19 Nastiest Celebrity Couple Break Ups

A great poet named Alfred Tennyson, once wrote, “Tis better to have loved and lost/Than to have never loved at all.” An awesome band, Nazareth, once sang, “Love hurts, Ooo-oo, love hurts.” At one point in life, most people go through a horrible and painful break up. They stay up late at night, softly sobbing to themselves, holding a cherished token and wondering, “Why God? Why? My heart hurts so much.” Well, it happens and it is very unpleasant. The only way to mend a broken heart is to be sad, listen to lots of Adele, watch The Princess Bride and move on. Sometimes a break up can be a mutual decision, but other times it can be a nasty, bloody, pier six brawl. There isn’t just crying but also fighting, swearing and really loud yelling. It’s not easy for anyone, but at least a regular person doesn't have to worry about their heartbreak trending on Twitter.

Some of the most famous celebrity couples have had very public, nasty and ruthless break ups. Celebrity couples are just like normal couples, everything starts out amazing. It’s like skipping in a meadow, with birds chirping and flowers blooming. Sometimes, like a normal couple, they skip right into a dark swamp. Sometimes things just don’t workout. However, a celebrity couple’s break up often becomes a hot topic. Some couples split on very bad terms and the break up is brutal. Here is a look at 19 of the nastiest celebrity couple break ups.

19 Justin Timberlake and Britney Spears

In 1999, Pop Icons Britney Spears and Justin Timberlake began dating. Suddenly, things ended in March 2003 and speculation arose over what led to the break up. Apparently, the break up helped inspire Timberlake’s first solo single, “Cry Me A River”. The video was controversial, as it depicts a Britney look-a-like that cheats on Justin. He gets his revenge by making a sex tape in the Britney look-a-like’s bed. Britney was devastated over the song and video, the real Britney not the look-a-like. Rumors suggest that the song, “Everytime”, is in response to “Cry Me A River”. Both have moved on with their lives.

18 Hulk Hogan and Linda Hogan


WWE legend, Hulk Hogan married Linda Claridge, in 1983. The entire Hogan family was featured in the reality series, Hogan Knows Best. They have two kids together, Brooke and Nick Hogan. Allegations were made that Hulk had an affair with one of Brooke’s friends, who was helping with her album at the time. Linda filed for divorce on November 20, 2007, and it came as a huge shock to the Hulkster. Hulk found out about the divorce when a reporter called to get his comment. The divorce was bitter and brutal. Hulk was left with 30% of their liquid assets and claims that he went through an intense suicidal depression. She got $7.4 million, several cars, several houses and the World Wrestling Heavyweight Title. Okay, she didn’t get the world title but she ended up dating Charlie Hill. She was 48 and he 19 at the time; in fact, he went to school with her kids. Not to be outdone, Hogan is now married to Jennifer McDaniel, 21 years his junior.

17 Seal and Heidi Klum


Musician Seal, and Supermodel Heidi Klum, were married on May 10, 2005, on a beach in Mexico. Their love was so deep and strong, that they would renew their wedding vows each year on their anniversary. So, it was a huge shock to everyone when, in 2012, they announced they were separating. Reportedly, a part of the reason that the 7-year marriage ended was partially because of Seal’s bad temper. Before officially divorcing, Heidi began a relationship with her bodyguard. This made Seal irate, who regretfully stated that he hoped Heidi would have waited for the divorce to be finalized before, “fornicating with the help.”

16 Nicole Kidman and Tom Cruise

15 Halle Berry and Gabriel Aubry

Hollywood actress, Halle Berry and model Gabriel Aubry began dating in 2006. They had a daughter, Nahla together, born in 2008. The couple broke up in 2010. They had an agreement in place concerning the raising and custody of their daughter. However, things got seriously nasty when Berry started a relationship with Olivier Martinez and tried to move with her daughter to her new husband’s home in France. This violated the terms of the agreement and a judge ruled in favor of Gabriel, blocking Halle for moving with her daughter. They had a highly publicized custody battle that resulted in Oliver and Gabriel having a fistfight, which resulted in both suffering injuries requiring medical attention.

14 Pamela Anderson and Tommy Lee


Actress/Playboy Playmate, Pamela Anderson married Motley Crue drummer, Tommy Lee, on February 19, 1995. They married after knowing each other for 96 hours. They married on a beach and Pamela wore a bikini for the event. They have two sons together. It was a highly publicized relationship and became even bigger when a sex tape of the two was released. The relationship was often intense and violent. Tommy spent 180 days in prison on charges of spousal abuse. They divorced in 1998, but reconciled in 2001 and broke up again. In 2002, Pamela found out she had Hepatitis C and claimed she got it from Tommy Lee. Although, his representatives denied this claim and stated the allegations were false. They got back together in 2008, and split once more.

13 Sean Penn and Madonna


The relationship between the Pop Icon, Madonna and Hollywood Star Sean Penn, was reportedly intense, violent and nasty. They married in 1985 and right from the start, things were rough. By this point in his life, Sean Penn hated being in the spotlight. His marriage to Madonna attracted an intense amount of media coverage and it drove Penn crazy. At their wedding, he reportedly shot at helicopters hovering above and later attacked paparazzi. Eventually, Madonna wanted to separate and end the marriage. Reportedly, in 1987, Sean Penn, who was heavily intoxicated, climbed up the side of Madonna’s house and broke in while she slept. Apparently, he tied her to a chair and beat her for nine hours. They divorced but according to sources in later years, they became very good friends.

12 Alec Baldwin and Kim Basinger

11 Robert Pattinson and Kristen Stewart


Many people may not be aware but, vampires having feelings, too. Robert Pattinson and Kristen Stewart met on the set of the hit film series, Twilight, in 2008. They tried their absolute best to keep the relationship secret, but that’s impossible when you’re Edward and Bella. Fans and media speculation was intense and many wondered what was going on between them. In 2012, photos surfaced of Stewart being affectionate with a werewolf…er…sorry…director Rupert Sanders. That's when Robert and Kristen both acknowledged that they were together. However, they split shorty after the drama unfolded. He was even seen leaving her house with many of his personal items in 2013. Stewart apologized for deeply hurting Robert. However, both have now moved on.

10 Britney Spears and Kevin Federline

Pop Icon, Britney Spears married Kevin Federline, a.k.a K-Fed, on September 18, 2004. They have two sons together. Britney filled for divorce on November 7, 2006, citing irreconcilable differences. They divorced and reached an agreement. Everything seemed fine then suddenly; she attempted to get sole physical and legal custody of her kids. It became a very public and nasty feud. Also, during this time, Britney had many ups and downs that contributed to a very stressful life. In 2007, K-Fed was granted sole physical custody of the kids, with legal custody to be determined. In early 2008, Britney locked herself in a room with her son and refused to give her kids to K-Fed. She was taken to the hospital and appeared to be under the influence of a substance. Due to this incident, K-Fed was granted sole physical and legal custody. Britney received visitation rights that increased over time. She also has to pay $20,000 in child support.

9 Mariah Carey and Nick Cannon


Singer/songwriter Mariah Carey married rapper, comedian, actor and host Nick Cannon, in the Bahamas on April 30, 2008. They had twins born on April 30th, 2011. They would often renew their wedding vows in a lavish manner. In August of 2014, the news broke that Mariah and Nick had been separated. Shortly after, Nick confirmed the report, which apparently angered Mariah. They are now separated and both are seeking full custody of their twins. Nick has made claims that she is unfit to be a mother and is emotionally unstable. He claims that she lets the nannies raise the twins, while she spends all day analyzing pictures of herself, obsessing over her age and drinking champagne. On the other hand, Mariah has made claims that he lives a wild party lifestyle, has an extremely busy work schedule and has cheated on her. Both deny the allegations that have been made.

8 LeAnn Rimes and Dean Sheremet

Country singer LeAnn Rimes, married back up dancer Dean Sheremet, in 2002. During the marriage, she had an affair with actor Eddie Cibrian, who was cheating on his wife Brandi Glanville. Rimes and Sheremet separated in 2009 and Eddie also divorced Brandi. Eddie and LeAnn married on April 22, 2011. That’s when the ruthless, cruel and mean spirited, trash talking kicked into high gear. Specifically, Eddie, LeAnn and Brandi have engaged in a war of words. The affair and divorces have overshadowed any success the people involved have had, especially LeAnn. Brandi was able to turn the nastiest into a lucrative book deal and landed a role on Real Housewives of Beverly Hills.

7 Ashton Kutcher and Demi Moore


6 Sandra Bullock and Jesse James

Academy Award winning actress, Sandra Bullock married motorcycle builder and host of Monster Garage, Jesse James, on July 16, 2005. In 2010, she won the Oscar for Best Actress for her role in The Blind Side. The couple was in the process of adopting a child. In March, she truly got blindsided when it was discovered that James had affairs with several women. He apologized publicly and entered into rehab in order to save his marriage. It didn’t matter by that point, as Sandra wanted a divorce, which she got by June that year. Reportedly, she was crushed and devastated over the divorce but has moved on. She adopted the child as a single parent.

5 Denise Richards and Charlie Sheen

Many people have heard of Beauty and The Beast. Denise Richards and Charlie Sheen can probably be described as, Beauty and The Goon. Don’t worry though; Charlie would probably take that as a compliment. Denise Richards and Charlie Sheen married on June 15, 2002. They have two daughters together. The relationship was an intense one, especially for Richards. Sheen was addicted to drugs, alcohol and women. Richards filed for divorce on April 19, 2006. She claims that Sheen made “violent threats” towards her. However, time as healed many wounds for the two. They are now on better terms and even consider each other to be very good friends. Denise Richards was even awarded custody of Bob and Max, Sheen’s twin sons from his marriage with Brooke Mueller; while she dealt with her own drug addiction issues.

4 Kim Kardashian and Kris Humphries


It’s the typical love story: boy meets girl, boy falls in love with girl, boy marries girl…on hit reality show and then boy and girl stay together forever…er…72 days. Reality TV star Kim Kardashian married NBA star Kris Humphries on August 20, 2011. The preparations and wedding were broadcast as part of a two-part television special event. After 72 days of marriage, Kim filed for divorce. Kris Humphries in response, wanted an annulment, claiming that Kim just wanted to get married for ratings. Many in the media speculated that the marriage was all a publicity stunt, however Kim denies this. Surprisingly, the divorce proceedings took longer then 72 days, because Kris would not give into Kim’s demands. However, eventually they settled and divorced.

3 Tiger Woods and Elin Nordegren


Professional golfer, Tiger Woods married former Swedish model Elin Nordegren, on October 5, 2004. For a time, Tiger had it all. He was the highest paid athlete, was considered one of the greatest golfers of all time, had a plethora of endorsement deals and was married to an incredibly gorgeous woman. However, everything fell apart when it was revealed that Tiger had several affairs. Fifteen women came forward revealing their affair with the golfer. Tiger himself has admitted to sleeping with 120 women. Reportedly, Elin chased Tiger out of the house with a golf club when she found out the truth. He apologized to his wife and entered therapy for sex addiction. They divorced on August 23, 2010. Elin bought a mansion for $12 million with the money she got from the divorce. Tiger lost several endorsement deals, including, General Motors, AT&T and Gatorade.

2 Prince Charles and Diana


1 Brad Pitt and Jennifer Aniston

Brad Pitt and Jennifer Aniston were married in Malibu, on July 29, 2000, in a lavish wedding. Initially, many felt they were soul mates and the perfect couple that would last forever. However, things changed when Brad Pitt met Angelina Jolie. Brad and Jennifer divorced on October 5th, 2005. Not only did Brad break Jennifer's heart, he broke the heart of millions of people all over the world. The couple that was supposed to last forever, only lasted 7 years. There were intense rumours that Brad had been unfaithful with Angelina. He claims that he never cheated on Jennifer but that he did fall in love with Angelina during the filming of Mr. and Mrs. Smith. The speculation and media coverage was extremely intense. Rumors circulated that the split happened because Jen didn't want kids. Aniston denied that as the reason later in an interview. She also described her time with Brad as, "seven very intense years." Many accused Angelina of being responsible for the end of Brad and Jen. Their split received intense attention and most people took sides. "Team Aniston" and "Team Jolie" shirts became very popular, with the Aniston shirts selling out the Jolie shirts. However, Brad and Jen are now on amicable terms.

More in Celebrity Divorce