Chairman of the board: how Frank Sinatra sparked the trend for pop star turned CEO

From The Beatles to Jay Z, generations of artists followed Sinatra’s lead in setting up their own record labels

CIRCA 1950: Pop singer Frank Sinatra poses for a portrait sporting a hat and bow tie and showing off a ring on his pinky in circa 1950. (Photo by Michael Ochs Archives/Getty Images)
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Even superstars need an escape plan.

This was a growing concern Frank Sinatra had in the late 1950s, when he was in the midst of his second wave of musical success.

With his career riding high on the back of stellar comeback albums In the Wee Small Hours (1955) and 1958's Only the Lonely, Ol' Blue Eyes felt increasingly chafed by his contract with Capital Records and was looking for a way out.

In trademark mercurial style, instead of signing another big cheque with a rival label, Sinatra opted to instead create one himself.

Just over 60 years ago, on February 13, 1960, he launched Reprise Records – widely viewed as the first label owned by a pop act.

It was a pioneering achievement, resulting in one of Sinatra’s most enduring monikers: the Chairman of the Board.

Hitting the ground running, the company signed his fellow Rat Pack members Sammy Davis Jr and Dean Martin.

Others to join included singer Bing Crosby and jazz maestro Duke Ellington. Even racy comedian Redd Foxx got a look in and signed a deal.

The reason for such uptake wasn't just his star powers; it was Sinatra’s pitch to fellow creatives. Contracts included the dream end goal of the music business: full creative control and the future option of full ownership of publishing rights.

With the financial strain of running such an operation, coupled with the demands of Sinatra's own full-time career, Reprise eventually sold two-thirds of the company to Warner Bros three years later.

But, the genie was out of the lamp.

Much to the chagrin of the industry, Sinatra paved a way forward for musicians seeking creative and financial control. Thus began a new era of the artist-turned-chief executive, a multi-hyphenate still as advantageous six decades on.

The Beatles launch Apple Records

Now, if Sinatra’s move was a shot across the bows of major labels, the decision by The Beatles to go solo, contract-wise, showed there was no turning back from this trajectory.

In 1968, The Beatles launched their own company, Apple Records, complete with its own music and film division. While the band were still contracted to major label EMI, Apple Records gave The Beatles a wide berth to introduce artists to the spotlight.

Those fortunate enough to be signed exemplified the somewhat freewheeling nature of the company, which was partly a genuine attempt to launch new talent, as well as being a form of patronage for respected yet unsuccessful artists.

From more than 50 singles and nearly 30 albums released in its first five years, Apple Records launched future star James Taylor and provided a home for Welsh singer and McCartney protege Mary Hopkin, as well as worked with the group's favourite musicians, Ronnie Spector and Billy Preston.

The Beatles eventually lost enthusiasm for the day-to-day running of the operation. The label exists today mostly through the reissuing of past releases.

Madonna shows her maverick streak

A similar experience took place nearly 25 years after Apple Records launched.

Just like The Beatles, Madonna was at the peak of her fame in 1992 with her greatest-hits release, The Immaculate Collection, topping the charts and on its way to selling more than 30 million albums.

Such figures mean significant clout. As part of her $60 million deal with Time Warner in 1992, the singer launched her co-owned entertainment company Maverick.

Partnering with serious industry figures, the company opened multiple offices across the US, scouring for new artists and securing the services of respected underground acts.

This resulted in some big wins and major industry respect.

Maverick released Alanis Morissette's mega successful Jagged Little Pill in 1995 and UK dance group The Prodigy's ground-breaking 1997 album The Fat of the Land. Other eclectic acts buying into Madonna's vision included rockers Lenny Kravitz and Muse, in addition to nu-metal pioneers Deftones.

Describing how such a broad array of artists found a roof under one label, The Prodigy's Liam Howlett explained Maverick's ethos to Q Magazine in 1998. "They respect their bands," he said. "Even the ones who aren't selling."

Jay Z going it alone

What happens if you haven't sold anything at all?

It was a predicament experienced by young and fledgling rapper Jay Z in 1995, when struggling to land a deal with a major label.

Out of necessity, he and associates Damon Dash and Kareem Biggs launched Roc-A-Fella Records as an outlet to release debut album Reasonable Doubt the following year.

With Jay Z’s profile rising due to a steady stream of hits, further New York underground hip-hop acts signed to the label, including Noreaga, Memphis Bleek and DJ Clue.

The growing hype surrounding the boutique venture moved Roc-A-Fella Records to be eventually acquired by major players Def Jam Recordings, with Jay Z acting as chief executive. Under his two-year reign, from 2005 to 2007, the newly solidified label launched the careers of current pop stars Kanye West, Rihanna and Ne-Yo.

Jay Z's success formed a blueprint largely followed by hip-hop stars.

Eminem (Shady Records), 50 Cent (G Unit Records) and Lil Wayne (Young Money Entertainment) all launched their respective careers, either fully or partly, under the banner of their own companies.

While Jay Z, now a fully fledged entertainment mogul, can take pride in seeing his business acumen reflected in today’s music landscape, Sinatra is the one to thank.

In 2009's Empire State of Mind, he paid tribute when declaring: "I'm the new Sinatra, and since I made it here, I can make it anywhere."

Indeed, Sinatra’s upending of the music industry’s laws of gravity 60 years ago was more than an act of bravura. It tells future generations of musicians they can also do it their way.