“Happy 25th anniversary to my amazing wife,” Sylvester Stallone wrote on May 17, 2022. In the Instagram post, the then-75-year-old actor posed alongside his wife, Jennifer Flavin. The Instagram Gallery showed Sly and Jennifer together throughout the years. “There [are] not enough words to describe what this incredibly selfless dedicated [and] patient woman has meant to our lives, and I only wish they could be another 25! Thank you, sweetheart!”
However, Jennifer hasn’t been the only woman to bear the title of “Mrs. Sylvester Stallone.” Two other women – Sasha Czack and Brigitte Nielsen – have walked down the aisle with the Rambo superstar. Here’s what you need to know about his current wife and his previous marriages.
Sylvester first met Jennifer in 1988, when she was a 19-year-old Valley Girl visiting Hollywood, according to PEOPLE. She met Stallone, who was in his early 40s, at a restaurant. But, there was an attraction, and by 1990, the two went public with their romance at a Los Angeles event.
The early days of the marriage were a bit rough. Stallone broke up with her via FexEx, per People. “He sent me a six-page handwritten letter, in pen,” she said in a 1994 interview. “It was pretty sloppy.” Jennifer later found out Stallone had dumped her because he was having an affair with supermodel Janice Dickinson.
Janice gave birth to a girl, and Sylvester was heavily rumored to be the father. “It hit me like a ton of bricks,” Flavin told PEOPLE. “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.” However, a paternity test revealed that Sylvester wasn’t the father, and he ended the relationship.
Sly and Jennifer reconciled in 1995. They welcomed their first child, Sophia Rose Stallone, in 1996. The following year, they tied the knot at a civil ceremony at The Dorchester Hotel in London, per PEOPLE. A more elaborate chapel ceremony at Blenheim Palace in Oxfordshire followed. Only a few people attended the event, and despite Stallone’s history of infidelity, it seems the arrival of Sophia set him straight.
The couple welcomed daughter Sistine Rose in 1998 and Scarlet Rose in 2002. Twenty years after Scarlet’s arrival, Jennifer and Sylvester commemorated twenty-five years as man and wife.
“Third time’s the charm” seems to apply to Stallone’s married life. His first marriage came when he tied the knot with photographer Sasha Czack in December 1974. They divorced in February 1985. Over that decade together, the two welcomed sons Sage Stallone (who died of heart disease at age 36 in 2012) and Seargeoh.
Stallone’s marriage to Czack was a rocky one. He walked out on her following Paradise Alley in 1978. “I had discovered real fear for the first time,” he told Rolling Stone in 1982. “Fear of losing what I had attained. Before, I didn’t care. I was broke.”
“I became a [recluse],” Sylvester said, adding that he resented his family and had an affair. “But the most drastic change was my values. I really became envious and coveted other people’s success. In doing all that, I got so far away from whatever it took, like talent, to do Rocky, I thought I’d lost it all. I thought that I couldn’t regain any kind of momentum again. I felt I was really slipping down.”
While married to Sasha, Sylvester began a public affair with Susan Anton. He and Susan broke up, and Sylvester started missing his wife and kids. Before taking him back, Susan told Sylvester to get his personal demons and existential crisis under control. “She knew that if I came back at that time that eventually I would leave again. In other words, there was too many loose ends. Go out and solve the mystery,” he said.
While Sasha and Sly reconciled, their marriage didn’t outlast the 1980s.
Sylvester Stallone divorced Sasha Czack in February 1985. By December 1985, he was married to Brigitte Nielsen. Brigitte reportedly introduced herself to Sly by sending a provocative photograph of herself to his hotel room, the 1980s equivalent of air-dropping a pic. Brigitte was married to Danish musician Kasper Winding, and Stallone was still married to Sasha. But, once both Sly and Brigitte finalized their respective divorces, they tied the knot.
The union lasted about 19 months. “It was a horrible marriage,” she told The Guardian in 2019. He was almost twice her age, and the gap was too wide for them to cross. “Everybody looks at you as a villain,” she told The Guardian. “After I left Sylvester, I kind of felt like I was blacklisted for a long time. I am almost positive that had I not been in the public eye with this famous man, that would never have happened. But they always thought: after Stallone, who is going to be next?”
During this disastrous marriage, Nielsen portrayed Ludmilla Drago, wife of Ivan Drago (Dolph Lundgren), in 1985’s Rocky IV. She reprised the role in Creed II, 33 years after first playing the character. “My heart was beating very fast,” she told PEOPLE about the first day of filming the boxing epic.
“In 1985, I was married to Sylvester, and this time I am the ex-wife,” she said. “But it was wonderful to have half of the cast there 32 years later. Who could have ever dreamed that you pick up the same roles many years after?”
As for how the two made this sequel work? “We are two professionals, and we kept it that way,” she said. “He stayed in the American corner, and I stayed in the Russian corner. We were on opposite sides, but it was pleasant.”