The Toughest Guy Around
While the hero archetype has always been around in film, the 1980s introduced a whole new class of Hollywood macho men, one of the most iconic of which was Sylvester Stallone. Whether he played a boxer, a veteran, or a law enforcement officer, Stallone was integral to ushering in the era of classic action stars. However, behind the scenes, he may have personified the worst parts of this masculine stereotype.
1. They Had Different Careers
Born on July 6, 1946, Sylvester Stallone would go on to embody several different roles, even outside that of an action star, but his parents were the ones who truly led diverse lives. His father, Francesco Stallone Sr, spent his time playing polo when he wasn’t working as a hairdresser. On the other hand, his mother, Jacqueline Stallone, worked two jobs as a promoter for women’s wrestling and a celebrity astrologer.
Unfortunately, he experienced hardships from the very beginning.
2. They Made A Mistake
Although Stallone was young when his parents ended their seriously unhealthy marriage, his problems began even before then. On the day of his birth, the doctors had to use forceps to deliver him, accidentally severing a facial nerve in the process. This gave him a lifelong speech impediment and partial paralysis on the left side of his face.
Because of this, growing up came with its own struggles.
3. They Picked On Him
While it may be hard to believe, seeing as he became the pinnacle of the classic tough guy, Sylvester Stallone still experienced the malice of his classmates as he grew up. His facial paralysis and slurred speech earned him no small amount of teasing, and he even had to leave his childhood nickname of “Binky” behind, as the other kids changed it to “Stinky”.
The effects were long lasting. Even after high school, he wasn’t totally committed to education.
Sylvester_Stallone.jpg: Towpilot
derivative work: Oxilium (talk), Wikimedia Commons
4. He Dropped Out
Although Stallone’s troubles in his early years resulted in multiple schools expelling him, he worked hard at his studies and continued to college after his high school years. However, following his stints at several institutes over the next few years—including one in Switzerland—he decided that academia wasn’t for him and quit in 1969.
During this time, though, he got an intriguing taste of what could be...
5. He Had A Different Name
Despite formal education never agreeing with him, Sylvester Stallone left school and moved to New York specifically because he had caught the acting bug. Having studied drama at the University of Miami, he pursued his dream in 1969, booking a stage role under the name “Mike Stallone” since—according to several biographies—Michael was his birth name.
Still, success didn’t come to him right away.
6. He Was Desperate
Stallone was still far off from his true breakout role, but technically speaking, his first time starring in a project was in 1970, with the inappropriate film The Party at Kitty and Stud's. This wasn’t the kind of acting he had moved to New York to do, but he later explained that he had no other choice, as his landlord had evicted him, and it was the only job he could find.
Fortunately for him, he wouldn’t have to live on the streets for much longer.
Epoch, The Party at Kitty and Stud's (1970)
7. They Moved In Together
Stallone's initial years in New York may have been some of the hardest to endure, but he at least found someone to brighten up his life. He began a relationship with Sasha Czack, who was also trying to break into the acting world. She allowed him to move in with her and worked as a waitress to provide for them both.
Even so, his pursuit didn’t get any less difficult.
8. He Nearly Gave Up
As the 1970s continued, Sylvester Stallone still chugged away, but was growing more disheartened by the day. Applying to be an extra in the upcoming film The Godfather, he was quickly rejected, and instead found work in the comedy What's Up, Doc?. However, his role was barely noticeable, and he probably seriously considered abandoning his dream.
But just in time, his endless persistence paid off.
9. He Got A Gig
Although Stallone found work in 1973 as the main character in the film The Lords of Flatbush, financial issues stretched the production over the next couple of years. In the meantime, he was pleased to acquire his first real starring role in an independent film titled No Place to Hide—later renamed Rebel.
At the same time, things in his personal life were looking up in a major way.
Columbia, The Lords of Flatbush (1974)
10. They Joined Together
Through all his acting struggles and doubts, Sasha Czack had stood by Sylvester Stallone, supporting him both emotionally and financially. It only made sense to take the next step, so on December 28, 1974, the two married. Before the end of the decade, they would have two sons, Sage and Seargeoh.
Meanwhile, Stallone had had enough and took his career into his own hands.
11. He Made His Own Story
In the year after his marriage, Sylvester Stallone was lucky enough to find more work, but he realized that if he was to play the exact character he wanted, he would have to create it himself. Fortunately, while at a boxing match between Chuck Wepner and Muhammad Ali, he had a burst of inspiration. Three days later, he had produced the first draft for a new film titled Rocky.
However, this character wasn’t for just anyone to inhabit.
Anastasiya Fedorenko, CC BY-SA 3.0, Wikimedia Commons
12. He Wanted The Spotlight
As soon as he finalized the story, Stallone approached as many studios as he could to ask if they would buy the script, and he got a few bites. Producers Robert Chartoff and Irwin Winkler offered him $350,000 for the rights to Rocky, but there was one major roadblock. They had their own casting in mind, while Stallone stubbornly insisted he play the main role.
Thankfully, his script was so good, he had all the leverage he could hope for.
13. They Agreed To His Terms
In the end, neither Chartoff nor Irwin was as obstinate as Sylvester Stallone, and he negotiated until they allowed him to play the titular character of Rocky Balboa. This ended up being the best choice for them, as his performance launched him and the film into global stardom. In fact, famed critic Roger Ebert referred to him as the next Marlon Brando.
As the public flocked to the theaters, it was clear they felt the same.
14. He Was Memorialized
Upon its release, Rocky immediately became a worldwide phenomenon, but nowhere was the film celebrated more than the city in which it was set—Philadelphia. Here, Stallone’s iconic character received an impressive honor as the city built a statue of him at the entrance to the Philadelphia Museum of Art, whose steps feature prominently in the film.
This fame certainly helped during awards season.
15. He Was Praised
It was clear that audiences loved Rocky, but as awards season approached, the critical success of Stallone’s story and performance became even clearer. Nominated in both categories of Best Screenplay and Best Actor, he joined the club of only two other actors in history to achieve the same, Orson Welles and Charlie Chaplin.
Of course, this would also result in one of his most fateful encounters.
16. They Sat Together
While there’s no way he could have suspected it at the time, Sylvester Stallone was about to meet a man who would have one of the largest impacts on his career, all while at an awards show. In 1977, at the 34th Golden Globe Awards, Stallone attended since Rocky was up for awards in six categories, and his seat was at the same table as future fellow action star Arnold Schwarzenegger.
Supposedly, the actors quickly devolved into playground teasing.
State of California, Wikimedia Commons
17. He Laughed At Him
At the Golden Globes, Schwarzenegger won the New Star of the Year award for his film, Stay Hungry. This only stung more when Rocky lost five of its nominated awards and, according to Sylvester Stallone, Schwarzenegger outright laughed at him. Stallone didn’t let this go either, throwing a bowl of flowers at his rival when Rocky won its last nomination.
Although their conflict was just beginning, Stallone focused on his next project.
18. He Took Charge
Having gained experience as a celebrated actor and writer, Sylvester Stallone began his next project with a desire to have complete creative control. Taking the helm as writer, star, and director for the first time, he made the 1978 film Paradise Alley, which received mixed reviews. However, he had much greater success with the 1979 sequel to his original masterpiece, Rocky II.
Still, Rocky Balboa is far from Stallone’s only memorable character.
United Artists, Rocky II (1979)
19. He Became Another Icon
Stallone found more inspiration in the David Morell novel First Blood and felt so moved by it that he decided to adapt it to the screen. Again, taking creative lead—and liberties—he starred in the 1982 film of the same name, portraying the character of John Rambo, a Vietnam veteran who takes on the authorities of a small town.
With this release, it was finally time for Rocky Balboa to move over.
Philkon Phil Konstantin, Wikimedia Commons
20. They Loved Him
Sylvester Stallone made several changes from the original First Blood novel to his script, specifically concerning the character of John Rambo, but many considered this an improvement. According to critics, the book failed to imbue the character with the relatable humanity that Stallone did, which only earned him further applause.
While Rambo had made his impact, the world would never forget Rocky Balboa.
Orion Pictures, First Blood (1982)
21. He Was Committed
First Blood wasn’t Stallone’s only big release of 1982, as he also came out with the third installment of his now-iconic series, Rocky III. As he starred in both projects, he had to maintain the physique of both characters, spending six days each week at the gym until he supposedly reduced his body fat to a staggering 2.8%.
Furthermore, his enduring commitment didn’t end with these films.
United Artists, Rocky III (1982)
22. They Were His Characters
As the years progressed, Sylvester Stallone maintained this sort of partnership between his two most iconic characters, releasing both Rambo: First Blood Part II and Rocky IV in 1985. He wasn’t close to being done with these characters, and over the next decades, he would reprise these roles across a whopping 13 films in total.
Of course, since these were early action films, each one came with its own risks.
United Artists, Rocky IV (1985)
23. He Didn’t Expect It
Stallone had grown accustomed to putting his body under intense pressure for his roles, but one injury during production came as a surprise, especially since someone else inflicted it. While filming Rocky IV, he dared his co-star, Dolph Lundgren, to punch him in the chest as hard as he could. Stallone was clearly unprepared, as that one hit landed him straight in the hospital.
Meanwhile, his real-life rivalry was escalating with every passing year.
United Artists, Rocky IV (1985)
24. He Felt Insulted
It seems Arnold Schwarzenegger wasn’t ready to let go of his incident with Stallone, as became evident in 1985, when he spoke with tabloid paper The News of the World. During this interview, the topic of Stallone arose as both actors were quickly becoming Hollywood’s action guys. Much to Stallone’s later displeasure, Schwarzenegger claimed that his rival was prone to using body doubles in his movies.
Behind the scenes, Stallone’s romantic life was on the verge of a rough patch.
Gage Skidmore from Peoria, AZ, United States of America, Wikimedia Commons
25. He Found Someone Else
Although Sylvester Stallone and his wife, Sasha, stuck together through their difficult early years, he then became a superstar, and their relationship did nothing but sour. They divorced in February 1985, but by December, he was in another relationship. This marriage to actress Brigitte Nielsen was also short-lived, lasting only two years, during which the media constantly invaded their privacy.
Even after he failed another marriage, Brigitte was far from his last partner.
26. He Cheated On Her
Stallone got back into the dating game and began his relationship with model Jennifer Flavin, dating her from 1988 to 1994. They lasted longer than his previous marriage, but that didn’t exactly mean he was more committed. In fact, the whole reason for their breakup was his confession that he was also seeing another model named Janice Dickinson—who was allegedly pregnant with his child.
Concerning his other interpersonal conflicts, he started to play dirty.
Photographer: unclear Publisher: El Camino Real Charter High School, Wikimedia Commons
27. They Tried To Expose Him
By the late 1980s, Arnold Schwarzenegger was hot on Stallone’s tail to be Hollywood’s biggest action star, but little did he know, he was in for some bad publicity. In another article by The News of the World, the tabloid accused Schwarzenegger of sympathizing with Germany’s Third Reich, as his father had allegedly been instrumental in the atrocities of the holocaust.
Naturally, Schwarzenegger was fuming at these rumors.
Madison Square Garden Center, Wikimedia Commons
28. He Denied It
Two years after the article, the truth about Schwarzenegger’s family surfaced, revealing that the tabloid had cherry-picked their information and fabricated the rest. In reality, the Austrian actor’s father, Gustav Schwarzenegger, indeed had connections with Germany during WWII. However, being born two years after the end of WWII, Arnold was under no illusions and was never shy about his disdain for the Third Reich.
To make matters worse, he learned the source of this misinformation.
Mary Frampton, Los Angeles Times, Wikimedia Commons
29. He Was The Source
Understandably, seeing as the article’s writer, Wendy Leigh, had accused Schwarzenegger of being antisemitic and an admirer of Germany’s past Führer, the actor sued her for libel. By then, Leigh had revealed her source as none other than the Italian Stallion with a chip on his shoulder, Sylvester Stallone, who apparently paid for her litigation fees.
Even though Stallone was the instigator here, Schwarzenegger clearly lived in his mind rent-free.
30. He Was Petty
Sylvester Stallone proved he was willing to stoop to any level to antagonize Schwarzenegger, so it was obvious that the Terminator actor had gotten into his head. Stallone could barely even look at his rival, as he demonstrated one night when he demanded that the nightclub he was at take down a picture of Schwarzenegger they had on the wall, threatening to leave.
Stallone’s resentment was only made worse by his career’s clear decline.
Orion Pictures, Terminator (1984)
31. He Didn’t End On A High Note
As Stallone progressed into the 1990s, he went back to doing what he knew best and starred in Rocky V. This was truly a “full-circle” moment, as he not only brought in the director for the first film, John G Avildsen, but it was also meant to be the final Rocky film. However, upon its release, fans openly expressed their disappointment, and it was largely considered a failure.
Meanwhile, Schwarzenegger grew even more skilled at mind games.
Metro-Goldwyn-Mayer, Rocky V (1990)
32. He Tricked Him
Stallone’s box-office failures continued with his 1992 action-comedy, Stop! Or My Mom Will Shoot, his involvement in which led right back to Schwarzenegger’s meddling. Stallone had only taken the part to spite the Austrian actor, as he heard that Schwarzenegger was already interested. However, he later found out that Arnold had orchestrated the whole thing to goad him into doing an obviously doomed film.
Coincidentally, he was in for a much more personal rude awakening.
Universal Pictures, Stop! Or My Mom Will Shoot (1992)
33. She Was Wrong
Leaving his previous relationship with Jennifer Flavin, Stallone had proposed to Janice Dickinson, as they were confident she was carrying his baby. However, they encountered a twist when a DNA test revealed that he was, in fact, not the father. Seeing the whole thing as a huge mistake, Stallone immediately ended his engagement with Jennifer.
On the professional side of things, he wasn’t doing much better.
34. It Was Saved
For Stallone, the mid-1990s seemed to hold only more failure—at least in America. In the 1995 film Judge Dredd, he played the titular futuristic law enforcement officer, which most audiences in the US turned out to have no interest in. Fortunately for him, the film’s overseas reception was fantastic, and it only just earned back its $100 million budget.
Even more fortunately for him, his personal life was only getting better.
Buena Vista Pictures, Judge Dredd (1995)
35. He Made Another Commitment
While Stallone enjoyed a couple of relationships since his split with Jennifer Flavin, the reason they broke up no longer mattered, and they were both ready to start things up again. In 1997, after ensuring they were both in for the long run, Stallone and Jennifer finally married and would soon welcome the first of their three daughters.
Shockingly, this wasn’t the only relationship he repaired.
36. They Worked Things Out
It seems Stallone wasn’t the only one whose career was in decline, as even Schwarzenegger was experiencing a similar disheartening shift. Perhaps this was what finally gave them a real common ground, as the two began to patch things up. This turned into a professional relationship, and by 2000, word spread that they were working on a film together.
However, the new millennium didn’t bring much of an improvement.
Jack O'Quinn, Wikimedia Commons
37. He Became Worse
Now that he was in the 2000s, Stallone likely hoped to leave his series of box-office failures in the previous millennium, but it wasn’t meant to be. His first film of 2000, Get Carter, earned the now-familiar reception of disappointment and critical revile, and his next slate of movies over the following couple of years were no better.
Soon enough, though, dwindling box office numbers would be the least of his worries.
Warner Bros. Pictures, Get Carter (2000)
38. She Spoke Out
Suddenly, in 2001, Stallone’s name was being dragged through the mud, but not out of any professional rivalry. This was far more severe, as a woman named Margie Carr alleged that he forced himself on her the year before. Stallone’s lawyer immediately refuted her accusation, revealing that she had already sold her story to the tabloid Globe a month prior.
Seemingly unfazed, Stallone had no problem getting back to work right away.
39. He Redeemed It
For fans of the Rocky films, it was clear that the franchise had ended on a whimper, but Stallone was determined to change that. Taking back creative control over the story, he wrote, directed, and starred in the 2006 follow-up, Rocky Balboa. This film succeeded where its predecessor had failed, earning over double its $24 million budget domestically.
Ultimately, one character would always come first for him.
Metro-Goldwyn-Mayer (MGM), Rocky Balboa (2006)
40. He Made A Choice
Although their respective franchises hadn’t always been successful, by the late 2000s, Stallone had played both Rambo and Rocky enough to be synonymous with both. In 2008, though, one fan asked the difficult question of which character Stallone would most want to be remembered for, and since he viewed Rocky as his “first baby,” he chose the boxer.
At the same time, Stallone was already preparing for his next monumental project.
Yoni S.Hamenahem, Wikimedia Commons
41. He Had A New Project
Despite their intense rivalry, Stallone and Schwarzenegger were far from the only action heroes in the business, and it was time for a team-up. In 2010, Stallone put on all three of his filmmaking hats to create the massively successful ensemble film The Expendables, featuring other greats like Jason Statham, Terry Crews, and even Schwarzenegger himself.
These productions still carried a lot of risk, but this time, he couldn’t rely on his youth.
Lionsgate, The Expendables (2010)
42. He Was Injured
Although he was pushing 65 at the time of filming The Expendables, Stallone was still gung-ho to do many of his own stunts, much to his body’s detriment. One frightening incident landed him in the hospital with an implanted metal plate, after a scene with his co-star "Stone Cold" Steve Austin resulted in Stallone breaking his own neck.
But there were problems brewing elsewhere. All of a sudden, the public became aware of the drama within his family.
43. He Had Family Issues
Stallone was familiar with being in the public eye, but in 2013, the media aired out a brand new batch of his family’s dirty laundry. According to reports, back in the 1980s, Stallone was paying his half-sister, Toni-Ann Filiti, monthly payments and funding her psychiatric and medical costs. More suspiciously, she threatened to sue him on the grounds of mistreatment.
Instead, Stallone and his people turned the spotlight back on her.
Georges Biard, Wikimedia Commons
44. They Accused Her
Although Stallone appeased his half-sister by paying her a total of $2 million, his representatives still denied her accusations. Instead, they claimed that she was only blackmailing Stallone to feed her addiction to illicit substances, a story that even their own mother backed up.
Not long after, he was ready to bring his most iconic character into the modern day.
Patriarca12, Wikimedia Commons
45. He Came Back
Stallone had completed the Rocky franchise on a high note with Rocky Balboa, but he wasn’t content with that being the last time he portrayed the character. Eventually, in 2015, he returned to play the role again in the spin-off sequel Creed, directed by Ryan Coogler. While this may have felt like a big risk, both audiences and critics endlessly praised the film.
At the same time, Stallone once again faced a shocking controversy.
46. She Also Accused Him
Again in 2016, a report surfaced that brought Stallone into the light of bad publicity, but this time from the Las Vegas authorities. According to the report, while he was filming there in 1986, a 16-year-old girl accused him of forcing himself on her. However, nothing ever came of this, since Stallone denied everything, and his ex-wife, Brigitte, provided him with an alibi.
Even this horrific scandal wasn’t the last of its kind.
47. It Happened Again
Stallone hadn’t seen the last of these kinds of allegations against him, and in 2017, another woman accused him of grossly inappropriate actions. According to her, the incident had taken place in the 1990s at his office. However, his lawyers defended him by stating that she only filed the report against Stallone after failing to sell the story to an entertainment website.
Once again, the law was on his side.
Gage Skidmore , CC BY-SA 2.0, Wikimedia Commons
48. They Refused To Do Anything
The 2017 case launched a full investigation into the accusations against Stallone, but when all was said and done, he emerged from the scandal unscathed. The following year, the LA District Attorney's office announced that, since no witnesses to the incident could confirm the allegations, they would not be charging Stallone with anything.
Despite all of this controversy, his personal life had taken a positive turn.
nicolas genin, CC BY-SA 2.0, Wikimedia Commons
49. They Made Up
It turns out that, even after all the cheating and other relationship problems, Stallone and Jennifer Flavin’s marriage was going strong—until 2022, anyway. By that year, their relationship had deteriorated so much that Jennifer filed for divorce. However, before the end of the year, they worked their issues out and got back together.
In the most recent years, he unexpectedly took a much more unique position.
50. He Never Gave Up
While it was an enormous struggle, Stallone managed to carve out a legacy as one of the most iconic examples of a classic action movie star. From humble and challenging beginnings, he carved out a career as an underdog both onscreen and in his real life.
DominusVobiscum, Wikimedia Commons
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