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On the Sly

Sylvester Stallone—just as much an action hero today as he was in his Rocky youth—reveals how he’s still fighting for (and winning) America’s heart

Tell someone that you’ve just met Sylvester Stallone, and the first question is always the same: How’d he look? The thinking isn’t malicious. It’s just that Stallone helped define masculinity for a generation of men, perhaps more so than any actor since Steve McQueen. He understands that we are complicated, that we are all two sides of the same coin: Rocky, the sensitive, wounded warrior in search of love and approval, and Rambo, his polar opposite—a veined-out, one-man army and hero of the Reagan years. 

We’re scheduled to meet at the Peninsula Hotel, which makes perfect sense. Stallone is timeless. And this place is, too; it’s all pastel colors, floral prints and oversize bread baskets. Stallone enters the dining room right on time, dressed in a black, military-style dress shirt that strains to cover his still-hulking frame. He walks with the slow gait of a returning champion as he takes in the room. You actually have to stop yourself from shouting, “Yo, Rock!” as he wraps his massive hand—like a giant slab of concrete—around yours.


So, how does he look? Fucking fantastic. Like a Picasso painting, with a nose slightly off-center and big, sympathetic eyes. His wrist is so thick, his oversize IWC watch still somehow looks like a toy. His hair is salt-and-pepper—more natural than the oil-slick he sports in The Expendables, a surprise hit franchise about aging mercenaries that has earned some $580 million dollars at the box office worldwide. (A third installment is due out this summer.) Stallone broke his neck filming the original in 2009 after he was accidentally thrown into a pile of bricks. The injury required something like seven surgeries to heal. This is 67.

Yes, 67. If you’re surprised he’s still kicking ass at the age some men start wearing diapers, you haven’t been paying attention. When hasn’t this guy been underestimated? Stallone, a man you probably thought was illiterate, earned Academy Award nominations for best original screenplay and best actor in the same year, for Rocky. He’s only the third man in history to have done so. (Charlie Chaplin and Orson Welles were the other two. How do you like them icons?) Rocky may be a fictional character but he’s still the Patron Saint of Philadelphia. The steps he climbed in front of the Philadelphia Museum of Art—known to all as the Rocky Steps—are hallowed ground. There may be other iconic stars from the ’80s, but there’s no public landmark named after the Terminator.

Without question, Stallone’s at an unlikely, yet fascinating, point in his career. He’s at that age where his films, like Judge Dredd and Death Race 2000, are being remade. Rocky, meanwhile, is now a Tony-nominated Broadway musical (Stallone came up with the idea with longtime producing partner Kevin King Templeton). Yet he hasn’t changed with the times so much as bent time to his will. Last year’s Grudge Match, about aging boxers, proved he could laugh at himself, but you’ll notice he left the Viagra jokes to Alan Arkin. That’s ’cause Stallone’s still got it. The Expendables may be the Geriatric Avengers, but dude’s very much on the frontlines.

The cast of The Expendables

The cast of The Expendables

For all his success, there’s pain there, too, lurking beneath his taut, tattooed chest. For a window into his soul, look no further than his paintings. Yes, Stallone is an artist, exhibiting his work last year in a solo show at the Russian Museum in St. Petersburg. One piece, entitled Champion Due, shows a weathered, tired boxer in the center of a ring with blood-red tears streaming down his cheeks. Stallone wears his heart on his sleeve, then wipes it all over the canvas.

“A little Campari today?” the waiter asks as we sit down. Apparently Stallone’s a regular at the Peninsula. He even lived at the hotel for two years in the late ’90s while he was searching for the right house.

“Bring me a little iced coffee,” Stallone says, perusing the menu. “I’m gonna have something light,” he adds. Perhaps. But the conversation is anything but.

Sylvester Stallone has been famous for so long you’ve forgotten parts of his story. The Rocky years were followed by the Planet Hollywood years and then the Exile, when the work dried up. Stallone leans in, happy to reminisce, telling me about the time he met John Wayne at the People’s Choice Awards in 1977. In as sure a sign as any of how different awards season is these days, Stallone tells me he dressed himself for the event. In a tuxedo he rented.

“I was in this stupid tux and ruffled shirt,” he says, ordering a bowl of chicken soup. “Here is the guy, coming across to me. Let me introduce myself. My name is John Wayne. Welcome to Hollywood.” The moment was so seminal, Stallone still has a photo of it on his iPhone, in a folder marked “Celebrities.” This digital detail speaks volumes: Despite all his success, this guy still thinks of himself as an outsider. Years later, at the opening of a Planet Hollywood in the south of France, Stallone took a page out of Wayne’s book. “This story is not meant to embarrass anybody,” he tells me. “But I said, You know what, there’s Johnny Depp and Leonardo. They’re just hanging out. I walked across the room: ‘Hi guys, welcome to the business. You’re doing a great job.’ ” The young, would-be stars forced a smile and returned to their conversation. “They went, ‘OK,’ ”  Stallone says, with a laugh. “They were shy. I’m sure they appreciated it.”

Stallone’s voice is like an old gravel road; rough and winding, and who knows where it will take you. His stories are dispatches from another time (a better time?) in history. As if on cue, Larry Flynt—the 71-year-old political provocateur and founder of Hustler magazine—passes us. Stallone flags him down. “Larry, hi. It’s Sly!”

“Hello brother,” Flynt says. “Behaving yourself?”

“Are you crazy?” Stallone says. “Life’s too short for that, my friend.”

NEXT: “People were appalled. I mean, appalled.”

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