Although certain Hollywood elites are famous for their liberal politics, the entertainment industry itself remains one of the few large-scale examples of a relatively free market. Private property rights, voluntary exchange and the explicit enforcement of contracts are generally the rule. There are no price controls and little regulation in the production of motion pictures, television programs (at least for cable) or the making of records. Entertainment entrepreneurs are perfectly free to combine resources in ways that they believe consumers prefer in an attempt  to make profits for investors or owners. Finally, the industry is notoriously competitive and is an excellent example of Joseph Schumpeter’s theory of creative destruction. 

One does not usually associate Frank Sinatra (1915-1998) with the free market or with entrepreneurship, yet he is an excellent example of both. In the absence of a free market, it is difficult to understand how an uneducated first-generation Italian-American from Hoboken, New Jersey, could have accomplished what Sinatra did in his long career. There is no question that the bulk of that success was due to a prodigious talent. Yet, in addition,  Sinatra was an extraordinary artistic entrepreneur in many facets of his professional life, especially in the business of making records.

Frank Sinatra’s distinguished singing career began in the late 1930s (as a band vocalist for Harry James and Tommy Dorsey ) and ended with the best-selling “Duets” albums in 1993 and 1994.  During the 1940s, he recorded mostly ballads with Columbia Records but it was during the 1950s, when he moved to Capital Records, that the full Sinatra vocal portfolio was on prominent  display. During that period, he recorded dozens of high quality, best-selling albums (he is often credited with innovating the so-called concept or theme album ) and many hundred of iconic singles such as “Young at Heart“ and “All the Way.” Admired by the public and competitors alike, Sinatra was the gold standard male vocalist in the 1950s and 1960s.

Sinatra was not just a popular singer, however. He was also an accomplished movie actor who appeared in musicals such as “On the Town,” “High Society“ and  “Pal Joey” and also won critical acclaim for his serious acting in serious  dramas such as  “The Man with the Golden Arm“,  “From Here to Eternity” (for which he won an Academy Award) and “The Manchurian Candidate” where he delivered the finest performance of his career.  Last but not least, Frank Sinatra had his own television show, was the ultimate concert and  nightclub performer, especially in Las Vegas in the 1960s, and he even once owned his own record company, Reprise Records. Sinatra was the complete entertainment conglomerate.

All of these various activities required a massive creative talent, a driving determination to succeed and an entrepreneurial ability to organize resources profitably; Sinatra owned these qualities in spades. This is most evident, perhaps,  in the hundreds of recording sessions for Capital Records especially, where Sinatra–the total music perfectionist–felt most comfortable and where he operated in an environment he could totally control.

Making records is a complex collaborative enterprise and Sinatra worked with the some of the very best musicians and arrangers of the day such as Nelson Riddle and Billy May. Indeed, the hundreds of Riddle/Sinatra collaborations on Capital Records in the 1950s are considered by many music critics as the high-water mark for the so-called American songbook.

Yet it is only with the recent release of a dozen or so studio out-takes from those years, that we can finally (and fully) appreciate Sinatra’s singular creative genius and his entrepreneurship. We know, of course, that Sinatra did the singing but what many have not realized is that he also selected the songs, commissioned the arrangements and ran the recording sessions like a true Chairman of the Board. The finished product was all Sinatra driven.

The out-take sessions are fascinating in this regard. Listeners often hear a “take one” from the control booth and then an easy run-through of the orchestration with Sinatra participating at a modest vocal level. (In writing, this would be akin to working up the first draft.) Sometimes Sinatra will suddenly stop an early take (“hold it!”) when he fails to cover a note properly or when  he hears a “clam” from some off-key instrument in the band. It is clear from the out-takes that while Nelson Riddle may have been conducting the orchestra, Frank Sinatra was directing the entire recording process. 

As the recording session  proceeds, things get serious as singer and arranger  work through the process of solving problems and making changes in tempo and vocalization. (In writing, this would be the rewriting and revisions phase). At the end of various takes, Sinatra is often heard saying that he wants certain changes or that he wants to hear a playback; but later in the out-takes, when we hear “take 6“, we know that he simply wasn’t satisfied with the earlier versions and that the creative process continued. Some of the classic Sinatra recordings of the 1950s required a dozen or more takes before Sinatra was satisfied and a final finished product emerged.

Creative artists often frown on free market ideas yet the very integrity of their creative process depends heavily on such notions.  Sinatra’s personal politics was often incoherent but his work product and entrepreneurship in recording, now confirmed by the out-take releases, was a genius and pure free market.  

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