I’ve never been a fan of Frank Sinatra or any popular singer/ musician of the 20th century prior to the advent of Rock. I much prefer 19th century music, such as Civil War songs, to much of 20th century popular music. I can appreciate the talent of men like Gershwin, Armstrong, Berlin, Rodgers & Hammerstein, Kahn, Porter, and etc. I can see how certain artists/entertainers were seminal in some way and highly influential, even on Rock, but have a hard time tuning into their sensibility. (Likewise, despite the wonders of Old Hollywood, movies for me really begins in the 1950s, especially with World Cinema.) This extends even to Rock n Roll. Notice how young people today are interested in Rock Music going back to the 60s, but young people in the 1970s hardly listened to anything prior to the 50s/60s. It suggests a continual musical culture for around seventy years, from early 60s to now, with the decisive break having taken place somewhere in the 50s. I don’t recall any of my friends showing any interest in Elvis or 50s Rock n Roll. As for Sinatra and the like, that was considered grandpa’s music.
Plenty of music critics and scholars have heaped praise on Frank Sinatra. Some even claim he was the greatest American singer of the 20th century. Personally, if I had to play old style music, I’d rather listen to Andy Williams, Tony Bennett, and Bobby Darin, to be sure, a rather slippery figure to categorize. If I have a soft spot for a crooner, it’s Engelbert Humperdinck. And some black singers managed to combine more classic styles with the trendier tempos: Lou Rawls especially with “You’ll Never Find”.
Still, one can understand Sinatra’s towering place in 20th century music. More than most performers of his kind, he was able to grow and change while, at the same time, remaining true to his essence. He aged like wine, culminating in “Strangers in the Night” in 1966, perhaps his greatest song. Also, while other singers had prettier voices, his had a richness, a gently intoxicating quality like a glass of rum.
To the best of my knowledge, there was no overt boomer hostility against Sinatra. He just wasn’t on their radar. Besides, even before the arrival of Beatlemania followed by Counterculture, Sinatra had been knocked down a few pegs by Elvis Presley and other Rock n Rollers. There was a sort of the Return of the Italians in the early 60s, but it was composed mostly of Teen Idols like Frankie Avalon. Sinatra had by then become an institution but wasn’t really culturally relevant, just like John Wayne continued to make movies into the 1970s but as a nostalgia act; Clint Eastwood was the one changing movie culture.
Though initially critical of Rock n Roll and Elvis the Pelvis, Sinatra understood the times had changed, and there was the famous duet of him and Presley on TV in 1960. Girls screamed for Sinatra but went crazy for the King of Rock n Roll. (The scene in DINER about Sinatra vs Johnny Mathis shows how Elvis could still be scandalous to those who came of age on the eve of the Rock Era. When Mickey Rourke’s character says he prefers Elvis to both Sinatra and Mathis, he is rebuked as ‘sick’.)
And yet, one might argue Sinatra-ism won out over Elvis-ism. Once the novelty(and shock value) of Rock n Roll wore off, what was there but professionalism? Indeed, Elvis Presley himself abandoned his earlier style and morphed into a performer much like Sinatra. He became a Las Vegas act. One might even say Sinatra-ism won out over Dylan-ism. Bob Dylan was the greatest artist of Rock, but once the artistic well ran dry, again, what was left but professionalism? For good or ill, one of the biggest acts around is Adele who is above all a professional.
There was clearly an ethnic angle to the Sinatra phenomenon. It’s usually the case that kids from underprivileged backgrounds try their luck in sports and entertainment. Italian-Americans, who lagged other white ethnic groups, were over-represented in sports and music. There was Joe DiMaggio in baseball. Rocky Marciano and Jake LaMotta in boxing. And lots of singers. But, the Italian-American role in Popular Music may also have owed to a rich cultural heritage. Italians had opera and lots of colorful folk tunes, though a lot of this got watered down for Anglo-American tastes(like what Chef Boyardee is to Italian Cooking). Paradoxically, precisely because the Italians were so rich in musical heritage, they may have missed the boat, relatively speaking, in the boomer Sixties given to novelty and experimentalism. To some degree, this was also true of blacks. Though blacks played a huge role in 60s musical culture, they were overshadowed in the second half of the decade in terms of innovation and originality. Blacks, awfully proud of their own styles, mostly stuck to soulful or bluesy standards while White Rock pushed the envelope into new amazing directions, with additional inspirations from surprising sources, even Hindu music. During this period, Jimi Hendrix and Arthur Lee(of Love) were outliers. Indeed, Ellen Willis the female rock critic described Hendrix’s output as part of ‘White Rock’. In contrast, the British, not known for a great musical heritage, eagerly adopted whatever seemed exciting and ran with it, producing the revolutionary sounds of the Beatles, Rolling Stones, the Who, Pink Floyd, the Kinks, and others. And Led Zeppelin combined hard blues with Wagnerian operatics. Without much of a musical pride of their own, the Brits took to the new frontier with passion. Those without spices of their own are more likely to try new spices. No wonder Anglos suddenly became the biggest ‘foodies’ around the world.
Perhaps, Italian-Americans felt they had an excess of musical culture/color. Also, the Italian style was more complementary with Jazz, a combo of brass, sass, and class. Though Jazz culture could be lurid and kinky, it was also about dressing well and looking stylish, thus appealing to Italian-Americans. (In MEAN STREETS, even lowlife street hoods wear proper attire.) Italian-American community may have leaned Democratic and politically liberal but remained culturally conservative, with greater emphasis on family, clan, and community. And the Church. So, the Rock Culture that defined the boomer generation could be a turn-off. Even the Rascals, perhaps the best Italian-American rock band of the Sixties, had more of a sentimental attachment to established musical genres. Their best song, “How Can I Be Sure” has an Old World flavor.
Rock n Roll may have been more amenable to Italian-American culture. Though low and crass, its aggression made for tribal mentality, the kind in WEST SIDE STORY. So, even if Rock n Rollers didn’t mean their music to be street gang music, it went well with leather jackets and switch blades. The Jets vs the Sharks.
Rock Culture, in contrast, was about love and peace(even as some of the music got louder and crazier). The new tribalism was really an anti-tribalism, about flower power and grass than fists and turf. No wonder the Rock n Roll kid in I WANNA HOLD YOUR HAND(Robert Zemeckis comedy about the arrival of Beatlemania in America) hates the Fab Four whose joyousness negate the machismo of Rock n Roll. And THE WANDERERS(directed by Philip Kaufman) ends with an Italian-American kid in the early Sixties ruefully gazing at the dawning of the Folk Music scene(that would have a profound impact on Counterculture).
Not that Frank Sinatra was about tribal hostility. Politically, he went out of his way to oppose racial discrimination against blacks. In Hollywood, he made a not-very-good but rather surprising WWII movie that treated Japanese soldiers with a degree of sympathy: NONE BUT THE BRAVE.
Still, Sinatra wouldn’t have been nothing without distinctions. The private life was not to be confused with the public life. There was professionalism and amateurism. One had to dress for the occasion. The stars took the stage or screen, and the audience remained in the seats. (To be sure, during the height of Sinatra-mania, a harbinger of bigger manias to come, things did get out of control with the girls.) The Italian-American community was more prone to feeling that way. Italian-Americans had more a culture of respect for the elders, cultural if not always familial. If the likes of Sinatra and Dean Martin set the standards, those were ones worthy of emulation. (If Dean Martin seems somewhat out of place in RIO BRAVO, it has less to do with his Italian-ness than his plain cowboy clothes. It was Sergio Leone and the Spaghetti Westerns that really added style to the Western genre.) Martin Scorsese once remarked that Sixties culture was so different from the Italian-American community he knew. His ethnic enclave was, at the time, insular and indifferent to vast socio-cultural changes happening all around. Later, when an Italian-American became the prominent face of popular music, it was John Travolta in SATURDAY NIGHT FEVER. Though disco was hardly Italian-ish, it was about dressing up and spending inordinate amount of time on one’s hair.
Though hardly a fan of Sinatra, what he stands for has special meaning for me on account of two movies. Indeed, these two movies illustrate the special standing Sinatra has in American Cultural History despite the profound changes stemming from the boomer era. These are not the well-known Sinatra movies like FROM HERE TO ETERNITY or THE MANCHURIAN CANDIDATE, or one of the several musicals he made. Rather, Sinatra-ism stands out in precisely because the films are about the world in the process of boomer transformation.
The first is BABY IT’S YOU(story by Amy Robinson), the only truly great film by John Sayles, an intelligent director who marred most of his works with nods to social significance. Who the hell wants do-goody Peter-Seegerism in movies? BABY IT’S YOU is the exception and may well be, along with DINER, the best movie about young people in the 1980s. John Hughes dominated the youth movie market in the 1980s by pandering to the lowest common denominator, but the decade’s two best movies about youth are set in late 50s and mid-60s and based on personal memories. BABY IT’S YOU is about Jill, an upper-middle-class Jewish student majoring in drama. She’s headed to some elite college full of Wasps and Jewish girls from affluent families like her own, but in her final year of high school, attracts the attention of some Italian-American guy know as the ‘Sheik'(like Rudolph Valentino). While the times are changing, the guy is resolutely old school when it comes to dress, hair(oily), and style. In contrast, Jill is attuned to the newest trends in the arts and culture. She wants to fit in with the Zeitgeist.
It all comes to a head when both their illusions go up in smoke. He was so infatuated with instant stardom that he never realized that success owes to natural talent + hard work + luck. It doesn’t just fall at your feet because you dress well and have high self-esteem. He thought he’d become a star in music even though he can’t sing because he’s got the looks and is liked by tourists in sunny Florida. It never seems to have occurred to him that Sinatra had real talent and worked extremely hard at it, not least because he wasn’t so hot in the looks department. Without musical talent, would Sinatra have made it in the movies or been noticed by women?
As for Jill, she saw herself as leaving behind her humdrum middle class milieu and seeking authenticity as an artist, but she’s overly sensitive to peer perception and follows every new trend. They meet again, probably for the last time, in their painful moments of self-realization. Still, before they bid farewell and go separate ways, they share a final moment on the college dance floor. Though a psychedelic band plays the gig, they take his ‘weird'(because ‘square’) request to play “Strangers in the Night” by Sinatra. Other students, who’d been rocking to the latest music, seem bemused but slowly ease into the mood of Ole Blue Eyes.
The final part of BABY IT’S YOU could be a corrective realism to THE GRADUATE, actually a fantasy. Benjamin manages a fairytale ending as he runs off with Elaine Robinson, but there is no pie in the sky for Jill and the Sheik. And that everyone begins to dance to Sinatra, their parents’ music, is suggestive of what Mike Nichols said about the two elopers: They will end up like their parents.
The meanings are threefold. For the Italian-American Sheik, it’s his final gift to the girl. He’s back in the image that caught her eye in the first place, in high school where, unlike the other boys, he dressed in style and moved with confidence. For her, he plays that role one more time. But, it is also what he will always be. Despite the loss of illusion — he’s not cut out for stardom — and a future like his old man’s(blue collar work), he can always take pride in looking good and dressing well. In a way, this was Sinatra’s gift to the men of his generation. At the very least, no matter however humdrum their station in life, they could look a bit classy by taking pointers from men like Sinatra.
For Jill, the song speaks a timeless truth. At every moment in her life, she met boys and girls with whom she thought she’d bond forever, but ultimately, they are all like strangers in the night, especially in modern and mobile America. Just like she drifted apart from her high school friends, she will forget her college friends. And even though, for a time, she fell for the Sheik as the love of her life, they are incompatible in so many ways and must go separate ways. The Counterculture said the Moment is everything. Summer of Love will change the world and what’s happening now is what really matters. In contrast, “Strangers in the Night” is resigned to the timeless truth that life goes on, strangers become lovers, lovers become strangers. The song was both reassuringly old in style and a departure for Sinatra. In its air of alienation and detachment, it could even be ‘cool’ and ‘hip’ by the standards of the day. Not quite 007 but the new face of Sinatra who, unlike many of his peers, was capable of change, walking the fine line between nostalgia and fashion. It’s also a song that only an aged voice could have pulled off.
The other memorable Boomer/Sinatra moment is in LOST IN AMERICA. The movie has a contemporaneous setting. It’s the yuppie eighties, and David Howard(Albert Brooks, who also wrote and directed) is a thoroughly status-and-material-obsessed professional in advertising. But when denied the promotion he’d been dreaming of, he decides to give a big middle finger to upper class aspirations. Ironically, it’s not because he’s put off by excess materialism but because his ascendancy isn’t fast enough. His principled stance is the perverse product of his thwarted ambition.
As a ‘bold’ gesture to prove to the world and himself that he’s no longer in the rat race, he embarks on a late-blooming quest to search for America, what the guys supposedly did in EASY RIDER. The first notable song in the movie as he and his wife drive out of the city in a Winnebago is the 60s rocker “Born to be Wild” by Steppenwolf. But these two, who ostensibly want to ‘touch Indians’, decide to spend a night in Las Vegas where the wife, in a fit of wild abandon, gambles away all their ‘nest egg’. Of course, Las Vegas is more Sinatra-ville than Hippie-stan. (The Sixties became associated with great events, like Woodstock. But events come and go, whereas industries like Las Vegas remain.) And, what can be more crass and materialistic than gambling? And yet, her loss of inhibition could be regarded an expression of the Sixties spirit. After all, the message of Counterculture was to liberate yourself from traditional notions of responsibility and do what comes naturally. And so, the couple is faced with a conundrum. She acted ‘liberated’ and, as a result, lost all their money to Big Capital, the enemy. In contrast, he insisted on prudence so as to maintain the conceit of their ‘liberation’. Indeed, he is later forced to admit that the guys in EASY RIDER could pull it off only because they were, after all, supply-and-demand capitalists who sold drugs and stashed away the cash in a safe place.
But without the nest egg and without high-paying jobs, Howard decides to make the best of it… that is until, in the role as school crossing-guard, he gazes at a Mercedes Benz(with seats of leather apparently, perhaps a warped allusion to the Holocaust and human lamp-shades). Then and there, all the illusions vanish into the air, and the couple is driving across America to none other than the Big Apple to Sinatra’s rendition of “New York, New York”, which like “Strangers in the Night” was both old school and relatively new(as the song came out only in 1977 with the release of Martin Scorsese’s movie).
All this reminds me of a scene in Oliver Stone’s NIXON. It’s near the very end when Anthony Hopkin’s Nixon, upon signing the letter of resignation, finds himself alone with the portrait of JFK. He mutters, “When they look at you, they see what they want to be. When they look at me, they see what they are.” With the passage of years, the generation that wanted to regard themselves as the messianic John Lennon of “Imagine” ended up more like Frank Sinatra. Now, any comparison of Sinatra and Nixon may seem absurd as Sinatra was a big star whereas Nixon was considered unpleasant in look and style. Yet, Sinatra’s stardom was somewhat unlikely because he really didn’t look that good. Apart from his success in singing, his stardom owed to luck and connections. He played the game and was tainted by corruption.
In a way, it’s difficult to imagine a cultural figure as multi-faceted and multi-involved as Sinatra, especially when compared with the big stars of the Sixties. Among boomer youth, there was a saying, “Don’t trust anyone over thirty”. That meant, ideally at any rate, the Rock artists shouldn’t involve themselves too closely with business. They should just make personal music. (Or engage in business in a utopian manner, like the Beatles with Apple Corp after Brian Epstein’s death; it turned into one big fiasco. Another ideal was to put on free concerts, like the Rolling Stones at Altamont. Another fiasco.) Also, even if boomers were politically engaged, the ideal was to remain clear of the bastions of power and privilege. Protest against the Man, don’t be part of the Man’s structure(until Saul Alinsky advised otherwise).
As such, many of the key musical figures of the Rock Era had limited involvement with the real world. In contrast, Sinatra was engaged in many areas. Not only did he make it in music but he became a movie star. He was also associated with gangsters who reputedly helped his career a few times, which became the basis of Johnny Fontaine in THE GODFATHER, another reminder of what the boomers really became. He also played the role of middleman between the mafia and politicians. Though he came to prominence in more ‘innocent’ times(before the crazy Sixties) — it’s as if US went from less innocence to more naivete —, he was more comfortable with compromise and corruption as ways of the world. Yet, despite all this, he too fell under the illusion that he was on the side of angels because he supported the right causes(such as Civil Rights) and became close with Mr. Camelot John F. Kennedy. His sins would be washed away with the right connections. But then, the Kennedy brothers turned against the mafia(that had helped rig the election), and Sinatra found himself on the outside. It wasn’t long before he was supporting Ronald Reagan as governor and Nixon for president. He had truly become the Chairman of the Board. He also got entangled with the likes of Mia Farrow.
Boomer hippies romanticized about going back to nature, as if Fountain of Youth was waiting for them in the New Eden of Woodstock. After three days, Woodstock became a disaster zone. And, eking out a living from trees and dirt was no cakewalk. In the end, real potential was in the cities that Sinatra sang about: Chicago, his kind of town, and San Francisco, where he left his heart. And of course, New York, to which Albert Brooks is headed in LOST IN AMERICA. Blacks sure gained more from moving to cities than American Indians did by remaining in rural reservations.
Sinatra’s signature song was perhaps “My Way”, which is loaded with the contradiction that, to do it your way, you must join the company. Boomer ideal was to be personal, authentic, true to oneself without compromise. But just about all boomers who ended up doing anything became the suits. Perhaps a timeless truth about the nature of power, one which the boomers thought they could finally cast aside, only to end up, like Albert Brooks in LOST IN AMERICA, discovering the Real America by heading back to the city with high rises, high-paying jobs, and connections that matter. George Lucas built an empire independent of Hollywood and did it his way… only to churn out very Hollywood-ish movies playing to age-old conventions of pleasing the crowd. And he sold his personal dream to Disney.
One of the reasons Sinatra fell out of favor in the Sixties was that, despite his political credentials of being a good progressive, he had ties to the mafia. This didn’t jibe well with the New Frontier thinking of the Kennedy era and beyond. And yet, fast forward to today, and the Power Boomers no longer need to be associated with the mafia because they are gangsters or gangstoids themselves. In a way, Michael Corleone was naive about going legitimate and turning away from organized crime. There’s a better way: Legalize the criminal vices, and all that was once illegit becomes legit. Just like that. With gambling legalized just about everywhere, we are living in Sinatrapolis. And given the state of US foreign policy as dictated by Jewish boomers, the old mafia seem like small potatoes, hopeless amateurs. In 2020, the system cynically employed black thugs and Antifa to burn down cities just to gain a few percentage points in the black vote and to embarrass Trump. And Big Pharma has proven to be a global-gangster operation under the Covid Regimen: They made the world an offer it can’t refuse.
And yet, triumphalism isn’t what Sinatra-ism is about. Even in the song, “My Way”, there is a note of melancholy and resignation as well as pride and defiance. It’s not about a man who always got to do things his way and feels exultant. Rather, it has the sound of man who betrayed or abandoned so many dreams but still managed to make it to the finish line and keep something to call his own. It’s more a song of survival than victory. And especially his later songs are more about the mood after-the-party than during it. A sense that no matter how intense the moment, it will burn out and lights will dim and life will go on as it always has. That is the beauty and sadness of BABY IT’S YOU’s final moment, and maybe a saving grace for the boomers as well.