Sylvester Stallone’s Romantic History Is Messy AF

Sylvester Stallone has a thing for models… which has gotten him into some trouble over the years.

His wife Jennifer Flavin, who is filing for divorce after 25 years of marriage, is a former model. And back in the ’80s, their relationship got off to a very ROCKY start. (Get it?)

A Family Tragedy

Sylvester Stallone married the aspiring actress Sasha Czack in 1974. He was 28 years old. It was Czack who stood by Stallone during the depths of his pre-Rocky poverty, waiting tables to support them and assisting him with the screenwriting process. After gaining attention on the soap opera Love For Life, according to some sources, Czack was even offered the lead role in Play It As It Lays, Joan Didion’s 1972 film. But Czack turned down the role in order to stay with Stallone in New York City.

Eventually, the struggle paid off. While with Czack, Stallone wrote — and starred in and directed — the original Rocky. When it premiered in 1976, the sports drama was an unmatched box office success that would spawn a nine-movie franchise.

But trouble was on the horizon for Czack and Stallone. They went on to have two sons together: Sage Moonblood Stallone, born in 1976, and Seargeoh Stallone, born in 1979. Seargeoh was diagnosed with autism at an early age and despite pressure to send him to an institution (it was the ’80s), the couple decided to raise Seargeoh, privately, at home. But due to his work, Stallone simply could not be around.

“We both broke down [at the diagnosis]. I knew that Sly couldn’t get as involved because of his work. We do what we have to do. So I just said, ‘Give me the money, and I’ll take care of it,'” Czack told People in a rare interview. Eventually, that division of labor took a toll on the marriage. But the real kicker was Stallone’s extramarital affair with singer Susan Anton. He and Czack divorced in 1985.

Over the years, Sage remained a more public figure than both his mother and brother. But in 2012, tragedy struck. Sage died of a sudden heart attack in his Los Angeles home. He was 36 years old.

Marriage to Brigitte Nielson

The Danish beauty Brigitte Nielsen made a name for herself as a model during the early ’80s; she was photographed by legendary photographers Greg Gorman and Helmut Newton and even posed for Playboy.

Then, in 1985, she transitioned into acting, first appearing alongside Arnold Schwarzenegger in the fantasy Red Sonja. During that production, Nielson began an affair with Schwarzenegger soon after he began dating Maria Shriver. Schwarzenegger confirmed this in 2020… perhaps that’s why Sylvester Stallone and Schwarzenegger always hated each other?

It appears that Nielson was already involved with Stallone at that time. The two became engaged the following year while filming Rocky IV — Nielson played Ivan Drago’s wife. They wed after the film’s released and appeared in one more movie together, Cobra, before splitting in a highly publicized divorce. Their marriage lasted only two years.

In 2018, they reunited on-screen after more than 30 years for Creed II.

The Janice Dickinson Affair

Oh, Sly, you sly dog…

In 1988, the 47-year-old Sylvester Stallone met his future (ex) wife Jennifer Flavin at a Beverly Hills restaurant. Flavin was a young, up-and-coming model and then they dated until 1994, when Stallone dumped her unceremoniously in a “sloppy,“ handwritten letter delivered via FedEx. That’s right. Dumped by FedEx. But why?

Apparently, Stallone’s secret girlfriend was pregnant. And the sidepiece was none other than supermodel Janice Dickson. Stallone decided to end things with Flavin when he learned Dickinson was with child. But in his rambling letter, Stallone did not reveal the affair or Dickinson’s pregnancy. Instead, Flavin learned the heartbreaking news at work, through the modeling agency grapevine.

Dickinson gave birth to a baby girl, Savannah Rodin, that year and she was briefly engaged to Stallone. But when a paternity test revealed Stallone was in fact not the father, they broke up.

After that, Stallone became briefly engaged, again, to another model: Angie Everhart.

The Boob Job Debacle

During their short engagement, Angie Everhart alleges that Stallone convinced her to get a boob job — then bungled the procedure. According to Everhart, Stallone entered the operation room after she was unconscious and told the surgeon, Dr. Steven Hoefflin, to increase the size up to Double-Ds: “Big but perky, kinda like a 17- year-old.” is the disturbing request that staff member Barbara Maywood recalls.

Hoefflin agreed to Stallone’s order and Everhart left her star boyfriend as a result. Since then, she’s suffered a myriad of health issues stemming from the botched boob job and speaks only about the potential complications of going under the knife. Everhart also believes the breast enlargement hurt her career as a model.

Life with Jennifer Flavin

Following the split from Angie Everhart, Sylvester Stallone returned to ex-Jennifer Flavin with his tail between his legs. And after some serious wooing, she took him back. The couple wed in 1997 and had three daughters together: Sophia Stallone, Sistine Stallone, and Scarlet Stallone. For 25 years, they remained one of the most recognizable Hollywood households. A reality show centering around the Stallones is even slated for a future release on Paramount+.

So the world was shocked when Flavin filed for divorce on August 19, 2022, accusing Stallone of moving assets from their marital funds. For his part, Stallone has spoken up, saying, ” “We just went in different directions. I have the highest respect for Jennifer. I will always love her. She’s an amazing woman. She’s the nicest human being I’ve ever met.” He also went out of his way to dispel rumors that Flavin was leaving over a fight about owning a Rottweiler: “We did not end the relationship on such a trivial argument.”

But even before the dog rumors and financial squabbles came to light, there was trouble in paradise.

Sex Crime Allegations

In 2001, a stripper named Margie Carr came forward saying she and Sylvester Stallone had a 10-year affair during which he raped her, in 2000, at a Santa Monica gym. Stallone’s camp denied Carr’s claims and it appears the lawsuit was eventually dropped.

Then, in 2016, a report from the Las Vegas Metropolitan Police Department was made public implicating Stallone in the sexual assault by a 16-year-old girl while filming in Las Vegas in 1986. According to the report, the teen said Stallone, who was 40 at the time, forced her to have a threesome with him and his bodyguard. A representative of Stallone denied the allegation, though, and was backed up by Brigitte Nielsen. Nielsen said that she was with him at the time of the alleged incident.

The following year, another (unnamed) woman accused Stallone of sexual assault, saying he attacked her at his Santa Monica office during the early ’90s. Stallone denied the claim and his attorneys said Stallone once had a consensual relationship with the accuser. However, in 2018, the Los Angeles District Attorney’s office confirmed they were investigating Stallone though charges were never pressed.