Why Frank Sinatra Is Still the Chairman After 100 Years

(photo courtesy of Associated Press)

This coming Saturday, the 12th, would have been the 100th birthday of one Francis Albert Sinatra. Why should you care? And why should we be talking about Frank Sinatra 17 years after his death at age 82?

You should care because Frank Sinatra invented the pop-culture in which you live. He was the original pop star, crossover artist, media mogul, hyphenate, and badass. Diddy, Jay Z, and Taylor Swift all owe their success to the Sinatra playbook. Every artist needs to fight for his or her career. And Sinatra fought harder than most. He was born scarred and partially deaf (due to use of forceps during birth). He spent his childhood in the Great Depression.

For 82 years, Sinatra beats the odds, expanded his influence, and advanced his craft. Impressed with Justin Bieber’s career resurrection? Sinatra was there first. Think Beyoncé and Jennifer Hudson’s film turns are dramatic? Sinatra was there first. Believe that Dre, Jigga, and Kanye are the groundbreaking examples of recording artists who also flex their muscle as record label owners? Sinatra was there first. He’s the original gangster. He wrote the book – whether you read it or not.

Proof of Sinatra’s staying power was on display earlier this week when CBS aired Sinatra 100: An All-Star GRAMMY Concert, featuring Lady Gaga, Zac Brown, Alicia Keys, John Legend, Nick Jonas, and a bunch of other singers not even born when Sinatra was at his prime. Still, they are all smart enough to know they stand in his shadow.

Happy birthday, Saint Francis. You made the world safe for strong-willed, entrepreneurial artists. In an age of musicians being marginalized by subscription services and shorter attention spans, we all can learn from your grit and ability to reinvent yourself.

The Pop Star

One of Sinatra’s first gigs was as a singing waiter in a New Jersey roadhouse. It paid $15 a week. A year later, he was fronting Tommy Dorsey’s big band. By 1942, Sinatra said goodbye to Dorsey (and sued him over royalties) and set out to become a pop star like his idol, Bing Crosby. Columbia Records signed him in 1943 and cranked out four singles, including “Close to You.”

In less than five years, Sinatra was the biggest pop star in the country. Bigger than Bing.

The Comeback

Ol’ Blue Eyes’ potential slide into irrelevance happened as quickly as his initial rise. By the early 1950s, Sinatra was unable to full concert halls, and Columbia dropped him. Enter Nelson Riddle – a fellow New Jersey native and a genius arranger who was the (not-so) secret weapon behind Capitol Records’ biggest recordings. Riddle worked with legends such as Nat King Cole and Ella Fitzgerald, but his Sinatra collaboration would be career-defining for both of them (despite the fact that Sinatra initially refused work with Riddle).

The Sinatra-Riddle recordings represent some of the best American popular recordings ever made. They also give us “The Voice.” At Capitol, Sinatra went from being a great singer to a singular singer. More than 50 years later, these recordings would serve as inspiration to another singular voice: Bob Dylan’s 2015 album, Shadows in the Night, was recorded in the same studio and covered some of the same material.

The Mogul

In 1960, after over 20 years of recording, Sinatra wanted control. He founded Reprise Records and installed himself as CEO (hence “The Chairman of the Board” nickname). The Chairman gave his buddies, Dean Martin and Sammy Davis, Jr., recording contracts. He also gave them – and all Reprise artists – something rarely found in the music business: full creative control and ownership of their work.

Sinatra also recorded some of his most memorable recordings at Reprise, including perhaps his most iconic tune, “My Way.”

Sinatra sold Reprise for a reported $80 million. It was small change for a man who also had multiple real estate holdings, a private airline, and a missile parts company. The former singing waiter’s net worth was reported as much as $600 million at the time of his 1998 death.

The Hyphenate

Sinatra’s film debut was in an uncredited role in a little-known 1941 comedy called Las Vegas Nights. Four years later, Sinatra would truly begin a second career as a film star, when he starred alongside Gene Kelly in the MGM musical Anchors Aweigh. The film won an Oscar for Best Score and received four more nominations, including a Sinatra-sung cover of Jule Styne and Sammy Cahn’s “I Fall In Love Too Easily.“

Over the course of his life, Sinatra starred in 57 films, 24 television projects, and none radio series. He produced, directed, and won an Oscar for Best Supporting Actor for his role in From Here to Eternity, and showed up in The Cannonball Run II. Boom.

The Badass

Frank Sinatra was not a badass because of his style. He was not a badass because he could handle his booze and presumably hung with mobsters (the FBI had a 1,000-plus page file on him). He was not a badass because he ran with the Rat Pack (a name he refused to use, preferring “The Summit” or “The Clan”). And he was not a badass because he could get inside of a song like his life depended upon it.

Sinatra was and is a badass because he endures. His influence was there until the end and still lingers. Witness nearly every hip-hop star’s obsession with recreating his own Rat Pack. Witness every rock star that dares to sing a Sinatra tune in an effort to be seen as a “real” artist.

While other artists talk of their “brand” and grope at merchandising and marketing opportunities, Sinatra simply did it. He was the pop star, the mogul, the hyphenate, and the badass – all effortlessly. Sinatra’s cool transcends genre, race, and age. All roads go through him. All roads lead to him. Long live the Chairman.

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