Ring-A-Ding Ding

By Richard Lacayo

You should have been at the Brown Derby last week. Actually, these days it's just the Derby. Hollywood's old watering hole is now a swing club. That's '90s swing--Panama hats and cocktail dresses plus cell phones and plastic. Smoke and libido still hang in the air. So does the spirit of Sinatra. "Obviously," says Tammi Gower, one of the joint's owners, "Sinatra was the epitome of cool." On the night after the great man died, the Derby observed a moment of silence. Then Lavay Smith and Her Red Hot Skillet Lickers bit into My Way.

Sinatra is gone? Sinatrismo lives!

And it has for a while. He survives as the last word in a hipster style all the more fascinating for its plain links to squaredom. The minute that grunge thing came along, circa 1990, you knew it was only a matter of time before Sinatra and the Rat Pack came back into fashion. Uncombed hair and flannel shirts cried out for a counterattack of sharp dressing and flip courtliness with women. Thus "lounge music," cool and dressy, then swing music, hot and dressy, plus a bar scene where lounge lizards aren't dinosaurs anymore. Then the film Swingers, about two guys making their way through the world on terms they borrowed from Frank's life and works. The past year also saw the publication of two histories of the Rat Pack; a pair of Rat Pack movies are in the works (an HBO film starring Ray Liotta as Sinatra and a Martin Scorsese film about Dean Martin); and a few weeks ago, the cable channel TV Land drew its highest ratings to date with a never before broadcast Rat Pack concert from 1965.

Until not so long ago, Sinatra's notion of cool was deader than an imploded casino in Vegas. Bourbon on the rocks and snap-brim hats were your parents'--no, worse, your grandparents'--idea of hip, stuff that looked quaint beside the bug-eyed alienation of the 1960s. Hippies wore blissed-out smiles and ponchos. Sinatra wore cuff links, roughly $30,000 worth in the mid-1950s, when that kind of money bought a house or two. In the Oedipal drama of the counterculture, Frank was the daddy-o who must die. He could swing his raincoat over his shoulder and cock his hat all night. Compared to Jim Morrison, he still looked like the man in the gray flannel suit.

But Sinatra was not to be undone so easily, and not just because anyone with taste in music never let go of him in the first place. His explosive inner life, which he wore on that cuff-linked sleeve, connected him from the first to the big feelings that the '60s passed along to the decades that followed. We just didn't see it at the time. And by now, baby boomers who once turned away from him are old enough to recognize how he created the Rat Pack in part as a defense against his own aging, a way to keep the party going as he reached his mid-40s. What do they have that compares? Seinfeld? It died a few hours before Sinatra did.

A first version of the Rat Pack dates to the mid-'50s, when it convened around Humphrey Bogart. But the name entered the collective consciousness only after Bogart's death in 1957, when Sinatra assumed leadership and gathered in new buddies like Sammy Davis Jr. and Peter Lawford. Their supreme moment arrived in early 1960, when Sinatra, Davis, Lawford, Dean Martin and Joey Bishop gathered in Las Vegas to film the casino-robbery caper Ocean's Eleven. Every night for three weeks, after the day's shooting was over, they all played--and played!--the Sands, a Mob-connected casino in which Sinatra held an interest. They called their act the Summit, a convergence of star power. Crooning, one-upping each other, rolling out booze jokes with their onstage liquor cart, they established their bad-boys-in-black-tie schtick. Sinatra to Martin: "Tell me something, do you fall in the street a lot?" Martin: "It's the only time I get any rest, Frank."

For the new middle class of the postwar years, all this was strangely captivating. The working guy and his wife were discovering prosperity. Sinatra ushered them into cafe society on their own terms: dinner jacket but no top hats. First class all the way but nothing fancy. Ordinary guys were anxious--and anxious is the word--to show that they understood the bits of nightclub chivalry that Frank knew all about, like how to light a lady's cigarette. All the same, they wanted to cut loose, the way Sinatra wore his tie--undone, a sign of his narrow escape from a workaday world that could still seize them by the throat.

It wasn't always a lot of fun to be a woman in that set, where the ladies could be called tramps at a moment's notice. Or to be Sammy Davis Jr., who had to endure Sinatra's cornball racial jesting at its worst. But for Sinatra, the sumptuous early '60s were a Golden Age, when gambling was still glamorous, smoking had charm and "dapper" was something you might actually want to be called. Naturally he was infatuated with J.F.K., just 18 months younger, an Irishman born to the Ivy League credentials and Establishment credibility that Sinatra never had. In return, Kennedy was fascinated by Sinatra's bachelor-in-paradise ways, cultural power and abundant women.

But Kennedy eventually betrayed Sinatra by choosing to stay with the more wholesome Bing Crosby during a visit to California. It was a humiliation that sent Sinatra rightward, into the arms of Nixon, then Reagan, which is where a lot of his audience was going in any case. Years had to pass before he could re-emerge entirely as a lodestar of bipartisan style. "I am," he once said, "a thing of beauty." It was a complicated beauty, but he had a point.

--With reporting by Patrick E. Cole/Los Angeles

With reporting by Patrick E. Cole/Los Angeles