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Fascinating Stories About Sylvester Stallone, Hollywood's Most Macho Star

Updated January 10, 2020 140.4k views14 items

Sylvester Stallone. He's Rocky, he's Rambo, he's one of The Expendables, and he's without a doubt one of the best known actors on the planet. Many stories about Stallone coincide with the manly persona you've seen on screen, but they also reveal the true complexities of the man himself. 

Decades into his career, Stallone is still making movies. The actor, director, writer, and producer has taken on the role of entrepreneur and advocate, blending his personal and professional interests along the way. Stories about Sly give you some insight into how unbelievably macho he can be but also offer a small little glimpse into some of his insecurities, too.

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  • He Encouraged Dolph Lundgren To Knock Him Out In 'Rocky IV'

    While doing press for Rambo V: Last Blood in Cannes, France, in May 2019, Stallone recalled his first interactions with Dolph Lundgren. As the antagonist in Rocky IV, audiences weren't supposed to like Ivan Drago and, from Stallone's recount, he didn't like Lundgren either.

    This was by design. When Stallone first saw him, he thought Lundgren, "was like the real Terminator, and I go, ‘I hate this friggin’ guy.' He’s just too perfect, too good looking. And if I loathe him, I’m sure the world will. He’s not really, but he looks like something that’s a thousand years in the future. This is not a guy you see waiting on your table."

    Stallone knew Lundgren was perfect to play Drago, the ideal "superhuman being... someone who would be overwhelming... someone who is literally perfect. Indestructible. Shoulders, calves, forearms, giant butt, neck, back, everything." One day, while shooting, Lundgren hit Stallone, "so hard he almost stopped my heart." As a result, Stallone challenged his co-star:

    I told him, "Why don’t we just do it? Just try to knock me out. Really cut loose as hard as you can." That was a really stupid thing to say. Next thing I know, I’m on a low-altitude plane to the emergency room, and I’m in intensive care for four days.

  • He Was Voted 'Most Likely End Up In The Electric Chair'

    In the midst of his parents' troubled marriage, Sylvester Stallone spent his first five years living in foster homes in Hell's Kitchen. As a young boy, Stallone's distinct facial features resulted in bullying, prompting him to get into numerous fights. He was suspended often and had poor grades, eventually getting kicked out of several schools.

    A testament to his bad behavior, Stallone once said, "When I was in junior high school, the teachers voted me the student most likely to end up in the electric chair."

    After his parents divorced, Stallone moved to Philadelphia to live with his mother. There, he went to a school for troubled youth. Later, as a "straight-D student," his mother sent him to a private college in Switzerland. He studied drama before transferring to the University of Miami, where he focused on the dramatic arts and began writing.

  • He Took A Role In An Adult Film Out Of Desperation

    Stallone studied the dramatic arts at the University of Miami but never graduated, opting instead to return to New York to become an actor.

    Stallone continued to write, but he soon took a role in a softcore film called The Party at Kitty and Stud's - something he took because he was sleeping in the bus terminal at the New York City Port Authority. Stallone explained, "It was either do that movie or rob someone, because I was at the end - the very end - of my rope." 

    Stallone took small roles when he could get them but supplemented his income with odd jobs, including cleaning lions' cages at the Central Park Zoo. He was also fired from a movie usher position after he was caught scalping tickets.

    According to Stallone's site, he'd participated in thousands of casting calls by 1973. In 1974, Stallone got a role in The Lords of Flatbush, a job that earned him his first writing credit for providing some of the film's dialogue. 

  • He Once Tried To Break Up With A Longtime Girlfriend Via Fed Ex

    Sylvester Stallone has been married three times - first to Sasha Czack, then to Brigitte Nielsen, and, finally, to former model Jennifer Flavin. His relationship with Flavin began in 1989, but they took a break from each other in 1994. To end the relationship, Stallone sent a letter by Fed Ex to Flavin's home. According to Flavin, "He sent me a six-page handwritten letter," which she also called "pretty sloppy."

    Stallone was cheating on Flavin with fellow model, Janice Dickinson, something that shocked Flavin. She said, "It hit me like a ton of bricks...I had no idea this was going to happen. We talked about us having children, about when I was going to get pregnant. We were already picking names, marking down names that he liked and I liked.”

    The two reconciled a year later and wed in 1997. They remain together, with Stallone telling an interviewer in 2010, "I’ve never had more fun. I learnt that from my wife… It took me 19 years to realize she’s always right. I realized that women have a knack, at least Jennifer, for making incredibly erudite, wise, smart decisions."