Frank Sinatra’s character flaw isn’t hard to name. He lived in daily fear of humiliation. Photograph by William Gottlieb / Redferns / Getty

Having come out of the closet, or the casino, not long ago, as an unqualified Frank Sinatra idolater, I approached the second volume of James Kaplan’s biography of the singer (“Sinatra: The Chairman”) with what our critical mothers and fathers would have called immense trepidation, since the book would have to deal not just with the great man’s best records but with his messy entanglement with the mob and his sad, stultified later years. (I saw him perform once, toward the very end, at Madison Square Garden, and it was like seeing the dead El Cid mounted on his horse to lead the Spanish Army: noble but undeniably stiff.)

Kaplan’s book turns out to be, to continue in the old reviewers’ language, hugely readable, vastly entertaining, a page-turner, and all the rest. But it’s also interesting as a fine instance of a strikingly newish kind of thing: the serious and even scholarly biography of a much gossiped-over pop figure, where the old Kitty Kelley-style scandal-sheet bio is turned into a properly documented and footnoted study that nonetheless trades on, or at least doesn’t exclude, the sensational bits.

Peter Guralnick’s two-volume account of Elvis Presley was the pioneering model of the genre. Designed in some small part to defuse Albert Goldman’s ugly, contemptuous—but often insightful—biography of the King, Guralnick worked through the details of Elvis’s life with more studious patience than Leon Edel devoted to Henry James’s (Guralnick’s long endnote arguing through who actually worked the lathe on Elvis’s first recording, Sam Phillips or his assistant, is a stunner). Guralnick is a fan, and this was both good—he deeply loved Elvis, not just the Sun sessions, which everyone admires, but more ‘problematic’ material, too—and bad, because, in his earnest desire to show Elvis the American singer, he rather slighted Elvis the American icon, who (and Goldman was not wrong in this) enacted the role of self-made King in a kind of instinctive burlesque of all the ancient stereotypes of majesty, from the official mistress to the exotic “possession” of Hawaii. What was weird is that, in Guralnick’s book, Goldman’s more sensational gossip was, on the whole, quietly confirmed—Elvis was a junkie with occult preoccupations, who did die of an overdose, and was toured to death by “Colonel” Tom Parker, in part because Parker really was an illegal immigrant, from Holland, who couldn’t get a passport and was frightened to take Elvis abroad—while being simultaneously deprecated as inessential.

The ugly, scuttlebutt version of Elvis was, to put it bluntly, as a dumb fuck with a drug problem; Guralnick showed that he did have a drug problem, but was far from dumb, with keen spiritual yearnings that, through bad management and bad luck, got sidetracked into those grinding tours and substance abuse. The ugly, scuttlebutt version of Sinatra is as a bad guy with a big voice. Kaplan shows that the bad-guy stuff was, in truth, pretty bad, about as bad as one had imagined and a lot worse than one had hoped. He did hang out with and cultivate mobsters, real killers, though more in a semi-hostile, semi-affectionate fraternal manner than with the pitiful, feudal devotion pictured in “The Godfather.” (There seems to be no truth in the rumors that the mob bullied Harry Cohn into casting Sinatra in “From Here To Eternity,” not least because Cohn was plenty mobbed-up himself.)

Worse, Sinatra beat people up, or had others beat them up for him, often in shameful acts of bullying—picking on casino employees or less successful, dependent entertainers. (This happened to Shecky Greene, who emerges in the biography as a far more interesting and volatile man than one could have ever imagined, and, weirdly, to Jackie Mason, who had shots fired at him, apparently for dissing the Chairman.) Kaplan even offers veiled, worrying hints that Sinatra might have been implicated in an actual murder. (A man with whom he had an altercation was killed in a mysterious traffic accident a few weeks later.) These instances were sporadic and counterbalanced by his many acts of charity, some impulsive, and some systematic—touring for the benefit of children’s hospitals and the like.

Sinatra’s character flaw isn’t hard to name. He lived in daily fear of humiliation, and in its (often imagined) presence his temper tipped over in an instant. This was followed, usually, by remorse, once he had sobered up and stopped seeing red. But, in the interim, real damage was done to real people: he threw a telephone at a businessman once at the Beverly Hills Hotel, fracturing his skull and very nearly killing him. The other cause of his rage may be oddly taboo to tell. Sinatra was a bad, mean drunk, and, since he was often drunk, he was often bad and mean. (John Lennon was a bad, mean drunk, too, and when he got loose long enough to show it the author of “Imagine” and “Julia” could do similarly violent things.) Despite everything we ought to have learned, we still make a ballad out of alcohol. It was Jack on the rocks, not crack from a bag, and so we somehow think that it’s not so bad. The other sad truth Kaplan illustrates is that demons rage in the rich and famous as much as they do in the poor and unknown—and maybe rage still more, since, having defeated the usual demons of worldly failure that haunt the rest of us, the famous are left alone with the remaining, inexpungible ones, grinning up evilly at them from inside.

Kaplan is not a fan in quite the way that Guralnick was, but he is an unqualified admirer, and with better reason, since what there is to admire is not a handful of early records, but ten years of work, from 1954 to 1964, of astonishing accomplishment—the best uninterrupted session of interpretive singing ever offered by an American, becoming in the end the finest monument that the great American songwriters possess. Kaplan’s Sinatra was a violent guy—but he didn’t have a “big voice” like one of those operatic tenors with a voice so big that it has pushed everything else out of his skull. Sinatra, he shows, had an astonishing musical intelligence, of a subtlety and soulfulness still unequalled. He was a master of understatement and narrative so complete that he could still spellbind audiences after his voice had gone, and he was even more of a legend among other musicians than among his fans. Nor is Kaplan simply an idolater. He sees how genius sits in a fortunate network, offering character sketches of Sinatra’s arrangers, who were as essential to Sinatra’s art as George Martin’s production was to the Beatles. They’re captured as more than names: the saturnine Nelson Riddle, the last-minute genius Billy May, and the old-fashioned Gordon Jenkins, not to mention supporters as gifted and forgotten as Milt Bernhart, who played the indelible trombone solo on Riddle’s transformed version of Cole Porter’s “I’ve Got You Under My Skin.”

Shouldn’t this push aside the malicious gossip? Why does the other crap matter at all? It matters because if art and the lower reaches of journalism and biography converge on a single point of common purpose, it is in being truthful about human beings as they really are and not as we would have them be. History is what we have to struggle to remember even when legend is more pleasing. It would be nice if Sinatra had been a good guy with a few regrettable friendships rooted in Jersey simpatico—it was a lot worse than that. It would be nice if J.F.K. were a family man with a sometimes-wandering eye—the truth there, too, is more ravenous and complicated. None of this need diminish our admiration or even our love for them. Humanism is made from a faith in humans, as they actually are, flawed and real, screaming devilish threats at casino managers and then singing “Angel Eyes.”