30 Of The Most Surprising And Devastating Celebrity Breakups Of All Time

Celebrity breakups are often just as dramatic and surprising as regular breakups, and it's not a surprise that many of us are wrecked after our favorite famous faces call it quits. Throughout the years, there have been some truly surprising and downright startling celebrity breakups.

From Sonny and Cher to Brad and Jen to Brad and … well, quite a lot of people, actually, here are 30 of the most surprising and devastating breakups of all time. If there's anything to learn from these stories, it's that celebrities truly are just like the rest of us, for better or for worse.

Will Arnett and Amy Poehler

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Will Arnett and Amy Poehler got married in 2003 and have two children together: Archie and Abel. People really loved seeing these two comedians together and were devastated when they announced their separation in 2012.

While speaking to Dax Shepard on his podcast, Armchair Expert, Will explained that the public reaction to their divorce made it even harder: "We're human beings in a relationship, and our relationship fell apart. It's really sad. It's heartbreaking. We have two kids, and this is not some [expletive] game. What are you talking about? You have no [expletive] clue what our experience is."

Jennifer Aniston and Brad Pitt

Jennifer Aniston and Brad Pitt went on their first date in 1998 and made things official at the Emmy Awards in 1999. Fast-forward to November 1999 and they were engaged, and then they held a huge wedding in 2000. Things seemed great until all of a sudden they weren't; in May 2004 Brad Pitt met Angelina Jolie on the set of Mr. & Mrs. Smith, and Jen and Brad announced their separation in January 2005.

Elvis and Priscilla Presley

Elvis and Priscilla Presley were seen as an it couple long before it couples were a thing. The pair met in 1959, when Priscilla was a teenager and Elvis was stationed on the same base in Germany as her father. The singer moved Priscilla in with him in the years that followed, and the two got married in 1967.

Elvis and Priscilla welcomed their daughter, Lisa Marie, nine months later. They divorced in 1973 but remained close friends until Elvis' death in 1977.

Angelina Jolie and Brad Pitt

Angelina and Brad met on the set of Mr. & Mrs. Smith in 2004 and were spotted on vacation together in Kenya the following year. In January 2006, the pair shared they were expecting their first biological child together, and Brad adopted Angelina's children Maddox and Zahara. Their son Pax joined the family in March 2007, and in May 2008 the pair revealed they were expecting twins Knox and Vivienne.

Angelina and Brad got engaged in 2012 after years of media speculation and finally tied the knot in April 2014. For a while, it seemed like everything was perfect. Angelina caught many by surprise when she filed for divorce in 2016, with her lawyer only specifying, "This decision was made for the health of the family. She will not be commenting, and asks that the family be given its privacy at this time."

Arthur Miller and Marilyn Monroe

Marilyn Monroe's longest marriage was to the third man she married, Arthur Miller. The two met in 1950 but didn't enter into any kind of relationship right away. They began exchanging letters and reconnected in 1955. Arthur Miller filed for divorce from his wife in 1956, and the pair married in the same year.

Marilyn attempted to get pregnant several times the following year, but suffered two miscarriages and an ectopic pregnancy loss. The pair ended their marriage four years after it began, and Arthur declined to attend her funeral in 1962.

Bridget Moynahan and Tom Brady

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Bridget Moynahan and Tom Brady were together for about three years before breaking up in 2006. Tom began dating Gisele Bündchen that same year, but two months into that relationship he received some unexpected news: Bridget was pregnant with his baby.

Bridget told Harper's Bazaar that being a single mom wasn't her plan: "When you're suddenly pregnant and no one is standing by your side, even if you're in your 30s, it's a hard conversation. I'm a traditional girl, and I believe in marriage, and I just always thought that's the way I'd be doing this. For a moment, it was hard for me to accept that this was the way I was going to have a family."

Gisele supported Tom throughout Bridget's pregnancy, and spoke well of Bridget and Tom's son. While none of the adults involved have spoken directly about their co-parenting arrangement, in 2011 Bridget said, "I have a relationship with these people on a daily basis. I'm raising a child, and it's public. My son has two loving parents and an extended family, whether it's cousins or stepmothers or boyfriends. My son is surrounded by love."

Charles, Prince of Wales, and Diana, Princess of Wales

Most of us know the story of Prince Charles and Princess Diana, but that doesn't make the details of their relationship, marriage, and divorce any less compelling. The pair met in the 1970s when Charles was dating Diana's sister, but they really connected in 1980. They became engaged the following year and were married in July 1981.

They celebrated the births of their sons, Prince William and Prince Harry, in 1982 and 1984. By 1986, both were having affairs. That year, Charles wrote in a letter, "How awful incompatibility is, and how dreadfully destructive it can be for the players in this extraordinary drama. It has all the ingredients of a Greek tragedy … I never thought it would end up like this."

The pair held on until 1992, when they finally announced their intention to divorce. It took several years for the deal to be official, but the palace announced their divorce was finalized in August 1996.

Christie Brinkley and Peter Cook

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Christie Brinkley and Peter Cook were married from 1996 to 2008, which is definitely a respectable amount of time. Peter adopted Christie's son, Jack, and the two share a daughter named Sailor.

The two reportedly divorced after Peter Cook was caught in an affair with his then 19-year-old assistant.

Elin Nordegren and Tiger Woods

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Elin Nordegren married golfer Tiger Woods in October 2004 after being introduced by Elin's former employer at a golf tournament in 2001. They have two children together, Sam and Charlie. The two weathered multiple rumors that Tiger was cheating on Elin, and everything came crashing down around them in 2009. Elin filed for divorce in 2010.

Elizabeth Taylor and Richard Burton

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Richard Burton and Elizabeth Taylor met in 1962 on the set of Cleopatra. Elizabeth told People that though the pair had met before making the movie, working together on set is what brought them together. "When I saw him on the set of Cleopatra, I fell in love and I have loved him ever since."

Their relationship was known for being volatile, and they were both in relationships with other people when they met. Eventually they both divorced, and they got married in March 1964. They made 11 movies together, and even with all the drama surrounding their marriage, the public loved them.

They divorced in 1974 but remarried in October 1975. The second marriage ended less than a year after it began.

Reese Witherspoon and Ryan Phillippe

Reese Witherspoon and Ryan Phillippe's relationship was definitely like something out of a late 1990s/early 2000s romantic comedy, which is pretty appropriate given their careers. They were introduced at Reese's 21st birthday party, and they were engaged a year later. Reese got pregnant with daughter Ava before the wedding, and they got married three months after the debut of their film together, Cruel Intentions.

Reese and Ryan seemed to go strong for quite some time. Reese gave birth to their son, Deacon, four years after they got married.

Everyone was surprised when they divorced in 2007, but in 2015, Ryan explained to Larry King why it went wrong: "I think more of the problem was age. When we got together we were so young. I think it can create issues with two people in this industry because there's so much noise that goes along with it."

Britney Spears and Justin Timberlake

Britney and Justin first met in 1992, when they both starred on The All-New Mickey Mouse Club. They reconnected after both launched successful pop careers, and they were in a full-blown relationship in 1999. People were stunned when they broke up in 2002. In the years that have followed, details about the reality of their relationship have been provided in the media and in documentaries.

Nick Lachey and Jessica Simpson

Jessica Simpson and Nick Lachey were another big couple from the early 2000s. They were introduced in 1998 but didn't hit it off until 2000. They broke up briefly in 2001 before getting back together and then got engaged in February 2002. Following their wedding, they launched a reality show called Newlyweds on MTV.

However, their bliss didn't last. The couple announced their intention to divorce in November 2005. Nick later said he was told the marriage was ending, but he wouldn't have chosen that reality. He told Rolling Stone, "I never wanted to be a divorcé. I wanted us to be happy. I guess we differed on strategy."

Ben Stiller and Christine Taylor

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Christine Taylor and Ben Stiller got married in 2000 and proceeded to work together on numerous occasions. Over the years, they projected an image of a wholesome, happy family to the world, which made their 2017 announcement that they planned to separate all the more confusing.

To make things even more bewildering, they began attending events together in 2019.

Ellen DeGeneres and Anne Heche

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Ellen and Anne met at the Oscars in 1997. Ellen explained, "And then I met her at the Vanity Fair party. And it was a chemistry thing that you can't really describe. It just happened. Obviously I was attracted to her, but that wasn't enough. There are a lot of attractive people. She is so unique."

The pair were going strong for over three years when Anne allegedly just left their home one day and never came back.

Frank Sinatra and Mia Farrow

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Mia Farrow married Frank Sinatra when she was only 21 years old and reportedly lost her virginity to him. While the pair were enamored from the beginning of their relationship, after they got married it seems problems began pretty quickly.

The pair ended up divorcing in 1968 because Frank wanted Mia to quit acting and focus on being his wife.

Heidi Klum and Seal

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Heidi Klum and Seal began dating in 2004. They got married in May 2005, welcoming son Henry in the same year. Two more children — Johan and Lou — quickly followed. Seal adopted Heidi's daughter Leni from a previous relationship.

The pair announced their intention to divorce in 2012 and released a simple statement by way of explanation: "While we have enjoyed seven very loving, loyal, and happy years of marriage, after much soul-searching we have decided to separate."

Jennifer Lopez and Ben Affleck

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It's hard to believe it given how much attention they got, but Ben Affleck and Jennifer Lopez were together for only two years. They met in 2002 on the set of Gigli and got engaged quickly, but they postponed their wedding due to all the media attention they received. The pair ended their engagement for sure in 2004.

Mariah Carey and Nick Cannon

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Mariah Carey and Nick Cannon got married in 2008 after dating for six weeks, which surprised just about everyone on the planet. But they seemed to make it work and were married for three years before welcoming their twins.

When they announced their separation in 2014, they made it clear their kids were the most important part of their union. In 2017, Nick explained, "You put the kids first, but then when you understand that you have unconditional love for these human beings and you want the best existence for them, then you put whatever differences you may have had aside."

Sarah Jessica Parker and Robert Downey Jr.

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Sarah Jessica Parker has been married to husband Matthew Broderick for so long that it might be hard to remember that she once dated Robert Downey Jr., along with a few other famous faces. Sarah met Robert in 1984, when they both appeared in the film Firstborn. They quickly moved in together and even began joking about wedding plans in the media.

However, Robert was struggling with his now infamous addiction woes, and after seven years, Sarah Jessica ended things. She told People that she spent a lot of time taking care of him: "There was a huge amount of time spent making sure he was okay. At a certain point, I had the courage to say, 'I'm going to walk away and I'm just going to pray that you don't die.' I will say, I don't regret any of it. I don't resent the time spent."

Gwyneth Paltrow and Brad Pitt

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Gwyneth Paltrow and Brad Pitt began dating in 1994, and Brad proposed two years later. Neither party has spoken ill of the other since they broke up, and Brad moved on to date Jennifer Aniston not long after. Gwyneth did tell Howard Stern that she thinks she was simply too young to be with Brad:

"I was such a kid. I mean I was 22 when we met and it's taken me until 40 to get my head out of my [expletive]. You can't make a decision when you're 22 years old … I think I was a kid and I wasn't ready, and he was too good for me."

Cher and Sonny Bono

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Sonny and Cher were the iconic couple of their era. Their relationship would certainly raise quite a few eyebrows these days, as Cher was only 16 when she met 27-year-old Sonny Bono. He was separated from his first wife at the time, and Cher even moved in with Sonny before the two ever pursued a romantic relationship.

In 1975, Cher explained that their relationship was about being safe: "It wasn't a fiery, sexy thing with us, but rather paternal, like we were bound together, two people who needed each other, almost for protection."

Their relationship and careers intertwined, and when the pair married in 1969 they were famous around the world. By the time they were both ready to divorce, it was difficult to extricate themselves from the career they had built together. Their divorce ultimately finalized in 1975.

Justin Bieber and Selena Gomez

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Selena Gomez and Justin Bieber are kind of like the Britney Spears and Justin Timberlake of their day. The pair became official in 2011 but were soon dogged by cheating rumors when Justin was accused of fathering a baby with a fan later that year (paternity tests cleared him). They broke up in 2012 but continued to see each other off and on, and even appeared to reconcile in 2013.

Ben Affleck and Jennifer Garner

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Jennifer Garner first met Ben Affleck on the set of Pearl Harbor in 2000, and they began dating in 2004. They married pretty quickly thereafter in 2005, and they have three children together.

The two seemed to have a strong marriage for years, but things began to unravel when Ben reportedly began a relationship with the family's nanny in 2015. However, Jennifer later told Vanity Fair that the nanny wasn't the reason they split up: "We had been separated for months before I ever heard about the nanny. She had nothing to do with our decision to divorce. She was not a part of the equation. Bad judgment? Yes."

Jennifer and Ben announced their decision to divorce in 2017.

Gwyneth Paltrow and Chris Martin

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Gwyneth Paltrow and Chris Martin were together for 11 years and have two kids: Apple and Moses. For a long time, they seemed like the couple who had everything figured out. After meeting in 2002 backstage at a Coldplay concert, the two began spending a lot of time together, and they got married the following year.

The pair surprised everyone with their decision to separate in 2014.

Kourtney Kardashian and Scott Disick

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Kourtney and Scott met back in 2006, and the pair were an immediate focus of Keeping Up With the Kardashians when it debuted the following year. The two were on and off for years, and Kourtney gave birth to their first child together in December 2009.

They famously never married but went on to have two more children together. The pair finally ended things for good in 2015 and haven't looked back.

Kim Kardashian and Kanye West

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Kim and Kanye met back in 2003 after being introduced by Brandy, and Kanye was open about almost immediately having a crush on her. They reconnected in 2008, and Kanye appeared on the family's reality show in 2010. The two went official in 2012 and announced they were expecting a baby in the same year.

In the years that followed, the pair welcomed four children. Kanye proposed to Kim in 2013, and they got married in May 2014.

Kim filed for divorce from Kanye in February 2021.

Bruce Willis and Demi Moore

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Bruce Willis and Demi Moore met at a film premiere in 1987 and got married in the same year. The pair welcomed three children between 1988 and 1994, while both were in successful periods in their careers.

People were stunned when they separated in 1998, but since then the two have become excellent co-parents.

Desi Arnaz and Lucille Ball

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Lucy and Desi got married six months after they first met, but they defied the odds and stayed married for 20 years. The decision to work together on I Love Lucy was made in part because the couple hoped it would help keep their marriage together.

However, Lucille Ball ended up filing for divorce in 1960 and went on to buy out Desi's stake in their production company, Desilu.

Debbie Reynolds and Eddie Fisher

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Debbie Reynolds and Eddie Fisher were both successful when they met and married in 1955. The pair welcomed their daughter, Carrie, in 1956, and continued to each work in the entertainment industry. The pair were good friends with Elizabeth Taylor and her husband at the time, Mike Todd, and even named their son Todd after their good friend.

Eddie Fisher went to comfort Elizabeth Taylor after her husband died, and eventually the two fell into a relationship. Eventually, Debbie agreed to divorce her husband, and he married Elizabeth.