The Most Unexpected Breakups: Celebrity Marriages That Ended After Decades

Having a lot of miles on the car isn't necessarily insurance that long-married couples such as Sylvester Stallone and Jennifer Flavin will want to keep traveling the same road together forever.

By Natalie Finn Sep 25, 2022 12:00 PMTags
Watch: Sylvester Stallone & Jennifer Flavin Divorce After 25 Years

Sylvester Stallone and Jennifer Flavin celebrated their 25th wedding anniversary expressing the utmost optimism.

"There is not enough words to describe what this incredibly selfless dedicated, patient, woman has meant to our lives and I only wish they could be another 25!" Stallone wrote on Instagram May 17. On her end, Flavin noted, "Our marriage keeps getting better every year! I can't wait to spend the rest of our lives together."

Instead, she filed for divorce in August. (And deleted that anniversary post.)

"I love my family," Stallone stated Aug. 24. "We are amicably and privately addressing these personal issues." He's shared nothing but glowing sentiments about the mother of his three daughters since, and that somewhat cryptic first comment has led hopeful fans to wonder if perhaps their differences are reconcilable. (And his anniversary sentiments remain live.)

Still, what a jarring reminder that even the long celebrity marriages we tend to treat as givens could go at any time.

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2022 Celebrity Breakups

Basically, as years go by you just get used to certain people being together, which is why every time a famous couple with a two-digit anniversary calls it quits, it can feel like an affront to love itself.

Because when the latest hot duo break up after a few months and then relationship mitosis leads to them becoming halves of two more hot couples, and so on, you can chalk it up to those people just not being right for each other in the long run.

But what if there's already been a long run? Was most of that time happy and then it just wasn't—or is the opposite the case, and signing those papers calls for champagne?

For our very scientific purposes, celebrities have provided all sorts of specimens for observation, and here's a sampling of couples who parted ways after decades, for whatever reason:

Tom Brady and Gisele Bündchen

The NFL star and the supermodel touched down in divorce court after 13 years of marriage, confirming Oct. 28, 2022, on their respective social media platforms that they had finalized the terms of their split.

"We arrived at this decision amicably and with gratitude for the time we spent together," Brady, who shares kids Benjamin, 12, and Vivian, 9, with Bündchen, wrote in his Instagram Story message. "We are blessed with beautiful and wonderful children who will continue to be the center of our world in every way. We will continue to work together as parents to always ensure they receive the love and attention they deserve."

The Super Bowl MVP noted that he and Bündchen didn't arrive at this decision lightly. "Doing so is, of course, painful and difficult, like it is for many people who go through the same thing every day around the world," he continued. "However we wish only the best for each other as we pursue whatever new chapters in our lives that are yet to be written."

Sylvester Stallone and Jennifer Flavin

Just three months after their 25th wedding anniversary, Flavin filed for divorce on Aug. 19, 2022, triggering a host of rumors about potential trivialities that could have inspired her decision.

Stallone nipped one in the bud—they didn't have a falling-out over what kind of dog he wanted to get—and told TMZ, "I will always love her. She's an amazing woman. She's the nicest human being I've ever met."

He also said in a statement at the time, "I love my family. We are amicably and privately addressing these personal issues."

The parents of three daughters—Sophia, 26, Sistine, 24, and Scarlet, 20—have since put up a united front on social media, prompting hopes that the Rocky star and his bride maybe just needed time in their respective corners to regroup.

Tish and Billy Ray Cyrus

The parents of daughters Miley, 29, and Noah, 22, and son Braison , 28 (plus he adopted her daughter Brandi and son Trace, 33), tied the knot in 1993.

The country superstar filed for divorce in 2010, saying in a statement at the time that they were "trying to work through some personal matters." Mission accomplished, at least temporarily, because Cyrus withdrew his petition in March 2011. He refiled in June 2013, however, and she counter-filed. And yet they again decided to stay together, Tish crediting couples therapy for bringing them closer. 

But Tish filed for divorce again in April, her petition stating that she and her husband of 29 years had been living apart since February 2020.

"It is after 30 years, five amazing children and a lifetime of memories, we have decided to go our separate ways—not with sadness, but with love in our hearts," the friendly exes told People in a joint statement. "We have grown up together, raised a family we can be so proud of, and it is now time to create our own paths."

In November 2022, Billy Ray's rep confirmed he was engaged to singer Firerose, and Tish accepted Prison Break star Dominic Purcell's proposal in April 2023.

Bill and Melinda Gates

The parents of three and co-founders of the internationally renowned Bill and Melinda Gates Foundation revealed in May 2021 they were splitting up after 27 years of marriage. A Washington judge finalized their divorce just three months later, a ready-to-roll separation contract making the division of their estimated $130 billion fortune less onerous.

But in the interim, the Wall Street Journal reported that she had started meeting with divorce lawyers as early as May 2019, and reasons why being married to the co-founder of Microsoft wasn't all it was cracked up to be started to emerge.

Sean Penn and Robin Wright

Both recently divorced, Penn from Madonna and Wright from Dane Witherspoon, the actors fell in love making the 1990 crime drama State of Grace. They welcomed daughter Dylan in 1991 and son Hopper in 1993 and then decided to tie the knot in 1996. They purposely moved to Northern California to raise their kids away from "the bubble of celebrity," Wright told Vanity Fair in 2015, but tumult followed and, after a few false starts, they officially divorced in 2010.

"I believe we were together not only to have our beautiful children but to learn how to love...for the next time around, the right way," the House of Cards star said. "And then, what I'm looking for in people now is kindness."

At the time she was back on with ex-fiancé Ben Foster, but after that ended she moved on with Clement Giraudet, marrying him in 2018. TMZ reported Sept. 24 that Wright has filed for divorce, citing July 31, 2022, as their date of separation.

Penn famously dated Charlize Theron for a couple of years and then married Leila George in January 2020, but she filed for divorce in October 2021.

Arnold Schwarzenegger and Maria Shriver

The power couple—and that was even before they were governor and first lady of California—announced in May 2011 that they had separated after 25 years of marriage.

A week later, Schwarzenegger came clean about fathering a son with his family's former housekeeper of more than 20 years. Joseph Baena, 25, enjoys a relationship with his dad (as well as an affinity for the weight room) and is pursuing his own career as an actor.

The Shriver-Schwarzenegger union, which produced daughters Katherine, 33, and Christina, 31, and sons Patrick, 29, and Christopher, 24, didn't officially end until December 2021, when the grandparents of two finalized their divorce.

Teresa and Joe Giudice

His-and-hers prison sentences for fraud were not kind to the Real Housewives of New Jersey stars' 20-year marriage. He ended up being deported to Italy after spending three years behind bars, and they divorced in September 2020.

"I can't get mad at her," Joe told E! News of his ex a month later. "She's the mother of my four daughters and she's taking care of them right now because obviously I can't. What am I going to do, have the kids move here to a country that they don't even know the language? That would be a disaster...Thank God they're tough kids, but it's still a damn shame. At the end of the day, you know, we're doing our best."

Teresa is once again a married woman, wedding Luis Ruelas in August 2022, the couple having met in a chance encounter at the Jersey shore. The bride's four daughters—Gia, 22, Gabriella, 19, Milania, 17, and Audriana, 13—were all in attendance. 

Susan Sarandon and Tim Robbins

Married for all intents and purposes, if not on paper, the Oscar winners separated in the summer of 2009 after 23 years together, having met making the rowdy 1988 baseball romance Bull Durham.

They share sons Jack, 33, and Miles, 31, plus Robbins helped raise Sarandon's daughter, Eva Amurri, 38.

"People were coming up to me in the street and saying, 'I cried and cried when I heard,'" Sarandon told The Telegraph in 2010 after their breakup. "Well, I was sadder! I didn't think it would ever happen, either. You bring people into your life at certain times. Maybe you have a relationship to have children and you realize that it's fulfilled after that point."

Robbins ended up marrying actress Gratiela Brancusi in 2017, but it wasn't widely known they'd taken that step until he filed for divorce in January 2021.

Mel Gibson and Robyn Moore

Though she didn't file for divorce from the father of her seven children until April 2009, according to Reuters, their separation began just days after his explosive drunk-driving arrest in July 2006.

"Throughout our marriage and separation we have always strived to maintain the privacy and integrity of our family and will continue to do so," they said in a 2009 statement confirming the end of their union. At the time, Gibson was already expecting a child, his eighth, with then-girlfriend Oksana Grigorieva. (He's since become a dad of nine, welcoming son Lars in 2017 with Rosalind Ross.)

"It was an unfortunate incident," Gibson said on Variety's Playback podcast in 2016, referring to his 2006 arrest and the resulting backlash over anti-Semitic comments he made to the officer that pulled him over. "I was loaded and angry and arrested. I was recorded illegally by an unscrupulous police officer who was never prosecuted for that crime...So, not fair. I guess as who I am, I'm not allowed to have a nervous breakdown, ever."

Kody and Christine Brown

The TLC star's third of four "sister wives"—and mother of six of his 18 children—left the family's Arizona home in November 2021 after 27 years together and moved to Utah.

"I started thinking maybe this isn't working for me," Christine told People in August. "And then I stopped believing in polygamy. I realized I didn't really want to live it anymore. I didn't like sharing a husband or feeling like I wasn't important."

Kody legally married first wife Meri Brown in 1990, after which sister wives Janelle Brown and Christine joined him in spiritual matrimony in 1993 and 1994, respectively. He and Meri divorced and fourth wife Robyn Brown became his legally recognized spouse in 2014. 

"I want a guy who actually loves me and wants to be with me intimately," Christine said. "I will be a monogamist from here on out."

Janelle has also since left the fold, Kody revealing in the December 2022 reunion special that they were separated.

Jeff Bezos and MacKenzie Scott

OK, so the couple that earn their first billion together don't necessarily stay together.

News of the Amazon founder and sometimes-richest-man-in-the-world's divorce from his wife of 25 years in January 2019 came as a shock—though mainly because Bezos was already involved with not-yet-divorced Good Day L.A. co-host Lauren Sanchez and the National Enquirer published their romantic text messages. (Bezos, who shares four children with Scott, countered that they were long-separated so the tabloid didn't have much of a scoop.) 

Scott, who married Seattle science teacher Dan Jewett in March 2021, received a reported $38.3 billion worth of Amazon stock in her divorce settlement, turning her into one of the world's richest people as well. She signed The Giving Pledge, a promise to give at least half of her fortune to charity, in 2019.

Jewett made the vow as well after their wedding, but Scott filed for divorce on Sept. 26, 2022.

Danny DeVito and Rhea Perlman

Married for 30 years, the Matilda co-stars announced in 2012 that they were separating—but the parents of three never pulled the trigger on a divorce.

"We're still separated, but we see each other often, and we're still a family," Perlman told People in August. "We can do things together, we can do things separately. I'm really, really glad that Danny and I were able to navigate some rough days to be able to have this different kind of relationship. I think it's pretty rare, but we agree on so many things that it makes sense."