Sylvester Stallone Calls Not Meeting This Film Icon ‘One of the Biggest Regrets of My Life’

Hollywood heavyweight Sylvester Stallone maintains his A-lister status thanks to his impressive list of screen credits. One of the few celebrities to be nominated for both screenwriting and lead actor Academy Awards in the same year for Rocky, Stallone revealed he received a note from an acting legend in 1977 and deeply regrets not making time to meet the superstar in person.

Sylvester Stallone
Sylvester Stallone | Axelle/Bauer-Griffin/FilmMagic

‘Rambo’ star reflected on his youth

Speaking with Esquire in 2021, Stallone looked back on his storied career and admitted that roles came easy to him after skyrocketing to fame with Rocky. The Oscar nominee didn’t have to worry about landing a job at the time, so he wasn’t concerned about his acting abilities.

“In the ’80s I felt like I was going to live forever,” Stallone said. “Because of that, I didn’t pay too much attention. I’d have films lined up for the next two years. They’d call them ‘slots’. The most important thing at the time was just to make sure the slots were filled.”

Now at 75 years old and a plethora of films to his name, Stallone has grown more appreciative of his work in the industry.

“I really didn’t focus on my craft at that age as much as I thought I did,” the Rambo star explained. “I’ve learned that about myself with time. When you get older, you get better. You get some wisdom. You may slow down physically, here and there a little bit, but you add gravitas. … I’m better now than I ever was, if you’re looking closely. I’m more relaxed, and I understand how it works. I don’t squander my opportunities.”

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Charlie Chaplin reached out to Sylvester Stallone

Though Stallone was nominated for two Oscars in 1977 for Rocky, he walked away empty handed. Still, what the Suicide Squad remembered most about the awards that year was a note from a silent film idol.

“There’s a piece of paper on my wall that says something like ‘Dear Mr. Stallone, I want to congratulate you on your Academy Award nominations for Rocky. Signed, Charlie Chaplin’,” Stallone shared. “It was from 1977, and at the time only two other people had been nominated for both Best Screenplay and Best Actor—Orson Welles for Citizen Kane, and Charlie Chaplin for the Great Dictator.”

Stallone revealed that he didn’t make meeting the groundbreaking actor a priority and regrets his inaction to this day.

“I never met Charlie Chaplin,” The Expendables star remarked. “I was really stupid at the time. I was young, thinking, ‘there’s going to be time for that later’. But six months later, he was dead. It’s one of my biggest regrets in life, not grabbing that moment.”

Sylvester Stallone saw similarities between ‘the Tramp’ and ‘Rocky’

Stallone posted about admiration for Chaplin and compared the silent film star’s trademark character to his own iconic role.

“This is one artist I would’ve loved to have met,” Stallone captioned a photo of himself sitting next to a statue of Chaplin in 2021. “I always thought that Charlie Chaplins ‘littleTramp’ always reminded me a little of a Rocky … ( maybe it was the Hat? )”

Stallone agreed with the famous adage from Oscar Wilde on getting wiser with age.

“When you’re between 30 and 40 years old you think you know it all,” he told Esquire. “You don’t know anything. You walk onto a set and there’s a guy 50 years into his career, and that makes you realize how little you really know about what you’re doing.”

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