Fifty years in entertainment is a long time. Long enough for Bennett to wise up ten times over, to tackle his excesses and stare down his fears. But mostly long enough to not change at all

It's only once you're seated on one of the off-white couches in the vast living room of Tony Bennett's Manhattan apartment that you start to wonder if you might not be in real trouble.

There's nothing new to write about this man. God, you're screwed.

Sure, he's publishing his autobiography, The Good Life, this fall and releasing a children's album at the same time called The Playground. But his larger-than-life stature, which dwarfs both the room and the unparalleled view of Central Park, reminds you that he's one of the most written-about figures in American music history. What do you write about the man who outlived Sinatra?

You're supposed to be a member of the generation responsible for Bennett's '90s comeback, which has been documented more than anything else in his life. Bennett blipped back onto pop culture's radar (though he insists that he "never went anywhere") thanks to the spot-on machinations of his manager son Danny. He guested on The Simpsons, showed up in a top hat and shorts at the 1993 MTV Music Awards to jam with the Chili Peppers — and then there was 1995's defining Unplugged set, where he paired up with k.d. lang and Elvis Costello. Seemingly overnight, he'd gone from obscurity to heavy rotation on MTV and all of a sudden, Tony Bennett was cool. Not the kind of kitsch or campy cool that's slathered in irony, but inherently, authentically, been-around-through-a-million-fads-and-never-changed-a-hair cool. And that's precisely what was missing in the music industry when Tony Bennett walked back in.

It was, as with everything in Bennett's life, a question of timing. In the late '80s/early '90s, artists who had once been emblems of coolness were so busy reinventing themselves (and being reinvented by nearsighted label execs) they forgot to ask anyone who ever bought one of their records if they really wanted change. Change to compete with what? Disposable pop? And so pop's foundations — artists on whom you could count for constant reassurance when everything else on the dial was drivel — bottomed out. I'm talking about the Rolling Stones, Tina Turner, Paul McCartney, Billy Joel, Paul Simon et al., people whose authenticity was once unquestioned and whose place at both the center and the cutting edge of music seemed perfectly natural. All of a sudden, you turned around and Mick Jagger, who'd once swaggered directly into our collective hearts was doing the "Harlem Shuffle."

At the same time, the dubiously-named MTV Generation had been weaned on music characterized (as fun as it was) by total disposability, and this, especially as a marketing gimmick, was getting old. In this kind of void, Bennett barely needed to sing a note — a note of some chestnut he'd sung countless times for generations of fans — to crystallize a collective craving for something real. So he donned a natty gray suit and tie, leaving his heart in San Francisco all over again — and everyone else in the dust. As one writer put it, "Bennett didn't make a comeback. We did."

***

So this is what Tony Bennett and I are talking about. We're talking about how last year, all of a sudden, everyone sort of realized that Paul Simon and the boys were well into the August of their years. Amidst newfound savvy about What the Public Wants, amidst career-spanning box sets, reunion tours and TV tell-alls, somebody dared ask The Question, one that was picked up and echoed in every medium in existence: Will they ever be as great as they once were? And can box sets and VH1 specials really sustain them through another 20 years' worth of career?

This is what I'm discussing with a 72-year-old man who has more projects on more burners than most of these once-icons combined, whose recent album sales have eclipsed those at the height of his '60s fame and who's about to hit the road in Europe on the bill of an alt-rock festival. More than half a century in the music business has provided him with enough experience to know better, and he's one of the few who've paid attention. He has his own Zen, if you will, and when I ask him if he might let music's lost lambs in on his secret, his eyes twinkle as he tries to recall an old Oscar Wilde saying. "It's like being a lamp post telling a dog what to do," he responds. Cryptic? Maybe, but nobody ever asked Confucius to elaborate. Besides, what comes next is more straightforward: the master unrolls his blueprint for longevity. Take note.

1. Don't change with the times.
When the Britpop of the late '60s edged Bennett off the charts, he turned to Count Basie for advice. " 'Don't change an apple,' that's what he said to me. 'Keep doing what you're doing, and don't worry about it.' He was right."

But as his sales dipped, his managers at Columbia Records didn't see it that way. His 80-album relationship with the label came to an abrupt end when, in 1971, they wanted him to sing rock 'n' roll and he refused. "They wanted me to record stuff I would've been ashamed of for the rest of my life. I couldn't do it." He's now back on the label, no hard feelings. "They tried the same stuff with Duke Ellington, you know. You can't take it personally."

2. Don't imitate.
"If you're influenced by one person, it's thievery, but if you're influenced by everybody — Louis Armstrong, Sinatra, Pavarotti, whoever — then that's research," says Bennett with a benevolent smile.

Specifically, we're talking about Harry Connick, Jr. "I met him when he was about 15, and he had a lot on the ball. I think he's going to be around a long time. But he imitates Sinatra too much and that's bad, because then you're just one in a chorus of imitators. He has a natural voice. Eventually he'll realize that, and he'll just be himself. But that's the hardest part." The singer's raspy speaking voice drops to a whisper. "If you don't get in line and become one of the cattle — if you try to avoid the ring in the nose — you're out. If you do what they want everybody to do, then you're in." He shrugs. "But you're in a big crowd."

Does he think honesty is fashionable in music right now?

"I think it had better be, because the music won't last if it isn't."

3. Sow your wild oats. Completely.
Tony Bennett, wild child? "Absolutely. I only grew up in my '40s," says Bennett, who admits he tried everything he could get his hands on and "wouldn't be around today" if he hadn't wised up. Both his marriages fizzled as a result of his wilder side and constant touring. "I thought life was about wine and women. I never went to sleep." The final straw? "Perry Como had a lot to do with it. I'm Italian, he's Italian; he took one look at me and said, 'You're coming with me.' He walked me over to a church on Ninth Avenue and right into a confessional box. It got me thinking about myself for the first time."

4. Be eclectic.
You don't know eclectic until you've seen Tony Bennett's CD collection. The singer listens to everything, from Sting to French punk to Chinese folk music. "I'm just trying to understand it," he says about the latter, and that's the best part about Bennett, his willingness to take other music, younger music — music, period — on its own terms. His openness to new things is a gift, one that comes right back at him from his under-30 fans. Take Madonna, who counts Bennett among her favorite singers. "I love her. She's a great artist and people misunderstand her like they misunderstood Marilyn Monroe. Every time I see her, she's doing something very, very creative. Only people don't see that part — they can't get past her boobs. And she's saying that's all right. Only people can't get over that it's all right."

5. Perform for everybody.
"I don't like categories and demographics. Why can't I be on MTV?" Bennett recalls asking his son/manager Danny in the 1980s. Despite the best efforts of legions of marketing executives, Bennett's never believed in splintering his appeal to fill various niches. And the public has so far proven him right: As a New York Times critic wrote, Bennett "has not just bridged the generation gap, he has demolished it."

His latest project, a children's album, may seem like the exception to a 50-year rule, but then again, Bennett's just doing what he's always done, only instead of duetting with Sinatra, he's doing harmonies with Kermit. "It's a complete departure from everything I've done," he admits. "When the idea first hit me, I didn't quite know what to do about it." Bennett consulted everyone from Mister Rogers to Rosie O'Donnell for advice — O'Donnell loved the idea so much, she wound up on the album. "I've sung for kings and queens and presidents," Bennett says. "They were all children once."

6. Don't believe reviews, especially if they're glowing.
"The press has been very good to me," says Bennett. "You get the occasional critic who has indigestion when he walks in, or who's held a grudge his entire life because he tried to play the clarinet when he was 12 and couldn't do it, so he's become a critic of everyone else. Even if you get the most glorious review that makes you feel like a million dollars, it's still not accurate, because critics never get it. The public gets it. They've worked hard all week long, they just want to be entertained. If someone's going to get dressed up and hire a babysitter and spend money to come to see you, these are the people who matter. The public is the only critic you need."

7. Listen to the kids.
One segment of this public Bennett pays particular attention to is the under-30 crowd. "They're tremendously intelligent, and terribly misinterpreted. I hate the way marketers pigeonhole them into categories like 'slackers' or 'Generation X' — what does 'X' mean? It's a bigoted characterization. Marketers just don't know what to do with them. Here's this generation of people, and they know what they want. Take the swing craze. The swing clubs have been packed with young people for years, and the marketers are only picking up on it now. The kids should be telling us what to do."

But Bennett turns less than mellow when talking about what those same kids have to go through to kickstart a music career these days. "I can't get over the talent, the amount of talent in the world. I meet these people, I'm in awe of them. But they're treated too cruelly. The labels will give them a contract and if the record doesn't work within five weeks or something, they're dead. When I started on Columbia in the '50s, they gave me a whole year to get used to it, and they trusted me. Now they say, 'Next.' "

8. Have causes, but don't use them as outlets for publicity.
Well before celebrity causes became fashionable, Bennett marched for civil rights in Selma and refused to perform in South Africa because of apartheid, and that's just the tip of the good-deeds iceberg for the man whose countless (but low-profile) charity gigs have earned him the nickname Tony Benefit. But the only cause he'll discuss with me is gun control. "The lowest form of human behavior is violence, and guns create violence. You make a gun, it lasts 500 years, so once you sell it, it's out there forever. I admire Barbra Streisand for speaking out against the laws," he continues, referring to the recent high-profile spat between Streisand and the National Rifle Association. "It's a very human thing to do, and for her to be condemned for speaking against that is just idiotic."


9. Have a sideline — and keep it on the side.
These days, several thousand discretionary dollars might put you in the art market for a Benedetto — a small one. Not bad for the boy who dropped out of New York City's High School of Industrial Art as a teen, devoting himself to singing full-time so he could help his seamstress mother financially. Now, Bennett paints — mostly in oils — everywhere: In Central Park, on balconies of every hotel he stays in, in every kind of weather imaginable. A book of his paintings and reflections on art, What My Heart Has Seen, has become a bestseller.

He signs his works "Benedetto" to "separate the two careers. When I paint, I use my real name. When I sing, it's Tony Bennett, thanks to Bob Hope. He heard me sing down in the Village and he wanted to take me on the road with him. I told him my name was Anthony Dominick Benedetto. 'Too long for the marquee,' he said. 'Let's Americanize; we'll call you Tony Bennett.' He had no idea there would ever be a singer called Engelbert Humperdinck." As if that wasn't enough of a sideline, Bennett is filming a documentary on art. And I do mean filming: He's doing all the camera work himself.

10. Don't let age weigh you down.
Their very age insures that rock's elders have lived through the kinds of slings and arrows reserved only for the rich and very famous. Some emerge enlightened and mellowed, some bitter, still others simply at a loss for inspiration, and all of these states bleed through to their music. In Bennett's case, there's a melancholy quality to his voice — one his earlier recordings only hint at — that's come into its own without ever losing its sense of hope.

When Sinatra, whose younger voice was full of swagger, sang "It's Not Easy Being Green" towards the end of his career, a sorrowful sweetness crept into his delivery. But Bennett's always played soft shoe to his bittersweet soul, singing about love's woes with a smile on his face and not an ounce of resentment in sight.

"The philosophy of some of these rock 'n' rollers in the '60s was, I'm going to make a lot of money and then I'm going to retire. Retire? To what? If you're an artist — if it's not a choice, but it's what love and what you have to do — you'll be doing it until the day you die. And you'll get better at it."

Bennett points out that Mick Jagger used to say he wouldn't be performing when he was 50, " 'like Bennett or Sinatra.' Well, he's still doing it," says the singer with a chuckle and almost grandfatherly indulgence.

11. Have a voice.
When Tony Bennett says "unplugged," he means it, and I'm not talking about his now-legendary MTV stint. I mean unplugged as in, shutting off the mike and pitching a tune — unstrained — to a packed house without losing a note, which he's done from Carnegie Hall to the Vatican, and everywhere in-between. His secret? "I drink a lot of water, and I get a lot of sleep." Still, if all it took were some Evian and a Sealy Posturepedic, most singers wouldn't need the magic of filters, amps and reverb.

12. Stay in shape.
72 years old. 200 sit-ups a day. Any questions?

13. Never let any of it go to your head.
Bennett is a human anecdote machine, and the pearls he slings my way in a single hour could keep a decade's worth of dinner parties afloat. So it's without the usual exaggeration that the press release for his autobiography The Good Life trumpets the book as "an oral history of five decades of the American music and entertainment scene." Exhibit A: He met Billie Holiday once, in the '50s, at a club in Philadelphia. He was starting out, she was smoking. "She took some bills from her stocking and said 'Get me a gin.' Gosh," Bennett pauses, giddy at the recollection. It's not that he's being pretentious, it's just that he was there, in utter awe at being in the same room as Duke Ellington, Ella Fitzgerald, Holiday.

Tony Bennett is, if nothing else, incredulous about where life has taken him, from his grandparents barely making it out of Italy when Mount Vesuvius erupted to becoming the one singer Sinatra told people to keep an eye on, to playing sold-out shows to pierced audiences. "Here I am, an Italian, singing Jewish music from Broadway and black music by jazz artists. Only in America!" he says, running a hand through his white hair. "I once asked Frank why we lasted the way we did, and he said, 'Because we sing good songs.' All I'm doing now is what I've always done. And today's young people are definitely the most enthusiastic audience I've ever had. It's unbelievable," he finishes, shaking his head.

There's something touching about the singer's need to remind you, as he's mentioned in a thousand interviews, that in his "day," he had as many hits as Michael Jackson. Where's Jacko tonight, as Bennett plays to another sold-out house, one of his 200-odd gigs a year? You want to tell him that he doesn't need to keep reminding us that he used to be in — his is in. But the refusal to let this acceptance latch on to his ego is part of Bennett's appeal. "I need more than one lifetime to do everything I want to do. I'm not going to be able to do it, but I'm going to go for it."

In a show at London's Royal Albert Hall, Bennett eases his way through "The Best is Yet to Come," and the crowd, old and young, goes wild. After the last note, an elderly fan in the second row cuts through the applause. "Tony! Tony!" she screams in a thick Cockney lilt. Bennett stops, turns. "What is it, darling?" "I Wanna Be Around!" she shrieks, requesting his 1956 hit, a signature number to this day. The twinkle in Bennett's eye reaches all the way out to the twenty-first row. "So do I, sweetheart," he says. "So do I."

(music choice magazine)