FRANK: The Making of a Legend by James Kaplan

by John Boland

Dolly Sinatra was a tough woman. A midwife and a back-street abortionist – nicknamed “Hatpin Dolly” and twice arrested for the latter activity – she was a formidable figure both as a mini-Mafia figure in her rough-and-tumble New Jersey neighbourhood and also in the confines of her home, where she inflicted hard love on her only child, dressing him in Little Lord Fauntleroy outfits while beating him with a stick.

As he grew up, his mangled left ear and the scars on the right side of his face were a constant reminder of the brutal forceps delivery that brought him into the world, while his mother’s volatile approach to parenting adversely affected him, too. “She scared the shit outta me,” he told Shirley MacLaine decades later. “I never knew what she’d hate that I’d do.”

Mothers of troubled geniuses often have a lot to answer for and James Kaplan, in this latest of many biographies of America’s greatest singer, sees Dolly as a key influence on her son’s life, not least in his attitude towards women in general. Or, as Kaplan puts it, this “only child, both spoiled and neglected, praised to the skies and viciously cut down when he fails to please, grows up suffering an infinite neediness, an inability to be alone, and cycles of grandiosity and bottomless depression.”

Success apparently did little to lessen the effects of the maternal upbringing – we’re told of the “loud-talking bantamweight who snarls to hide his terrors” and of  the man with “the rage of a child who is terrified he will be slapped down.” And Dolly’s influence, Kaplan argues, also determined later friendships with similarly affected males.

He was drawn to Peter Lawford because “both had overbearing mothers, both had minor physical deformities, both were beguiling and sexually voracious.” And then there was Nelson Riddle, whose inspired musical arrangements would revitalise the singer’s career in the 1950s and who, like Sinatra, was “the only child of a domineering mother and a weak father, a man with powerful sexual urges and a fondness for alcohol.” And in between, compensating for weak father Marty, he found the authoritarian males he desired in bandleaders Harry James and Tommy Dorcey, whose formative role as parental substitutes Kaplan dwells on.

This pop psychologising is all very well as far as it goes, but it brings us no closer to the man than previous profiles. Indeed, you get a much better sense of Sinatra  the person from Pete Hamill’s modestly intended Why Sinatra Matters, not least because Hamill was personally acquainted with him, as well as being a much more elegant and persuasive writer than Kaplan.

Indeed, for all the new book’s length (almost 800 pages), meticulous research and obvious enthusiasm, Kaplan tells us nothing that wasn’t previously known, while his recurring fanciful imaginings of private moments – the singer’s feelings on first meeting Ava Gardner, for instance – belong in a work of fiction.

And though he relates the narrative engagingly and weighs the evidence judiciously on such vexed matters as the break-up with first wife Nancy, the tortuous and doomed relationships with Gardner, and the ongoing dalliance with Mob figures, he has a tin ear for what’s most important of all – Sinatra’s musical genius.

It doesn’t help that, for unexplained reasons, the biographer ends his book with his subject’s winning of the 1954 supporting actor Oscar for From Here to Eternity. Yes, it was a watershed moment in his public rehabilitation after a decade in the doldrums, but Sinatra’s greatest years – the famed Capitol years in which he ensured his immortality – were still to come.

In these years, he and Nelson Riddle (and,  if less crucially, Gordon Jenkins and Billy May), redefined the art of popular song – indeed, the standards by which the singing of such songs would come to be judged. The vocalist’s baritone had deepened and darkened, the phrasing had acquired an exhilarating precision, there was a profound new awareness of the emotional possibilities of a song’s lyrics, and there were arrangers on hand capable of ensuring that these extraordinary attributes had an instrumental backdrop that was worthy of them.

And because of this coming together of unique talents – but chiefly because of the singer himself – music lovers throughout the world have access to Songs for Young Lovers, In the Wee Small Hours, Songs for Swingin’ Lovers, Come Fly With Me, Close to You, A Swingin’ Affair, Where Are You, Only the Lonely, No One Cares and Nice ‘n’ Easy.

Along with Billie Holiday’s 1930s Teddy Wilson sessions and Ella Fitzgerald’s Songbook series, these are the ten albums – all recorded within seven years – by which one recognises greatness in the interpretation of popular song, but Kaplan’s book alludes to only the first of them.

Maybe (though he doesn’t say so) there’s a second volume on the way which will document their making, as well as the Rat Pack era, the years with Reprise, the later marriages, and the endless touring that only stopped not long before the singer’s death twelve years ago. If so, perhaps the author will reveal himself to be as enthralled by the timeless and incomparable art as by the transient and often tawdry life.


“If I’d had as many love affairs as you’ve given me credit for,” Frank Sinatra famously told reporters, “I’d now be speaking to you from a jar in Harvard Medical School.”

Whatever the truth, he wasn’t lacking in sexual equipment. Ava Gardner was said to have enthused that “there’s only ten pounds of Frank, but there’s a hundred and ten pounds of cock.” Kaplan’s biography elaborates, citing the singer’s valet, George Jacobs, who revealed that his master had to have special underwear made to keep it in check.

And Kaplan, who maintains that the singer was “ambivalent” about his well-endowed frame, adds that the underwear “was a cosmetic as well as a physical accommodation. Sinatra didn’t want to attract undue attention while wearing close-cut tuxedo trousers.”

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