By Wonderwall.com Editors 12:30pm PST, Nov 14, 2022
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Sylvester Stallone has been a Hollywood star for more than five decades! To celebrate the release of his latest project — the Paramount+ series "Tulsa King" — on Nov. 13, 2022, Wonderwall.com is going all the way back to the beginning of an unlikely story: Italian American kid fights his way up from the streets to become a box office superstar. Keep reading to relive Sly's life and career in photos from "Rocky" to "Rambo" and everything since…
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Michael Sylvester Gardenzio Stallone was born in New York City in 1946 to a hairdresser father and a women's wrestling promoter mother. Doctors used forceps at his birth and partially paralyzed one side of his face. That trademark drawl so often imitated — "Yo, Adrian!" — has been with him his whole life. Sly — seen here in 1972 — also suffered from other health problems as a child, including rickets. His parents divorced in 1957 and he moved with his mother to Philadelphia.
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Sylvester Stallone had a tough start to his acting career. In 1970, he was so broke that he was sleeping in the New York Port Authority bus station. Out of desperation, he acted in a soft-core adult film called "The Party at Kitty and Stud's." It came back to haunt him later when it was renamed "The Italian Stallion" to cash in on his success. He landed small parts in movies throughout the '70s, including "The Lords of Flatbush" — seen here — with Henry Winkler in 1974.
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In December 1974, 28-year-old Sylvester Stallone married 24-year-old Sasha Czack. The couple, seen here in 1977, welcomed son Sage Moonblood in 1976 and a second son, Seargeoh, in 1979.
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Sylvester Stallone and his family — wife Sasha Czack and son Sage Stallone — are pictured here at a Las Vegas boxing match at Caesars Palace in 1982.
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Sylvester Stallone only had a hundred bucks in the bank — and his wife, Sasha, was pregnant with son Sage — when he saw a Muhammad Ali fight on TV and got the idea for the 1976 film "Rocky." With that underdog movie based on the lives of his boxing heroes — which he wrote and starred in — Sly blew the top off Hollywood. "Rocky" went on to gross $225 million (the equivalent of $967 million today). Of course, Sly also did something more impressive by Hollywood standards: He created a movie franchise that would span decades.
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At the Oscars in 1976, "Rocky" cleaned up. The film won three statues including best picture, best director and best editing, and Sly got a nomination for best actor and best screenplay. And all this just a year after he played Machine Gun Joe Viterbo in the B-movie classic "Death Race 2000."
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Sylvester Stallone experienced no sophom*ore slump: He ended the '70s by directing his first film — "Rocky II" — and started the '80s by kicking off his next gigantic franchise, 1982's "First Blood." With his portrayal of Vietnam veteran John Rambo, Sly again won a huge audience as he began morphing into a world-class action star. He also transformed geopolitics: Ronald Reagan received the nickname "Ronbo" in honor of the character. "First Blood" was a critical and commercial success, grossing $125.2 million at the box office.
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In 1982, Sylvester Stallone starred in "Rocky III," which earned $270 million. One year later, Sly directed John Travolta in 1983's "Staying Alive," the sequel to "Saturday Night Fever." (The men are seen here at its July 1983 premiere.) The disco movie was a critical failure but audiences loved it. "Staying Alive" grossed over $127 million worldwide against its $22 million budget.
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Sylvester Stallone also cast his little brother, Frank Stallone, as the character Carl in "Staying Alive." The brothers are pictured here in a fun family portrait in 1983 around the time of the movie's premiere.
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In 1984, Sylvester Stallone was honored with a star on the Hollywood Walk of Fame alongside his "Rhinestone" co-star Dolly Parton.
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Sylvester Stallone and wife Sasha Czack split in late 1984 — just a few months after attending the "Ghostbusters" premiere together (seen here) — after a decade of marriage. They divorced on Feb. 14, 1985. The Italian Stallion wouldn't stay single for long, however…
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Fresh off the heels of his divorce, Sylvester Stallone brought John Rambo back to the big screen with the 1985 sequel "Rambo: First Blood Part II," which grossed a remarkable $300 million. And it wasn't his only blockbuster that year…
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Sylvester Stallone starred in "Rocky IV" (with then-newcomer Dolph Lundgren as his Soviet opponent) in November 1985. It was a huge hit that grossed more than $300 million — more than any other "Rocky" movie at the time.
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Sylvester Stallone was 39 when he married 6-foot-1 Danish actress Brigitte Nielsen — his 22-year-old co-star in "Rocky IV" — in December 1985, 10 months after he divorced his first wife. The marriage only lasted 19 months and their messy breakup dominated tabloid headlines. "The biggest misconception while I was with Sylvester was the fact that everybody thought I married him because of money," Brigitte later told Oprah Winfrey. "They didn't understand that he begged me to marry. He begged me!"
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Sylvester Stallone found love once again when he met model Jennifer Flavin at a Beverly Hills restaurant in 1988. The couple are seen here that August.
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Sylvester Stallone teamed up with Kurt Russell for the well-received 1989 buddy-cop movie "Tango and Cash."
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Sylvester Stallone's oldest son, Sage Stallone, starred in 1990's "Rocky V" as Rocky's son. "Rocky V" didn't fair as well as its predecessors but still grossed $119 million at the box office.
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Sylvester Stallone also focused on another of his talents in the early '90s: painting. The Italian Stallion began painting in the 1970s and has since produced hundreds of works. Sly is pictured here at an art exhibit of his paintings at Hanson Galleries in Beverly Hills in 1990.
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Sylvester Stallone experienced a serious career slump in the early 1990s. He starred in "Rocky V," "Oscar" (pictured) and "Stop! Or My Mom Will Shoot" — all critical and commercial disasters. Luckily, he had another project to keep him busy…
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In 1991, the Planet Hollywood franchise was born, with action stars Sylvester Stallone, Arnold Schwarzenegger and Bruce Willis as its most notable investors. It might not have had the success of the Hard Rock Cafe, which it imitated, but it kept Sly in the headlines during a career lull.
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Sylvester Stallone didn't attend the 1991 Planet Hollywood grand opening in New York alone! He brought then-girlfriend Jennifer Flavin along.
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Sylvester Stallone experienced a career comeback in the mid-1990s with box office successes "Cliffhanger" (pictured) and "Demolition Man" in 1993 and "Judge Dredd" in 1995. All three movies grossed over $100 million and re-established Sly as the action star we've come to know and love.
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Sylvester Stallone brought his mother, Jackie Stallone, to the premiere of "Daylight" at Mann's Chinese Theatre in Hollywood in 1996.
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Sylvester Stallone and Jennifer Flavin married in May 1997 — they're seen here a few months later — after nearly 10 years of dating. The couple welcomed their first daughter, Sophia, one year earlier and soon added two more daughters, Sistine and Scarlet, to the bunch.
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In 1998, Sylvester Stallone attended a Planet Hollywood party during the 51st Cannes Film Festival.
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The early 2000s didn't offer much career-wise for Sly, who had a role in "Spy Kids: 3-D" and also made a brief foray into reality TV in "The Contender" with boxing legend Sugar Ray Leonard. He only co-hosted the NBC show for one season before leaving to focus on "Rocky" and "Rambo" reboots.
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Refocusing on his popular franchises paid off for Sylvester Stallone. The 2006 reboot "Rocky Balboa" was a critical darling that earned $155 million worldwide. The 2008 movie "Rambo" performed just as well, grossing over $113 million. Sly is pictured here at the "Rocky Balboa" premiere with his wife, Jennifer Flavin, and their three daughters, Sophia, Sistine and Scarlet.
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Sylvester Stallone launched yet another super-successful movie franchise in 2010. "The Expendables" starred nearly all of the popular action-hero actors from the '80s and '90s (including Arnold Schwarzenegger and Bruce Willis, seen here with Sylvester at the movie's Hollywood premiere) and audiences couldn't get enough. The film, which Sly directed, wrote and starred in, earned over $274 million and spawned two sequels with another one in the works.
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In 2011, Sylvester Stallone was inducted into the International Boxing Hall of Fame. "I've never pretended to be a boxer. I don't possess those skills," he said, as reported by SylvesterStallone.com."What I do think I have is an understanding of what goes on outside the ring. Outside the ring is sometimes maybe an even bigger struggle than what goes on inside the ring, and I was able to capture that."
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In July 2012, Sylvester Stallone's son Sage was found dead in his Los Angeles home. Despite speculation about possible drug abuse, an autopsy found that the 36-year-old actor and film producer had died of a heart attack resulting from atherosclerosis. Six weeks later, Sly's half-sister, Toni Ann Filiti, died of lung cancer. Sly, pictured here with Sage at the "Rocky Balboa" premiere in 2006, channeled his grief into his next movie, "Creed."
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In 2015, Sylvester Stallone produced and starred in the "Rocky" spinoff and sequel "Creed." The film, which starred Michael B. Jordan as Adonis Johnson Creed, Apollo Creed's son, received critical acclaim upon its release. "Creed" gave Sly (seen here with Michael at the movie's Los Angeles premiere that November) his second Oscar nomination — his first nod since the original film — and a Golden Globe win. He made sure to acknowledge his late son, Sage, while accepting his award for best supporting actor. "Any time you can vent emotions that are real is very helpful," he told the audience. "Most importantly, I wanted to respect his memory and I think we have done that. It was good."
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Sylvester Stallone and Michael B. Jordan are seen here in 2015's "Creed." In 2018, while speaking with Vanity Fair, Michael B. Jordan shared some advice he received from his veteran co-star. "He said to me, 'Mike, don't try to copy what I did. You are Creed. You own it. Don't worry about having to live up to any expectations or the legacy of the movies. Put in the hard work, but also have fun,'" he shared. Michael commended Sly, adding, "He gives so much to you. When you are shooting a scene with him, he allows you to respond. He gives you respect. He looks at you as a partner. It was a real collaborative process."
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In 2016, Sylvester Stallone won his first Golden Globe Award. He took home the honor for best supporting actor for his performance as Rocky Balboa in 2015's "Creed."
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Two icons together! In November 2016, martial artist and action-comedy film star actor Jackie Chan received an Honorary Oscar for his "extraordinary achievements" in film during the Academy of Motion Picture Arts and Sciences' Eighth Annual Governors Awards. After Sylvester Stallone recorded Jackie's speech on his iPhone while seated in the audience, he posed for a photo with the Hong Kong native to commemorate the occasion.
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In 2017, all three of Sylvester Stallone's daughters made Golden Globes history when they were collectively named Miss Golden Globe. Sistine Stallone, Scarlet Stallone and Sophia Stallone are pictured here with their parents, Sly and Jennifer Flavin, at the 2017 award ceremony. "Except for Sistine [who's a model], we've never really been in the public eye," Sophia told The Hollywood Reporter. "Everyone else who has famous parents, they're always in the public eye. But my mom was very about education, staying grounded, family — we always eat dinner together." Added Scarlet: "And so this is our moment: the Golden Globes."
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Sylvester Stallone reprised his role as Rocky Balboa alongside Michael B. Jordan in the 2018 film "Creed II." The "Rocky" spinoff earned more than $214 million at the box office.
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At the Cannes Film Festival in France on May 24, 2019, Sylvester Stallone — with wife Jennifer Flavin and actress daughter Sistine Rose Stallone by his side — was feted with an honorary career retrospective that culminated in a first look at the trailer for 2019's "Rambo: Last Blood," the fifth installment in the franchise and one of the first films Sly produced under his new Balboa Productions banner. A year earlier in 2018, the actor-writer created his own film studio, Balboa Productions, in collaboration with film producer Braden Aftergood.
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In September 2019, Sylvester Stallone starred in "Rambo: Last Blood," the fifth film in the "Rambo" action-movie franchise. But don't worry, "Rocky" fans — Sly hasn't forgotten about the character that made him famous. The same year, he announced that a "Rocky" sequel and prequel were in development and revealed there were ongoing discussions about a "Rocky" prequel TV series, which would air on a streaming service.
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Sylvester Stallone has never gave up creating art through outlets other than his movies. "You know, maybe I should have been a painter," he told The Hollywood Reporter in December 2021 as he opened the largest-ever retrospective of his paintings, spanning the 1960s to the present, at the Osthaus Museum Hagen in Hagen, Germany. "It sure would have meant a lot less stress."
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Sylvester Stallone joined the streaming world! He's seen here in May 2022 in character as Dwight Manfredi, a New York Mafia figure who's relocated to Tulsa, Oklahoma, after serving a 25-year prison sentence, on the set of his Paramount+ series "Tulsa King," a crime drama from "Yellowstone" creator Taylor Sheridan that debuted in November 2022.
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In August 2022, Jennifer Flavin — Sylvester Stallone's wife of more than 25 years with whom he shares daughters Sistine, Sophia and Scarlet — filed to divorce the action star in their new home state of Florida. However, a month later, the longtime couple reconciled. Sly (seen here with his wife, a former model, at a fashion show in October 2022 a few weeks after she withdrew her divorce petition) later told The Hollywood Reporter he was to blame for almost ruining his marriage. "Sometimes I put the work ahead of [my family], and that is a tragic mistake which won't happen again," he said.
