No Longer Possible to be the Hippest Guy in the Room

Alex Gibney’s “All or Nothing at All” HBO Documentary Films production makes an interesting statement about three hours into its four hour runtime. By the mid-1960s, it was no longer possible for Sinatra to be the hippest guy in the room.

This statement speaks worlds about how we in the western world define “hip” as being aware of, and impacted by, what is happening in the culture we share with members of the communities in which we live. This is a state of awareness that, on many levels, is exclusive to people between the ages of 10 and 50. It may start earlier and last a little longer than that age range, but eventually people age into a state of reduced cultural awareness. We stop finding the new stuff interesting – in fact, likely see it as just some faddish expression of human fascination that we have seen before – and we stop changing. We stay stuck in our time and age in place, which is why my 97-year old mother-in-law still dresses like Jackie Kennedy, and why I pleasantly consider some future event to which I might again wear my Beatle boots.

Middle-aged Frank Sinatra, particularly in retrospect, seems a little creepy, with his sunshine fedoras and cheap-looking suits. He never really wore clothes well, too scrawny in his youth, and too dowdy in his middle years. He developed a hurt-back kind of walk, a little like old George Burns, and guys like that are usually looking for their hair-pieces, as everybody knows. So, it is hard to portray hip through all of that. The Sinatra of the ‘60s – after he had helped John Kennedy be elected president, been snubbed by the political elite, and given himself, for a time, to international charity – was sort of sad, even while being the huge star that he still was on the strength of his legend. Sinatra was doing television shows, but his recording career was dead. He put out an album titled Watertown, which I had never heard of before watching the Gibney film, but featured songwriter John Denver, that sold only 30,000 copies. Sinatra’s recording career had died before, then been resurrected at Capitol Records with Nelson Riddle. He started his own label with Reprise Records, foreshadowing a time in the future when big labels couldn’t support the flood of acts existing in the music business, when self-run recording operations would finally become the norm.

Sinatra had championed the immigrant class, including African-Americans, as they were called at the time. In 1945 he had done the short film “The House I Live In”, in which he played big brother (not in the Orwellian sense) to a bunch of kids from the neighborhood, explaining the virtues of acceptance of people from all races and classes of society. It was a pretty blatant attempt to get Frank Sinatra, who got a medical deferment that kept him out of service in World War II, on the right side of public opinion. That said, it was Sinatra at his very best. He was a good actor and he knew how to turn on the charm.

In fact, it was Sinatra’s uncanny ability to take a cheesy concept, and turn it into a masterful work of art, that separated him from virtually every other performer in the world. That almost no one else has actually been able to do that over the course of a 50 year career, as did Sinatra, attests to how rare of a bird he was. And it also explains why lounge singers doing Sinatra songs are so unbelievably horrible. Sinatra had done the course in vocal development, so he could sing like a saxophone, and he had a great ability to recognize songs that he could make his own, and somehow those assets conspired to overwhelm his otherwise execrable personal tastes. On face value alone, Sinatra started looking like Rodney Dangerfield at the country club way back around the time he started playing Las Vegas in 1951. He built that tacky town, which remains to this day a place that is a reflection of the baseness that really drove much of Sinatra’s long exercise in hedonism.

Can You Trust this Guy?

One might ask Sammy Davis, Jr., were Sammy still around to ask. Frank Sinatra had been an important ally of prominent Black figures in American society, and one-of-the-boys among the Blacks who played in his orchestra. Sinatra’s band leader was a very young Quincy Jones. Sinatra had gained street cred with the Black community by threatening to walk if the Vegas casinos that he played discriminated against his Black friends regarding housing arrangements. He did fundraisers for the NAACP and he stumped for Jack Kennedy, who Black political leaders, like Martin Luther King, Jr., were placing a great deal of hope in. The coolest performance clip in the Gibney piece shows Sinatra playing a prison in Washington D.C., with the Count Basie orchestra, where a virtually all-Black population demonstrates their approval. Sinatra never seems more real.

Sinatra had borrowed the name of the Rat Pack from a Hollywood contingent built around Humphrey Bogart and his friends, and he created a Vegas version that included the versatile entertainer Sammy Davis, Jr. Davis was an explosive talent, able to dance, play drums like Gene Krupa, and sing with range and emotion, and his inclusion in a stage act that featured Dean Martin, Joey Bishop, and Peter Lawford, seemed like an important signal to send in the United States, where the civil rights movement was gaining steam.

But then something weird happened. Sinatra and his White friends started making Sammy the butt of racist jokes, which Sammy Davis, Jr. went along with for reasons known only to him. His willingness to accept this very public Uncle Tom role infuriated those Blacks who had felt so supported by Sinatra’s championing of their cause. It got even weirder after the 1960 election, when Jack Kennedy won with the help of Sinatra’s Chicago mob connections, and then promptly invited Sinatra’s sidekick Sammy Davis, Jr., out of the picture. They didn’t want him, and his biracial marriage, to be a part of the inauguration festivities. The Kennedys – the hope of the civil rights leaders – were showing a racist side.

In fact, the Kennedys not only snubbed Sammy Davis, Jr., but soon enough they dropped Sinatra, as well. Sinatra had reportedly taken a tongue-lashing from his mob friends, after the newly elected JFK named his mob-busting brother to be Attorney General of the United States. The mob figured Kennedy owed them the favor of backing off on investigations into their activities, and that Sinatra was their go-between guy who would make that happen. Sinatra and Jack Kennedy had been play pals on the West Coast, diving in the same flesh pools of Hollywood, and Sinatra reportedly loved Jack Kennedy, who turned out to be a guy he couldn’t trust.

Sinatra not only dumped Sammy Davis, Jr., he essentially dumped the entire civil rights movement when he switched allegiances to the Republican Party and started supporting people like Ronald Reagan and the corrupt Nixon vice president Spiro Agnew. Sinatra, who had been a life-long Democrat, was widely thought to be supporting Republicans to get back at the Kennedys, who had misused him all those years earlier. That would make his political switch something like a vendetta, and very Italian.

The New Pollution

In 2015, Frank Sinatra feels like a ghost of a long-ago time. The world that he personified – the “Come Fly with Me” enthusiasm about an age that would introduce a fabulous new world of globe-trotting adventure – turned out to be one in which coach class didn’t even offer room for your legs, let alone microwaved meals. Audiences in 2015 are much less inclined to ride as happy passengers on somebody else’s flight of ego. The era of the Sinatra-style “star” has yielded to the world of the Kanye West-style celebrity, which is more car-crash voyeurism than absorption in someone else’s artistic expression.

It could be argued that, in 2015, there is a societal rejection of the perceived phoniness of the Sinatra-style personality, though Sinatra’s Rat Pack mentality does continue to live on among the Hip Hop community and to inhabit the inner worlds of Justin Beiber and Marshall Mathers. But none of what these latter-day star hedonists do really matters, the way Sinatra did in his time. We are in an era of anti-hero worship, which probably underlies the current fad with body tattooing, with average citizens emulating a look that previously belonged only to ex-convicts, motorcycle gang members, merchant marines, and carnival freaks. Everything about today’s style is a rejection of shining phoniness, which shows up now in public opinion research that indicates that young people today put very little emphasis on individual artists. They like songs, but could hardly care less about the people who produce them.

Certainly a part of this change in public perception must be that people have gotten sick of unextraordinary people living large in a world of generally diminishing returns. In fact, people no longer use that cliché – living large –because the concept now seems so out of reach.

Sinatra, who evolved Bing Crosby-level celebrity to its “Jet Age” form, left the world that followed with a template that seemed absurd as we moved toward the “Digital Age”. He lives on today as a kind of a caricature that we still recognize immediately, but that precious few can portray in any effective way. Harry Connick, Jr. does a fair representation of Sinatra’s style, as does Michael Bublé, but that is all on a superficial musical level. Sinatra was music plus his own unique personality and backstory, and the contemporary world offers no support for a phenomenon such as that. Nobody knows, or even wants to know, Michael Bublé’s back story, because inevitably it would be that of some aggressive, fame-seeking kid leaping over walls to achieve his selfish ambition. We’ve seen all that – saw it in Frank Sinatra – and it is nauseating. Sinatra killed the mega-star artist, making the label his forevermore by virtue of the fact that the well dried up for his particular brand of super ego.

Frank Sinatra's 1966 Retirement Concert