Frank Sinatra

Can even Death stop Ol’ Blue Eyes?

Illustration by Philip Burke

Given the way the Grim Reaper has been picking off celebrities recently, Frank Sinatra should probably dry-clean his tux, polish his Guccis, and get ready for his limo ride to the Big Casino. The 81-year-old singer’s weak heart has sent him to the hospital twice in the past year, and there are rumors of Alzheimer’s disease and cancer. His children and current wife (No. 4), Barbara, are already feuding over who controls his empire, while networks, magazines, and newspapers have put the finishing touches on their Sinatra tributes.

Sinatra has always said that “dyin’ is a pain in the ass,” but it may not be so bad. Dying, as living, the Chairman of the Board is right where he’s always liked to be: at the center of attention. Unlike fellow crooners (notably MTV hunk Tony Bennett), Sinatra has transcended irony and avoided kitsch. Music critics and the record-buying public, who don’t agree about much, agree that Sinatra is the greatest popular singer in American history.

And, as the media report every few days, Sinatra is cool again. His 1993 Duets album–in which he sings his greatest hits with pop stars such as Luther Vandross and U2’s Bono (click here to hear Sinatra and Bono tackle “I’ve Got You Under My Skin”)–has sold 3 million copies in the United States, far more than any of his earlier recordings. The hit movie Swingers paid slavish tribute to Sinatra lounge culture. Recent articles in Vanity Fair and elsewhere have depicted Sinatra and the Rat Pack as the acme of American cool.

Sinatraism has become the house religion at men’s magazines such as Details and Esquire. Later this fall, Esquire writer Bill Zehme will release The Way You Wear Your Hat: Frank Sinatra and the Lost Art of Livin’ (his apostrophe), a 245-page guide to Frankness. Zehme instructs on swaggers, cocktails, $100 tips, street fights, and seductions. (All should be frequent.) This Sinatra is a Sinatra for the sleek, prosperous, cigar-swilling, martini-puffing ‘90s, a tonic for political correctness. His misogyny and promiscuity have been recast as healthy libido, his Mafia ties and thuggery as macho. He’s a man’s man. How could you not admire a fellow who bedded Lana Turner, Ava Gardner, Mia Farrow, Anita Ekberg, Marlene Dietrich, and Marilyn Monroe?

Illustration by Philip Burke

So Frank Sinatra is cool again. Well, Frank Sinatra has always been “cool again.” Sinatra rose and fell as a teen idol in the ‘40s, then returned to stardom in the early ‘50s. Between 1953 and the mid-’60s, he made his best records, scored most of his biggest Billboard hits, gave his finest film performances (The Manchurian Candidate and From Here to Eternity, for which he won an Academy Award), and exerted the greatest political and cultural influence. (Some particularly enthusiastic, daft Sinatra fans credit him with Kennedy’s 1960 election victory, claiming that Sinatra helped line up the Mob behind JFK.)

Since that peak, Sinatra nostalgia has been a cottage industry of American culture. Every few years, Sinatra is “rediscovered.” Sinatra himself doesn’t change; what changes is the way we choose to perceive him. He’s a national Rorschach test: America periodically concocts a new Sinatra to fit the Zeitgeist.

Consider Sinatra’s rebirth as “cool” in the early ‘70s. He came back as a Me Generation icon, the Rat Packer reincarnated as an individualist. His late ‘60s albums, dismissed as lame attempts to ape rock when they debuted, were now applauded for their courageous, free-spirit experimentalism. Critics harked back to his original popularity in the ‘40s, noting that Sinatra had helped to end the Big Band era and usher in the age of the individual star. His signature song, after all, was “My Way.” (Click here to hear him sing it.)

When punk broke in the late ‘70s, Sinatra was reborn again–this time as Proto-Punk, popular music’s first great rebel. Sinatra had been one of the first artists to start his own record label (Reprise, in 1961): This was recognized in the late ‘70s as proof of his artistic integrity and a kick in the smug face of corporate music. His brawling and boozing in the ‘50s presaged the punks’ brawling and boozing in the ‘70s. Even Sinatra’s Mob ties supposedly demonstrated his flouting of authority. The Sex Pistols’ Sid Vicious recorded “My Way,” a bizarre combination of homage and scorn.

Illustration by Philip Burke

His next incarnation: Reaganite. Through the ‘80s, Sinatra palled around with Ron, Nancy, and his usual crew of sycophants. The punk became Ol’ Blue Eyes. For Reaganites, Sinatra symbolized all that was once right about America (and would be again after a few years of supply-side economics): classy music, machismo, bonhomie, and good times. (The right’s embrace of Sinatra inspired the oddest chapter in the Sinatra cycle: a counterclaim by the left. The New Republic and others tried to redeem Sinatra for liberals, advertising his early support of civil rights, his assistance to black musicians before such help became fashionable, his opposition to McCarthyism, and his failed attempt to break the Hollywood Communist blacklist.)

There’s one other Sinatra phenomenon that keeps repeating itself: dirt. In the ‘60s and ‘70s, rumors of Sinatra’s Mob ties were family entertainment. In 1986, Kitty Kelley’s dishy biography, His Way, confirmed most of the nasty gossip about his love life. Later this month, Sinatra: Behind the Legend, a new warts-and-all (and-more-warts) biography, will hit bookstores. Author J. Randy Taraborrelli has been somewhat cagey, but early reports suggest that the book will be full of salacious details about Frank’s seven-year affair with Monroe, other extracurricular activities, and an aborted Mob hit on him. Mafia boss Sam Giancana allegedly canceled the hit after hearing a Sinatra album.