From the Vault: “The Guilt of Frank Sinatra”

As the tributes to Frank Sinatra in his centennial year continue – including tonight and tomorrow’s night Austin Symphony concert My Sinatra with Cary Hoffman – we couldn’t help jumping on the bandwagon and dusting off a favorite piece from Michael Ventura, who retired his Letters at 3AM column just over a year ago.

Ventura named his 1996 detective novel The Death of Frank Sinatra; when the actual death of Frank Sinatra happened in 1998, Ventura wrote a column titled “The Guilt of Frank Sinatra.” We’ve reprinted it in full below, along with the original illustration by Jason Stout (now the Chronicle’s creative director). When you’re done with that, we heartily recommend you head over to This American Life to hear Ventura read a mesmerizing excerpt from his novel. – Kimberley Jones

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It is now some days since the death of Frank Sinatra. The frenzy of hyperbole is done. Who was he singing to? "To me," many of us felt. Often it seemed he was singing in our place – voicing us. In the sphere of Tin Pan Alley music, with its peculiar mix of the suave and the desperate, the urbane and the romantic; a music of smooth, jazz-inflected melodies; a music in which the very slickness of the lyrics demands subtle and intensely personal phrasing, or the tune collapses into triteness; a music with precise rhymes that, to be effective, require equally precise diction; a music that must be acted as well as sung in order to be fulfilled – in that music only Ella Fitzgerald and Billie Holiday were his equals. (Sinatra always credited Holiday as the prime influence on his mature style.) The controversies of his life and the patina of his stardom will fade; his music won't. But music is not his entire artistic legacy. Sinatra was also an actor. And he told a secret about himself in his acting, a raw and guilty secret. His songs have a way of resolving that lets the listener imagine the whole tale has been told. But often Sinatra chose films in which the ending smashes the meaning, the entire world, of the characters. Yes, there were silly movies, too; but again and again he made strangely tense, bleak pictures that, when seen as the personal projects they were, tell a story of Sinatra that went unmentioned in his eulogies.

That story begins with From Here to Eternity, which won Sinatra an Academy Award in 1953. At 38 he was a has-been. His marriage with Ava Gardner was foundering, no one was buying his records, his last movies had been flops. He offered to do Eternity for nothing. Begged, connived; maybe even used the Mafia's influence. He said he was Maggio, the little irrepressible and, most importantly, doomed, wop. (I'm Sicilian, too, so I can say "wop" – but any real wop fights when called a wop.) Sinatra's Maggio gets thrown into prison, but his pride is still defiant. He hasn't got a prayer. A brutal sergeant beats him to death.

Obviously, something in Frank Sinatra didn't feel much like a swinger, or he would not have identified so intensely with Maggio.

After that role, Sinatra called his own shots as actor. He did only films that, for better or worse, he really wanted to do. That's the telling fact.

Considering where Sinatra was in his life in 1953, maybe Sinatra's identification with Maggio was understandable. But after 1953, Sinatra knew nothing but fantastic success. So why did he choose these films?

The Man With the Golden Arm, 1956. Sinatra's romantic albums are now wildly popular, his swinging image is secure, but he chooses to play a desperate dope addict. A man hypersensitive to any real or imagined slight, any hint of humiliation, in his daily life, playing a character who endures the gruesome humiliations of addiction and withdrawal – the opposite of his carefully honed image. Nobody takes on such a role just to show off – especially a Sinatra, who had so many other opportunities to show off. An artist takes a role like this to confess and express. Art is always part expiation. He had to have felt profound humiliation in order to act so convincingly; had to need to expose this in public. Had to show that he harbored a horror deeper than mere failed romanticism.

The Joker Is Wild, 1957. He plays a singer who stands up to the Mob and gets his throat slashed. He doesn't die and he doesn't rat. Becomes a stand-up comic instead. And a drunk. A nasty drunk. He loses the love of his life and winds up alone. The end.

Some Came Running, 1958. He's a vet, a drifter, a gambler, a guy from the other side of the tracks, a failed writer. He goes to his hometown, gets into fights, causes scandals, falls in love with two women, finally finds a real friend. The woman he marries catches a bullet for him and dies. The other woman, an aristocratic college professor, hates his way of life. His new friend develops a deadly disease. He may or may not write again. The end.

Ocean's Eleven, 1960. The wild Rat Pack-in-Vegas movie. Exuberant, yes, but after they rob the casinos they lose all the money, their identity is discovered, the song that plays over the last scene says, "Some judge is gonna say I'm puttin' you away," the Rat Pack walks out of frame dejected and defeated. The end.

The Manchurian Candidate, 1962. An intellectual Army officer. Brainwashed in Korea. Suffering the shakes, nervous breakdowns. He uncovers a heinous plot to kill a presidential candidate. There are murders right and left that he fails to stop. Incest is at the heart of the plot. He foils the evil scheme, but he has looked into the face of horror, and his expression on his last closeup tells us that he'll never recover, not really. He's won the battle, even the war, but he will never again believe that anything is what it seems. The end.

The Naked Runner, 1967. A World War II vet, now a successful businessman. British intelligence cons him, by successive sinister steps, and he never catches on. He is used mercilessly. Forced to commit an assassination for them. His last line in the film eerily echoes Lee Harvey Oswald's "I'm the patsy." The line is: "All a setup. I was set up." He's completely broken, utterly violated. All his life he'll have to live with this inner rape. He's carried off-camera too shaken to walk unaided. The end.

The Detective, 1968. He's an ambitious New York cop. He solves a headline murder – by sending the wrong man to the chair. "I saw the chance for a promotion," is his explanation at the end. In the process he discovers a scheme linking the Mob and the city's elite. He tries to expose this, but it's clear that the big crimes will go unpunished while the little criminals get arrested. "I saw things that terrified me," his character says, "and I thought I was above them – but I wasn't." He resigns from the job he loves. His marriage is kaput. (Plus: His wife, played by Lee Remick, is a nymphomaniac, the most sympathetic ever on film. He's totally humiliated by not being able to hold on to her.) Everything he's attempted and loved is lost. He drives off into the darkness. The end.

Contract on Cherry Street, 1977. He's a New York cop again. Head of a squad of detectives, all of them his friends, assigned by the mayor to bust the Mob. But it's only for publicity's sake. No one wants him to succeed. Again, the city's elite is in league with the Mob. "There's no law for these people. They make their own laws." His squad, his friends, go bad. They start committing murders. Everything and everyone he's believed in goes to shit. He tries to stop his own squad from murdering. Gets killed for his trouble. The end.

The First Deadly Sin, 1980. Frank Sinatra is 65 years old. His fortune, his rep, his legend, his legacy, is secure. He is supposedly happily married. He's been singing "My Way" for more than a decade. As has been true for 27 years, he can make any film he wants. This will be his last dramatic role. So what story does he choose? Well... he's a New York cop yet again. His wife is dying of kidney cancer. There's a serial killer on the loose. He knows who the killer is, but doesn't have enough proof. The killer is affluent and respected, can get the best lawyers, beat the rap. Jettisoning the code he's lived by all his life, Sinatra's cop murders the killer. Then he types up a confession, and hands in his badge. He leaves the confession for his captain to find in the morning. Tells the desk sergeant he's leaving the job. "It won't be the same without you." "It's always the same," answers Sinatra. Then he goes to sit by his wife while she dies. He breaks down crying, nestles his head on her dead shoulder. The end.

Given these consistent themes across a span of nearly 30 years, it's safe to say that Frank Sinatra was trying to tell us something, something that nobody was writing songs about – nobody except maybe Kurt Cobain and Bob Dylan, but not songs in Sinatra's style. His romantic music and silly comedies aside, the acting role he not only always returned to but insisted on, amounted to a hide-in-plain-sight compulsive confession. For who else has made such a string of bleak, hopeless cinematic statements? After all, these aren't the films of a Swedish or French existentialist; this is the American mainstream superstar. Frank Sinatra was trying to tell us why he had so much trouble sleeping.

"I'm for whatever gets you through the night," he'd once said, "be it booze or religion." It was usually booze. He often confessed that his nights were terrible. And why wouldn't they be? He'd known the inner circles of mobsters and politicians. How things really worked. What made America tick. And he'd profited from it. He'd seen himself as a monster in an elite of monsters, as well as a lover and a star. "I saw things that terrified me, and I thought I was above them – but I wasn't." His guilt humiliated him. He was humiliated not by the world but by the truth he'd seen – seen, but had been powerless to resist. And he had to get the word out somehow. To admit without admitting. To confess his horror and complicity without having to do penance for his confession. He was going to beat the rap, while he lived. But he was going to leave a clue. His honesty, such as it was, demanded this of him. Like the song says, "What is a man? What has he got?"