all back. The release of the film From Here to Eternity would end up garnering an Oscar for Sinatra. It was noted that Frank began to bury himself in his work, with an “unparalleled frenetic schedule of recordings, movies and concerts”, in what authors Anthony Summers and Robbyn Swan describe as “a new and brilliant phase”. In 1953, Sinatra also signed a seven-year recording contract with Capitol Records.

Sinatra’s pairing with Nelson Riddle, an established arranger and conductor at Capitol who was Nat King Cole’s musical director, was also a game changer. After recording “I’ve Got the World on a String”, Sinatra offered Riddle a rare expression of praise, “Beautiful!”, and after listening to the playbacks, he could not hide his enthusiasm, exclaiming, “I’m back, baby, I’m back!”

Sinatra came to consider Riddle “the greatest arranger in the world”, and Riddle, who considered Sinatra “a perfectionist”, offered equal praise of the singer, observing, “It’s not only that his intuitions as to tempi, phrasing, and even configuration are amazingly right, but his taste is so impeccable … there is still no one who can approach him.”


Welcome back, Mr. Sinatra. You fell down, but you got back up. We like that.

New York, New York. In 1980, he scored a Top 40 hit with (Theme From) New York, New York. This tells us he never stopped competing, performing and giving it his best. Francis Albert Sinatra from Hoboken, New Jersey, never rested on his accomplishments and, because of that, always gave us something to marvel at. From the Rat Pack and Las Vegas to his television and movie appearances and everything in between, that’s Frank Sinatra.

He did it his way – and it all started 100 years ago.