Sylvester Stallone, renowned for his iconic roles in Rocky and Rambo, has reflected on pivotal experiences and profound regrets throughout his life and career, offering valuable insights on transformation, adversity, and the true meaning of success. In a candid discussion, Stallone delved into his encounters with challenges, the evolution of his priorities, and the enduring importance of family, all while emphasizing Stallone life lessons at the heart of his journey.
Early Encounters and Career Shifts with Taylor Sheridan
Stallone’s collaboration with acclaimed writer and director Taylor Sheridan did not arise from the instant fame of hit series like Tulsa King, but from an unexpected meeting decades ago in a Los Angeles barn. Years before Sheridan created successful shows such as Yellowstone and Landman, the pair bonded over their shared struggles and ambitions. Stallone recalled a conversation with Sheridan that set the stage for both their future successes:
“Oddly enough, I met him when I had a couple of old horses. And he would be up at the barn, so I’d be talking to this guy, and it was like talking to a younger me. And we’re talking about writing and I said, ‘why don’t you help me write the last Rambo?’ And he goes, ‘Really?’ And I go, ‘Yeah,’”
– Sylvester Stallone
Stallone further remembered Sheridan’s hesitation and ambition at the time:
“And I barely knew him. And he goes, ‘Write Rambo!?’ And then he says, ‘Well, to tell you the truth, I’m writing a movie called Sicario and I’m going to see if I have it or not’,”
– Sylvester Stallone
For both Sheridan and Stallone, enduring setbacks shaped their creative paths. Stallone noted Sheridan’s struggle finding roles that showcased his talent, paralleling his own early challenges. He recognized the unique value of writers in the industry and how setbacks often precede breakthrough moments.
“And Taylor Sheridan [below in Yellowstone] was also always kind of kept out in the distance, out in the cold. He was never given a part to really show what he had. And then, he complained about it, and he was put out,”
– Sylvester Stallone
Turning Doubt into Motivation and Personal Growth
For Stallone, persistent skepticism about his abilities—especially as he made the leap from film to TV with Tulsa King—became a source of motivation. Through his performance as Dwight Manfredi in the series, he embraced the pressure and proved doubters wrong, sustaining the relentless energy that has defined his decades-long career.
“When they say, ‘he must be at the end of his career’ or ‘he’s a has-been’, I love that, because that wakes me up in the morning. I go ‘yeah! Keep saying that. Keep getting me aggravated’,”
– Sylvester Stallone
Stallone openly acknowledged the uncertainty that comes with reinventing oneself, describing the experience of entering television as a leap into the unknown.
“Everyone was sceptical. ‘Can he do it?’ ‘Why is Stallone doing TV?’ And, in the first year, you are jumping out of an airplane with no parachute, you don’t know what’s going to happen,”
– Sylvester Stallone
According to Stallone, facing challenges is a universal catalyst for resilience:
“And that goes for everybody. When people are challenged, that’s when you wake up,”
– Sylvester Stallone
The Importance of Relationships and Overcoming Loneliness
The actor’s reflections reached a deeper emotional register when he discussed the turbulence in his personal life, particularly his brief separation from his wife Jennifer Flavin in 2022. The subsequent reconciliation underscored, for Stallone, the fundamental human need for connection and love, which ultimately outweighed career pursuits.
“I always considered the worst, most fatal disease in the world is the disease of loneliness. Isolation is so sad,”
– Sylvester Stallone
He recounted the terror of loneliness, of having no one to share life’s moments with. Workaholism once dominated his priorities, but Stallone’s perspective changed with age and hard-earned wisdom. Today, he places his family, especially his three daughters—Sophia, Sistine, and Scarlet—at the center of his life, committing to being present and attentive.
“And I used to be very superficial. I thought work was important. But it’s second,”
– Sylvester Stallone
The professional partnership even extends to family, with his youngest daughter, Scarlet, joining the cast of Tulsa King, which continues to feature actors like Annabella Sciorra, Kevin Pollak, Frank Grillo, James Russo, and Bella Heathcote.
Gratitude, Empathy, and the Responsibility of Privilege
As he surveys his career of more than sixty years, Stallone recognizes the intoxicating nature of fame, and the vital choice between entitlement and gratitude. He stresses empathy and responsibility, noting that most people perform demanding work out of necessity rather than desire. This principle is one he aims to impart to his children:
“So, I have taught my daughters… I say, ‘you are so fortunate, so the only thing I’m begging you to be is sympathetic. Just be empathetic, because 90% of the people are doing things that they have to do. They don’t want to do them, but they have to survive. They have responsibilities, which I think is incredibly noble.’”
– Sylvester Stallone
He draws a clear distinction between material wealth and true contentment. Stallone reflects on how happiness is often unrelated to money, and apathy can be just as destructive as poverty.
“So why did you accumulate all this money, if you’re still a miserable human being? And I find this to be true quite often, when people acquire great wealth. The assumption is that with great wealth comes great happiness. Happiness is free. You can go to some of the slums of the world, and people are smiling; people who have nothing. And then you could go to some kingdom, some mansion, and you just see apathy,”
– Sylvester Stallone
Learning from Pain and the Value of Change
Long-term physical pain from stunt injuries and multiple surgeries marked a turning point for Stallone, reinforcing the urgency of personal transformation. Facing operations that risked paralysis, he realized the necessity of change, not just physically but emotionally and spiritually.
“And that was it. Usually, it takes some transformative moment to wake you up and knocking on death’s door will do it. That’s definitely a wake-up call,”
– Sylvester Stallone
Grappling with these painful wake-up calls led Stallone toward a deeper understanding of what truly matters in life. Looking back, he wishes he had acquired this perspective earlier, determined now to make the most of his remaining years.
“And I think it’s called wisdom of what’s really important. Because, oh my God, I wish I knew 60 years ago what I know now. I’m not exactly young, but I’m going to try to put as much living into life as I can,”
– Sylvester Stallone
Perspectives on Hollywood and Advice for Creatives
Stallone remains actively involved in the entertainment industry, currently working on eight new projects. Despite financial and critical achievements, he cautions against complacency and points to the changing landscape of film and television. He believes that storytelling, not messaging, is the core of compelling entertainment.
“I have seen an industry over 50 years collapse, literally implode on itself. It’s just slowly crumbling. And why is it crumbling? Because we’re not telling identifiable stories. We’re sending too many messages. This is not the post office. We don’t send messages. You try to entertain, you try to enlighten, and the last thing you want to do is go to a movie theater to get a lesson. I don’t.”
– Sylvester Stallone
Legacy, Regrets, and What Truly Matters
With his memoir, The Steps, forthcoming and an estimated personal fortune, Sylvester Stallone stands not just as a legend of Hollywood, but as someone who has faced down adversity, loss, and misguided priorities to distill the central Stallone life lessons. He reminds his audience—fellow actors, writers, and fans alike—that resilience, empathy, and dedicating time to family endure long after the accolades fade. As Stallone continues to hone his craft and pass on his wisdom, he emphasizes that even iconic figures must learn, adapt, and ultimately prioritize what counts most: enduring relationships, gratitude, and finding meaning beyond the spotlight.
