Celebrities’ biggest heartbreaks

The love lives of celebrities are plastered all over magazines and entertainment television shows daily. There is rarely a hookup, marriage, breakup or divorce that we don’t know of (some before they even actually happen). However, despite the fact that we are pretty involved in our favorite celebrities’ love lives, more than we should be, there are breakups that none of us saw coming.


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We sometimes even forget that famous people are people too and their heart can be broken just like the hearts of the rest of us. And when this all happens in front of millions of people, it hurts much more.

This list contains the mother load – the breakups of the couples that we NEVER imagined could be possible. An element of our current digital world is that we seem to feel more and more connected to celebrities, almost as if they were our friends. That being said, it explains the way we react when we hear of a beloved couples decision to call it quits, and why our jaws usually drop and our hearts break a little for them.

While many of these couples have been in many relationships, the love mentioned here was IT for us.
From Jennifer Aniston and Brad Pitt (the classic case of a celebrity couple that divorced and traumatized us for life), Pamela Anderson and Tommy Lee (the couple that just couldn’t get enough of each other), to Blake Shelton and Miranda Lambert, and Steven Seagal and Kelly Le Brock; all of these couples were a glimpse into a true Hollywood fairy tale that we wished would be true.

Love is always the goal for many of us, and celebrities are no exception. Go ahead and go through the most epic loves of some of the most famous people to grace the big and small screen.

Angelina Jolie & Billy Bob Thornton

Angelina and Billy Bob were married from 2000 until 2003. The marriage may have been short but the entire relationship was one of the most PDA-filled relationships she has ever had and we think the ‘biggest’ one too (Brad Pitt including).

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Angelina Jolie & Billy Bob Thornton

Angelina and Billy Bob met on the set of the film Pushing Tin back in 1999. Each of them was in a relationship with another until they officially announced their relationship a few months later (while wearing vials of each others blood around their necks). On their divorce, Angelina said, “It took me by surprise, too, because overnight, we totally changed. I think one day we had just nothing in common. And it’s scary but… I think it can happen when you get involved and you don’t know yourself yet.”

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Pamela Anderson & Tommy Lee

Baywatch actress Pamela Anderson, has been in many high-profile relationships throughout her years in the spotlight. Her most famous relationship, and the most persisting one, was with Tommy Lee. The two were married from 1995-1998 and got back together again from 1999-2001 and AGAIN from 2008-2010. These two just can’t quit each other.

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Pamela Anderson & Tommy Lee

Pam and Tommy have two sons together, Brandon and Dylan. Pamela has been linked to Kid Rock and Rick Salomon but when it comes to her love life, Tommy seems to have been her one true love.

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Brad Pitt & Jennifer Aniston

Oh this one hurt probably more than most. Brad and Jennifer were the ‘it couple’ of the early 2000s with their beautiful blonde presence all over Hollywood. The two were married from 2000 until 2005; needless to say we all thought they would be together forever.

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Brad Pitt & Jennifer Aniston

In 2005 the couple announced their decision to file for divorce, stating, “it is not the result of any tabloid speculation” – sure it wasn’t. We all know Brad meeting Angelina Jolie during the filming of Mr. and Mrs. Smith probably had something to do with it, but that’s, well, pure speculation.

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Gwen Stefani & Gavin Rossdale

The No Doubt front woman and the Bush guitarist and lead singer were music’s power couple! Stefani and Rossdale met in 1995 and married in 2002 in two ceremonies (she wanted to wear her dress twice, naturally). They welcomed three sons into the world – Kingston, Zuma, and Apollo.

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Gwen Stefani & Gavin Rossdale

Shockingly for us all, Gwen and Gavin announced their plans to divorce in 2015, finalizing the proceedings in 2016. For the longest time we had no idea how to think of them as separated, but now that we see that it was for the better (Gwen is dating country singer Blake Shelton of all things) we are processing it better.

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Britney Spears & Justin Timberlake

Britney and Justin were the pop super couple that we all thought would make it down the aisle. The singing duo were together from 1999 until 2002 and made endless red carpet appearances together (remember that matching denim outfit they donned on the carpet?).

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Britney Spears & Justin Timberlake

Each of them went on to marry and have children (as well as a mental breakdown on behalf of Britney, but we are happy she made it out the other end of that and is now back on top). Justin is married to actress Jessica Biel, with whom he has a son with. While they moved on from each other, to us, they are the IT couple of pop forever.

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Bruce Willis & Demi Moore

Bruce and Demi – just their names rang a sweet bell for us. The two were a Hollywood power couple for much of the 90s, marrying in 1987 and welcoming three daughters together.

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Bruce Willis & Demi Moore

While the couple decided to end their marriage in 1998, due to the fact that they didn’t spend enough time together, the remained very close. So close in fact that when Demi remarried Ashton Kutcher, Bruce would join them on their vacations. Willis said, “It’s hard for people to understand, but we go on holidays together. We still raise our kids together – we still have that bond. Demi is the mother of my children.”

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Macaulay Culkin & Mila Kunis

Both Mila and Macaulay are child stars, which is essentially what made these two as bonded as they were. The two were in a serious relationship from 2002 until they broke up in 2010.

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Macaulay Culkin & Mila Kunis

While each of them moved on with other people, Mila with actor Ashton Kutcher whom she married and had two children with; and Macaulay going through some rough years and currently destabilizing, it seems like this love of theirs was a big one.

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Susan Sarandon & Tim Robbins

Susan Sarandon, known for her role in films like The Witches of Eastwick, Little Women, and Stepmom spent the better part of the 90s and 2000s with fellow actor Tim Robbins. More specifically, the two were together from 1988 until 2009.

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Susan Sarandon & Tim Robbins

Susan and Tim have two sons together, in addition to Susan’s daughter from a previous relationship. Sarandon is now very active in her political stances and Tim is busy with his own acting career.

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Ben Affleck & Jennifer Garner

The divorce heard round the world. Jennifer and Ben are not technically divorced yet but they are well on their way. The couple, who married in 2005, have three children together and have been fighting to save their marriage after Ben’s infidelity.

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Ben Affleck & Jennifer Garner

Today, the two are raising their children together as Ben still lives in the family’s property (in the guest house, though), making them the number one priority, as it should be.

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Sandra Bullock & Jesse James

Not going to lie, this breakup made us very mad. The beautiful and kind actress Sandra Bullock married what seemed to be her complete opposite in the best way possible – Jesse James – in 2005. The two were married for five years before infidelity allegations were circulating.

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Sandra Bullock & Jesse James

After their 2010 divorce, things got better for Sandra. She adopted two children over the course of the following five years and had been linked to Bryan Randall, a photographer, since 2015.

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Helena Bonham Carter & Tim Burton

Helena and Tim were a creator and muse situation from the very beginning. They met in 2001 on the set of their mutual film Planet of the Apes, and instantly hit it off. They were together in a domestic partnership for 13 years and had two children together.

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Helena Bonham Carter & Tim Burton

During the time they were together, Burton had Helena appear in almost all of his films (we did say she was his muse, right?). On her relationship with Burton, Carter said, “Sometimes you’re not meant to be forever together. But that was a gift, a massive gift. We gave each other children and a lot more.”

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Reese Witherspoon & Ryan Phillippe

Reese and Ryan married when she was just 23 years old, which is what Reese credits as the reason for the marriage’s failure, stating, “I was ridiculously young”. The couple was married from 1999 through 2006.

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Reese Witherspoon & Ryan Phillippe

Reese and Ryan share two children together, daughter Ava and son Deacon. Reese said, “I learnt a lot, though. It was an excellent opportunity for me to really find out what it means to be a partner and to be in a marriage and it’s not anything that I thought it was.”

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Bruce Jenner & Kris Jenner

Former Olympic gold medal winner Bruce Jenner and former wife Kris Jenner were married from 1991 until 2015. The two had two children together in addition to other children from each of their previous marriages.

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Bruce Jenner & Kris Jenner

In 2015, Bruce came out as transgender and transitioned from male to female, changing his name to Caitlyn Jenner. The entire dramatic change can be seen on the E! entertainment channel reality show Keeping Up with the Kardashian, as well as Caitlyn’s own reality show.

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Gwyneth Paltrow & Chris Martin

Actress Gwyneth Paltrow and Coldplay frontman Chris Martin were a match made in Hollywood heaven. The beautiful couple married in 2003 and managed to keep their personal life private (quite the accomplishment)! They have two children together, daughter Apple and son Moses.

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Gwyneth Paltrow & Chris Martin

In 2016, though, the couple divorced and ended what we all thought would be a marriage for the ages. The two remain very close, which is such a mature way to go (especially for the kids) and we wish them nothing but continued respect and success.

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Jennie Garth & Peter Facinelli

Former 90210 starlet Jennie Garth, married actor Peter Facinelli in 2001. He was her second marriage but her greatest too. Jennie and Peter were married from 2001 until 2013, when they stunned fans by announcing their divorce after so many years and three children together.

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Jennie Garth & Peter Facinelli

Jennie went on to remarry in 2015 and Peter was engaged to another actress for a while before calling that off as well. Whatever the case may be, we LOVE these two together and know that they were it for each other.

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Robin Wright & Sean Penn

The Princess Bride herself married Sean Penn in 1996, her second marriage and last marriage as of yet. Wright and Penn were married from 1996 until 2010, welcoming two children during their marriage.

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Robin Wright & Sean Penn

When the couple filed for divorce in 2010 we were incredibly surprised since they managed to overcome all of the other obstacles that their relationship threw at them (they separated twice during their marriage). Wright went on to be engaged again to actor Ben Foster but later broke off her engagement. Penn has been linked to actress Charlize Theron but that also seems to have fizzled out.

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Jennifer Lopez & Marc Anthony

Jennifer and Marc were THE music couple when they were together. The longtime friends married in 2004, much to the joy of their fans. They welcomed twins Max and Emme in 2008.

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Jennifer Lopez & Marc Anthony

The couple announced that they were separating back in 2011, breaking our hearts and shocking us to the core. They officially divorced in 2014 after 10 years of marriage. The statement given at the time was: “We have decided to end our marriage. This was a very difficult decision. We have come to an amicable conclusion on all matters. It is a painful time for all involved and we appreciate the respect of our privacy at this time.”

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Leonardo DiCaprio & Gisele Bundchen

We all know that Leo has a thing for blonde models. He has had a long list of famous girlfriends but Gisele was (so far) the BIG one, at least in the eyes of his fans. The couple was together from 2000 until 2005. Honestly, most people thought that Gisele was going to be the one to tame the playboy actor; sadly, that wasn’t the case.

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Leonardo DiCaprio & Gisele Bundchen

When Gisele got tired of waiting to get proposed to, she broke up with Leo. These days, Gisele is married to the New England Patriot’s quarterback Tom Brady and has two children with him. Leo, is, well, still dating young blonde models.

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Miranda Lambert & Blake Shelton

Country music fans everywhere were in a frenzy when they learned that Miranda and Blake were getting married after four years together back in 2010. The couple was married until 2015 when they announced their divorce the same day that it was finalized.

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Miranda Lambert & Blake Shelton

The couple came out with a statement that broke our hearts with its honesty, stating, “This is not the future we envisioned and it is with heavy heart that we move forward separately. We are real people, with real lives, with real family, friends and colleagues. Therefore, we kindly ask for privacy and compassion concerning this very personal matter.” Each has moved on to date new people, Blake is now linked to singer Gwen Stefani.

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Melanie Griffith & Antonio Banderas

Melanie and Antonio had one of the most passion-filled relationships the red carpet ever had the audacity to see. While Melanie was married twice before, this relationship seemed to be it. The couple has one daughter together (in addition to Melanie’s two older children from her two previous marriages).

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Melanie Griffith & Antonio Banderas

Sadly, Mel and Antonio didn’t last and after almost 20 years of marriage they announced their divorce in 2015. Needless to say we were very saddened by the news of their breakup.

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David Arquette & Courteney Cox

The Scream co-stars and adorable duo, David Arquette and Courteney Cox, married in 1999 during Cox’s long stint as Monica Geller on Friends. The couple has one daughter together, Coco.

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David Arquette & Courteney Cox

In 2010, the couple announced their trial separation, followed by their 2012 official divorce from each other. Courteney stated, “When you love someone, you want them to be happy, even if it’s not with you, we were married for a long time, so it’s not like we didn’t try.”

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Jon Hamm & Jennifer Westfeldt

Mad Men’s Jon Hamm and actress Jennifer Westfeldt were in a longstanding relationship from 1997 until their SUPER sad breakup in 2015. The couple talked openly about the fact that they were not planning on having children together (red flag?).

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Jon Hamm & Jennifer Westfeldt

When the two announced their breakup we would be lying if we said we weren’t upset about it. The boyfriend and girlfriend duo really had us believing they were going to be the ones who made it through this crazy world together.

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Joshua Jackson & Diane Kruger

Dawson’s Creek actor Joshua Jackson was in a longstanding relationship with German beauty and actress Diane Kruger from 2006 until the end of 2016. The couple never married but didn’t seem to need the validation – no one saw their breakup coming. The two shared three homes together across the globe.

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Joshua Jackson & Diane Kruger

While they are no longer together, the couple is still close and most recently Joshua congratulated Diane on winning the best actress award at the Cannes Film Festival. They were without a doubt one of our favorite couples and are clearly mature enough to remain friends.

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Johnny Depp & Vanessa Paradis

Pirates of the Caribbean star Johnny Depp, met French model Vanessa Paradis in 1998 and made the world fall in love with them. Johnny and Vanessa never married but had two children together, Lily Rose and John Christopher III.

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Johnny Depp & Vanessa Paradis

The stunning duo remained in a committed relationship until 2012, at which time they announced their mutual decision to end their relationship. Depp went on to marry actress Amber Heard, which we all know ended very badly for him. Vanessa was at Depp’s side when the abuse allegations were brought forth.

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Elizabeth Taylor & Richard Burton

Elizabeth was known for many things, one of which were her many marriages. Two of those marriages, however, were to the same person – Richard Burton. The actors were married from 1964-1974 and once again from 1975-1976.

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Elizabeth Taylor & Richard Burton

While they loved each other very much, the two were said to have had a little too much passion in their relationship – both the good kind and the bad – causing friction. The reason for their divorce, according to Taylor, was: “maybe we loved each other too much”. Is there such a thing?

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Tom Cruise & Nicole Kidman

We could tell you the demise of this union – Tom’s religion (Scientology). However, Nicole would say the reason had more to do with her being very young when they were married. Nicole was 23 years old when she married Tom in 1990. The couple adopted two children together.

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Tom Cruise & Nicole Kidman

In 2001, the couple announced their separation. Kidman stated after the fact that, “I was a child, really, when I got married. And I needed to grow up.” Kidman is now married to country singer Keith Urban and has two children with him. Cruise married actress Katie Holmes and had a daughter with her but subsequently divorced.

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Madonna & Guy Ritchie

op queen Madonna married film director Guy Ritchie in 2000. The couple was an unlikely pair from the get go but it seemed to work for a while. They welcomed son Rocco and later adopted son David Banda from Malawi together.

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Madonna & Guy Ritchie

In 2008, they announced their intentions to divorce. Madonna said, “When you start off, everything’s great and lovely, and the person you’ve married is flawless, and you’re flawless, then time goes by, and you share a life, you have children, and there are cracks in the veneer. It’s not as romantic as it used to be. You think, ‘This isn’t what I thought it was going to be,’ and ‘How much am I willing to sacrifice?'”

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Dennis Quaid & Meg Ryan

Dennis and Meg were married in 1991. The two had a lot of ups and downs in their relationship due to Dennis’ substance abuse issues, which Ryan made him face before the two were to marry.

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Dennis Quaid & Meg Ryan

The couple had one son together, Jack. They divorced in 2001. Dennis went on to remarry in 2004 and have two more children. Meg adopted a daughter from China in 2006 and went on to have a longstanding relationship with singer-songwriter John Mellencamp.

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Heidi Klum & Seal

Heidi and Seal renewed their vows every single year after they got married in 2005, which is the sweetest thing. The couple has four children together, one of which Seal adopted as his own after marrying Heidi.

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Heidi Klum & Seal

We NEVER thought these two would call it quits, truly. The couple, who was married in 2005, separated in 2012 and officially divorced in 2015. The official reason for the divorce, according to Heidi was: “we have grown apart”. The duo was fond of throwing elaborate Halloween parties and overshare their love for one another with public displays of affection. We miss them!

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Steven Seagal & Kelly Le Brock

Steven Seagal, iconic Hollywood actor, has been married a total of four times throughout his life. It was his third marriage to Kelly Le Brock that we are focusing on here as it was his highest profile relationship and his most volatile. Steven and Kelly were married from 1987 until 1996. The couple got together while Steven was still married to second wife Adrienne La Russa.

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Steven Seagal & Kelly Le Brock

Steven and Kelly have three children together, in addition to his two older children from his first wife, Miyako Fujitani. After his divorce from Kelly, Steven went on to marry one last time and have another child. Steven has a total of seven children (he had another one with the nanny who was taking care of his children with Kelly). While it all sounds very dramatic, and it was, his love for Kelly was the ultimate he has had.

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Sylvester Stallone & Brigitte Nielsen

Sylvester Stallone, famous for his role as boxer Rocky Balboa, was married to actress and model Brigitte Nielsen from 1985 until 1987. Their marriage was short lived but their relationship was so high-profile that it was impossible to ignore.

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Sylvester Stallone & Brigitte Nielsen

Stallone remarried after his divorce from Nielsen to his now-wife of 20 years Jennifer Flavin. Stallone has five children, two from his first marriage to Sasha Czack and three from his last marriage to Jennifer Flavin.

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