Sylvester Stallone's Ex-Wives: How Many Times Has The Actor Been Married?

Sylvester Stallone is not only a talented actor, but he's also a lady's man. The "Rocky" actor has dated some of the most famous and beautiful women in the industry. He has sparked romances with Vanna White, Naomi Campbell, and Janice Dickinson, just to name a few. Stallone has fallen in love multiple times, and his love for more than one woman has had the actor walk down the aisle several times.

However, Stallone never intended to say "I Do" more than once. The "Creed" actor grew up in a broken home himself. According to Biography, his parents had a tumultuous relationship that lasted a while before they decided to get a divorce. Seeing his parents' relationship, Stallone realized that he wanted a forever type of love. The actor once shared, "It took me a long time to be convinced that marriage was right for me because I've come from a long line of broken marriages."

Even with his protective mindset on marriage, Stallone couldn't help but fall in love not once, not twice, but three times. That's right! The actor has been married to three women in his lifetime. Although this seems like the norm in Hollywood to get married more than once, it's never what the actor pictured. But sometimes life throws a rock that shatters your plans, and for Stallone, it threw a couple.

Sylvester Stallone first tied the knot in 1974 to photographer Sasha Czack. From marriage to babies, the couple welcomed two sons into their lives, Sage and Seargeoh. The pair seemed to have the life everyone would want. That all changed as Stallone garnered more fame. According to UPI, the actor ended up cheating on Czack. He revealed, "I yielded to temptation. I was seduced. I explored my every fantasy. ... I have regrets, but I don't hold myself in contempt." Although Stallone and Czack tried to get back together, the damage had been done. After ten years of marriage, the couple called it quits in 1985.

As if the affair wasn't a tough blow for Czack, just months after they separated, Stallone was already walking down the aisle with Brigitte Nielsen. According to The Guardian, Stallone and Nielsen met after she sent the "Tulsa King" actor a provocative photo to his room. The two were still married, but that didn't stop their romance. And as soon as Stallone ended it with Czack, he and Nielsen were tying the knot. The couple's whirlwind romance didn't last long, as they were married for less than two years. Nielsen told The Guardian, "It was a horrible marriage." The couple had nearly a twenty-year age gap, so it's not surprising they didn't see eye to eye. The two failed marriages, however, didn't stop Stallone from falling in love for a third time.

After Sylvester Stallone divorced Brigitte Nielsen in 1987, the "Rocky" actor crossed paths with a young Jennifer Flavin in 1988. The pair hit it off, and it wasn't long before they were in a full-blown relationship. After breaking up and reconciling years later, The couple welcomed their first daughter, Sophia, before they tied the knot shortly after. The actor shared with People, "I have had two great things happen to me in the past year: the birth of our beautiful daughter Sophia Rose and now my marriage to Jennifer, who is a great mother and I know will be a wonderful wife." Their love continued to grow as Stallone and Flavin welcomed two more daughters. It seemed like Stallone had finally found the one, and as they say, the third time was the charm.

But, behind closed doors, you never truly know what a marriage is like. And Stallone nearly ended up with a third ex-wife. According to People, in August 2022, Flavin filed for divorce from the "Tulsa King" actor. Flavin shared, "I'm sad to announce that after 25 years of marriage I have filed for divorce from my husband Sylvester Stallone. While we will no longer be married, I will always cherish the more than 30-year relationship that we shared..." While it seemed like Stallone would add another divorce to the books, the couple reconciled just a month later and have been doing great ever since.