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“The problem isn’t sitting down,” Sylvester Stallone announces as he slowly lowers himself into a treacherous-looking camping chair on the lawn of a waterfront estate in the Hamptons. “It’s getting up.”
It was a few weeks past his 79th birthday in July, and Stallone had left the East Hampton, New York, summer house he recently purchased for a reported $25 million (he resides mainly in Palm Beach, Florida) and come to a neutral spot nearby to talk about his life and career, including his Paramount+ series Tulsa King (in which he plays a fish-out-of-water crime boss) and his work on a forthcoming memoir.
Stallone has been one of Hollywood’s biggest earners, to use Tulsa King’s gangster lingo, for almost 50 years. He has been the star, and sometimes writer and director, of three film franchises that together have grossed more than $3 billion worldwide: Rocky (and its Creed spin-offs), Rambo and The Expendables. More remarkably, he has sustained that success across decades: Rocky launched his career in 1976 via the story of a hapless, turtle-loving Philadelphia boxer who’s given one shot at the heavyweight title; his biggest-grossing movie, The Expendables 2, opened in 2012; and Tulsa King first streamed in 2022. (Its third season started in September.)
Today Stallone is still physically imposing, with a narrow waist that flares into that battleship chest and shoulders. He’s somewhat reserved and stylish (in jeans and a Tom Ford dress shirt) without being flashy. Even when he’s talking about his insecurities and disappointments, he exudes confidence and an unflappable affability.
Rocky Balboa is such a famous and enduring character in the American consciousness—an archetype of an uncultured palooka—that anyone grunting, “Hey, how ya doin’?” in a slurred, working-class accent instantly conjures the character—and the actor. So I ask Sly if people are surprised when they meet him.
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“All the time. Quite often, they’re stunned. They think I am Rocky,” he says, chuckling, though it clearly grates. “They think, He’s dumb, and it’s hard for them to come off that.”
Depending on how much you know about Stallone, lots of things about him might surprise you. For starters, in stark contrast to the Rocky and Rambo personas he is so often confused with, he’s well-read—“Do you remember Kafka’s Metamorphosis?” he asks later in the context of discussing Tulsa King—as well as a painter and art collector who has owned works by Claude Monet, Francis Bacon and Pablo Picasso. He wrote all six Rocky movies and directed four of them, cowrote five Rambo films and cowrote three Expendables, directing one.
Less well remembered is that he has had a roller-coaster career, bombing in some roles and movies and even wandering the Hollywood wilderness for nearly a decade in the late ’90s and early 2000s, unable to get work. Yet he has always found a way to get back into the ring and, often, revive his career in box-office triumph. Indeed, in December he will be among those feted at the Kennedy Center Honors for his culturally important body of work.
“I was surprised by what a great orator he is,” says Emmy-winning actor Dana Delany, 69, who plays rancher Margaret Devereaux, the love interest of Stallone’s character, Dwight Manfredi, on Tulsa King. “Since Rocky, he’s understood the balance that makes a film star: a little danger, a little inaccessibility, but ultimately likable. You end up rooting for him. To me, he’s one of the last of the stars. There aren’t many people like him anymore.”
I’ve interviewed Stallone before—during those rough, in-the-wilderness days—and what surprises me this time is how little he seems to have changed. Funny, sure of himself but not cocky—I’d almost call him winsome. Late in the afternoon, near the twilight hour, he lights a cigar, settles into his seat facing me and the becalmed Sag Harbor, and opens up about his singular journey to stardom and beyond.
‘I Didn’t Have a Childhood’
When Stallone was born, at a charity ward in the blue-collar Hell’s Kitchen section of Manhattan, a forceps accident caused permanent nerve damage on the left side of his face. As a result, he has always spoken slowly, with a slight lisp, in a preternaturally low voice and with a kind of permanent snarl. Stallone’s father, Frank, a hairdresser, and mother, Jackie, an aspiring entertainer who worked as a cigarette girl in a nightclub, both had violent tempers, and Sly and younger brother Frank Jr., who became a singer, were beaten regularly, sometimes with a riding crop. (Sly was taught how to ride and play polo by his father.) Stallone later found out that when his parents married, his mother was already wed to a man with whom she had a child. All told, she had four children with three men, though she denied it when Sly asked her about them. To hear him tell it, she was his first and most damaging critic.
SS: My mother didn’t want me. She said, “If you had any defect whatsoever, I would have put you on the windowsill and let you get pneumonia. And I’d be doing you a favor.” And she thought that this was OK to tell me that. She was a narcissist with a borderline personality disorder. Also kind of witty, but in a wicked way, at other people’s expense. And she hated affection. She couldn’t give it. She never hugged me, my brother—forget a kiss. My father certainly was not prepared to be a father. They really didn’t want children, and they had them and thought, So how do we get rid of them?
I was extremely hyperactive. So they sent me at age 2 to a boardinghouse in Jackson Heights [in Queens, New York]. Transients, salespeople, just in and out. I lived there for almost four years. I never went home, and my parents came maybe once a month for an hour. I didn’t have a childhood. It was just taken away. I was around adults all the time. So I started to talk to adults.
And I think it paid off further down the line when I got into writing stories. But I never bought that Nietzsche quote—“That which does not kill you makes you stronger.” No, that which does not kill you leaves you pretty f---ing beaten up, and you’re never quite the same. It made me more defiant, and, yeah, I might have learned something, but I left a piece of myself there—as we leave pieces of ourselves throughout our life when we have these different traumas—rough childhoods, death, divorce.
‘I Was Always Trying to Attract Chaos’
Sylvester (Michael) Stallone in eighth grade in 1960. He attended Montgomery Hills Junior High School in Silver Spring, Md.
Seth Poppel/Yearbook Library
Stallone passed through about a dozen schools, compiling a record of fighting and failing courses, including finally Devereux, a Philadelphia-area school for emotionally troubled kids. He has joked that some classmates voted him Most Likely to End Up in the Electric Chair.
SS: I was so disruptive. Once, they put me into a day camp, and when everyone went out for a hike, I went into the cabins and took all their pocket knives—25 of them! And they knew it. They’d say, “You took our knives! Thief, thief, thief!” And they kicked my teeth in. But I was trying to attract chaos because I couldn’t function if everything was copacetic.
I finally channeled it when they put me in Devereux. That’s where the state would send the incorrigibles. We were not dangerous; we just didn’t fit in. It was 12 months a year. That’s when I really started to focus on art. I became quite proficient at it. They tell everyone to draw a horse, and you’d see: horse, horse, horse. “OK, that’s very good, Marvin. A horse.” And then they’d look at mine, and it was this contorted thing. They’d go, “That doesn’t look like a horse.” And I said, “That’s what the horse is thinking.” So I found a way to paint abstracts. That’s how I started to interpret and started to channel. I stayed there for two years and then eventually found an ad in the back of Popular Mechanics for the American College of Switzerland. It was 89 students who were basically dysfunctional losers sent over there by their parents, like, “Get out.” I got in because they needed a phys ed instructor, and I lied on the application: I said I was a champion Golden Gloves boxer and this and that. But I wasn’t even athletic!
I got into acting by accident, just joined the drama club. I wasn’t planning to be an actor. I love when people go, “Oh, I knew what I wanted to do at age 4.” Stop it.
‘Acting Is 97 Percent Guaranteed Unemployment’
A stage was the first place Stallone felt comfortable. “I wasn’t nervous,” he says in the recent Netflix documentary Sly. “I felt in control of the situation, because this comes easily to me.” He took his poor grades to the University of Miami, where he continued to study acting. After dropping out, he went to New York with nothing but lint in his pocket and slept where he could, often at the Port Authority Bus Terminal. Casting agents snubbed him, he says, because his birth injury made him ill-suited to play anything but goons and thugs; pre-Rocky, he was cast in mugging scenes with both Woody Allen and Jack Lemmon, in separate movies. Bigger roles came in The Lords of Flatbush—where he met and became lifelong pals with Henry Winkler—and Death Race 2000, but true success as an actor eluded him.
SS: I had tried to pursue something that made me happy. But acting is 97 percent guaranteed unemployment. I might have had a career for 15 years as the second goon at the door: “Hey, boss, let me open the door.” I realized I was never going to make it as an actor. That’s when I decided to learn about writing. I was terrible. I mean, I still, today, don’t know what a pronoun is. I’m just still working on a verb. It’s an action word, right? Because it doesn’t matter in screenwriting. When you’re writing dialogue, the way you speak is as personal as your fingerprints. I just had that ear. So my point is, I knew I was going to be a thug, and then an older thug, and then an unemployable thug. But maybe, instead, I could write a story about a thug who is not a thug. He’s really quite a broken man, kind, and just realizes he’s a failure.
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‘That One Comment Changed My Whole Life’
Stallone took a $35-a-week job as an usher in a midtown theater so he could watch movies over and over and study why they did or didn’t work.
In 1975, Muhammad Ali defended his championship against Chuck Wepner, a New Jersey boxer whose day job was selling liquor. The fight wasn’t supposed to last long, but Wepner, a 40-1 underdog, knocked Ali down—becoming one of only four fighters ever to do so—and lasted until seconds before the end of the 15th round, when Ali won on a TKO.
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