Ten days after winning the Oscar for "From Here to Eternity," Frank Sinatra sat down and typed a note to a friend, clearly in response to a congratulatory letter or telegram. The note, on Paramount Pictures stationery and in Frank's customary, too-impatient-to-press-the-shift-key style, read:

april 5, 1954

dear lew --

my paisan mr sinatra is still on cloud nine and the bum refuses to come down . . .

That bum -- "mr sinatra" -- was so thrilled, the note continued (still all lowercase, still in the third person), that he was "ridiculous." And then, after a final thanks to the recipient, came the signature: "maggio."

It's a charming letter, and a fascinating one. Throughout his life, Sinatra employed secretaries who answered his voluminous mail, often signing his name themselves. From time to time, though, when the spirit moved him, he penned or typed his own missives, and the letters are him, revealing his restless intellect, his sense of humor (always more spontaneous in personal circumstances than on stage), even a literary sensibility. And why not? As a great singer he was a great storyteller; why should that faculty switch off when he was away from a microphone? In this note he is writing in character, as PFC Angelo Maggio, the role that won him that Academy Award, and the voice is perfect: "the bum refuses"; "he's so thrilled he is ridiculous." From the moment he'd first picked up James Jones's blockbuster novel, Sinatra had completely identified with Maggio, the feisty little private from Brooklyn who speaks in a kind of Damon Runyon-ese. He had campaigned, hard, for the movie role by barraging the filmmakers -- Columbia Pictures president Harry Cohn, producer Buddy Adler, director Fred Zinnemann, screenwriter Daniel Taradash -- with telegrams touting his perfect suitability for the part, and he had signed every wire just as he'd signed this note: "Maggio."

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Frank Sinatra had identified so powerfully with the character not only because Angelo Maggio was a skinny, street-wise Italian-American from Brooklyn -- like Sinatra's native Hoboken, close geographically to Manhattan but oh so far away -- but also because Maggio was one of the world's downtrodden, a little man who drank to ease his sorrows and spoke truth to power with wisecracks. When Sinatra first read "From Here to Eternity," in early 1951, he was feeling considerably downtrodden himself. His records were no longer selling; he was having vocal and financial problems; the I.R.S. was after him. He had become infamous, pilloried in newspapers across the U.S., after leaving his wife and three children for Ava Gardner. Metro-Goldwyn-Mayer had recently terminated his movie contract, and he would soon also be dumped by Columbia Records, as well as by his talent agency, the Music Corporation of America.

"He's a dead man," the talent agent Irving "Swifty" Lazar declared in 1952. "Even Jesus couldn't get resurrected in this town." Maybe not, but Frank Sinatra could. Literally overnight -- after the Academy Awards ceremony on March 25, 1954 -- Sinatra brought off the greatest comeback in show-business history. And he had done it all in Hollywood, a ruthlessly Darwinian company town that reviles losers but has the sappiest of soft spots for a happy ending. His Oscar underlined the fact that he was also a freshly viable recording artist with a new contract at Capitol Records, where he and a brilliant young arranger named Nelson Riddle had begun creating the string of groundbreaking recordings that would revolutionize popular music in the 1950s.

And quite suddenly that spring, without a shred of embarrassment about its fickleness, the entire entertainment industry began throwing itself at his feet. "The whole world is changing for Frank Sinatra," Louella Parsons wrote in her syndicated column of April 19th. "Today he has so many jobs offered him he can pick and choose."

Parsons was talking about movies, although television, radio, and nightclubs were also calling. Among the film possibilities offered to Sinatra: a supporting part alongside the hot-as-a-pistol young Robert Mitchum in the medical melodrama "Not As a Stranger"; the second lead in a Warner Bros. remake of "Four Daughters," the picture that had catapulted John Garfield to fame; a co-starring role alongside Marilyn Monroe in the Twentieth Century-Fox musical "Pink Tights," even though Marilyn Monroe soon dropped out when she heard how much more the studio was offering Sinatra than her. And lo and behold, MGM -- where Louis B. Mayer had personally fired Sinatra in 1950 after he made an impolitic joke about Mayer's mistress (and where Mayer himself was now history) -- wanted him back, for the long-discussed "St. Louis Woman," alongside Ava Gardner.

This was distinctly problematic for several reasons. For one thing, Gardner, who'd been outraged that Metro had dubbed a professional singer's voice over hers in "Show Boat," was determined never to make another musical. For another, she had come to hate Hollywood with a passion. She was living as an expatriate, cohabiting in Spain with the charismatic and brilliant bullfighter Luis Miguel Dominguin, the darkly handsome torero whose rivalry with his brother-in-law Antonio Ordoñez would later inspire Ernest Hemingway's long Life Magazine piece "The Dangerous Summer." Most important of all, however, she was about to file for divorce from Frank.

Excerpted from "Sinatra: The Chairman" by James Kaplan. Copyright © 2015 by James Kaplan. Excerpted by permission of Doubleday, a division of Penguin Random House Inc. All rights reserved. No part of this excerpt may be reproduced or reprinted without permission in writing from the publisher.