By Brian Turk
By Drew AIles
By Taylor Boylston
By Bree Davies
By Emerald O'Brien
By Gina Tron
By Jon Solomon
In point of fact, "My Way" doesn't stack up to the finest compositions on which Sinatra placed his stamp over the course of his long and fruitful career: It's fairly clunky and lacks the thematic subtlety he was so masterful at reflecting. However, Sinatra realized that the tune would resonate with those aficionados whose lives had been bound with his for as long as they could remember. He was hardly on his last legs on December 30, 1968, when he first recorded "My Way"; he still had nearly three decades left to him. But he'd long been drawn to romantic fatalism--back in 1959, when he was among the most popular men in the country, he'd released a moody LP boldly titled No One Cares--and he correctly guessed that in his hands, the offering's last-stand structure would come across like autobiography of a very cocky, heroic kind. In other words, he had a strikingly objective handle on his persona, and he understood that by taking advantage of his personal history, he could make "My Way" work. And work it did.
Given the plethora of intriguing characteristics that came together in Sinatra, it's to be expected that comparatively few observers have commented upon his self-knowledge. But this attribute as much as any accounted for his ability to ride the tides of changing fashion for well over a half-century of public life. In each era, he was able to look with cool detachment at his virtues and at the times themselves, and again and again he made them work together. There were periods in which the fit was a bit awkward: He never quite came to grips with rock and roll, his cover of George Harrison's "Something" notwithstanding, and when he tried to look country by dressing in denim, he seemed as uncomfortable as Richard Nixon hugging Sammy Davis Jr. But what's more remarkable than his stumbles are the triumphs he enjoyed during the September of his years. The Seventies saw his "Ol' Blue Eyes Is Back" return and the smashing breakthrough of "Theme From New York, New York," arguably the all-time karaoke classic. During the Eighties he was a top concert draw thanks to tours with Davis, Dean Martin and Liza Minnelli. And the Nineties were highlighted by two volumes issued under the moniker Duets, both of which hit the Billboard Top 10. The albums were generally dreadful as a result of their bloodless concept: Because Sinatra's partners sang along with pre-recorded tracks rather than interacting with him in person, the teamings exhibited all the spark and spontaneity of a corporate report. But the participants, who ranged from Lena Horne and Barbra Streisand to Gloria Estefan and U2's Bono, testified to his cross-generational appeal.
The entertainers on Duets obviously believed that associating with the Chairman of the Board would enhance their reputations. Likewise, Sinatra went into the project hoping to receive a much-needed boost; the reviews of his early-Nineties concerts had noted his forgetfulness, his sloppiness and the fraying of his once-impeccable delivery. But he needn't have worried that the public's affection for him was waning. At the 1994 Grammy Awards ceremony, the speech he gave while accepting a lifetime achievement prize was so rambling and disconnected that his own staffers requested that the orchestra at his feet cut him off. But instead of applauding the producers of the broadcast for acquiescing, fans were aghast at the rudeness of the decision. After all, this wasn't just any long-winded celebrity. This was Frank Sinatra, and if he wanted to babble incoherently before a mammoth global audience, then that's precisely what he should have been allowed to do.
Over and over, Sinatra proved immune to the sorts of public-relations disasters that regularly caused others' stars to dim. A case in point was His Way, author Kitty Kelley's muckraking 1986 expose of his darker side. Much of the information catalogued in the tome, which followed Sinatra from his birth in Hoboken, New Jersey, to his allegedly more-than-casual relationship with First Lady Nancy Reagan, was far from flattering. Dolly Sinatra, Frank's mother, was portrayed as a freelance abortionist who initially dressed her only child in pink because she had been hoping for a girl. Her husband, Marty, came across as a Milquetoast who followed Dolly's orders like the weakest private in the division. And Frank was cast as a tinpot Napoleon who littered his speech with profanities and racial epithets, slept with an astounding array of floozies and prostitutes and mistreated virtually everyone who came into contact with him; in one vivid episode, he is depicted as having thrown a gal pal through a plate-glass window.