48 Most Worst Exes in Hollywood Couples

When we watch Hollywood couples on screen, everything seems dreamy and perfect. However, no one knows the darker side! Several celebrities faced cheating scandals, heated arguments and domestic violence in their personal lives. While some celebs decide to wash their dirty laundry in public, many of them part ways amicably and respectfully.

The upcoming Netflix documentary “Worst Ex Ever,” is the spinoff to Worst Roommate Ever. As the title says, this true-crime docuseries takes viewers on a chilling journey of terrifying reality where exes are considered worse.

Before the new series goes on-air, let us explore some of the scandalous and ugly break-ups in Hollywood history.

Chris Brown and Rihanna

Chris Brown and RihannaChris Brown and Rihanna were an IT couple in the late 2000s. However, domestic violence put a break in their relationship. In 2009, Brown was arrested for assaulting Rihanna before the Grammy Awards. She was left bruised and swollen. Disturbing photos of her bruised eyes and black eyes were doing the rounds on the internet, which made Brown a pop culture villain. However they were back together in 2012, but their relationship didn’t last long. Now, the couple has moved on with their respective partners.

Tommy Lee and Pamela Anderson

Tommy Lee and Pamela AndersonFor Tommy Lee and Pamela Anderson, it was love at first sight. After 95 hours of knowing each other, they married in 1995 on a beach. They soon welcomed kids in 1996 and 1997. In 1998, Lee was arrested and charged with felony spousal abuse and child abuse. Their relationship highlights also included a tape and Pam claiming that she got Hepatitis C from Lee. She even called him a “disaster”. They broke up and were back together several times. Later, Lee moved on with Brittany Furlan.

Selena Gomez and Justin Bieber

Selena Gomez and Justin Bieber

Selena Gomez and Justin Bieber were among the cutest young couples in Hollywood. They started dating in 2010 and made their relationship official on New Year’s Eve 2011. After dating for two years, they parted ways in 2012. Although Gomez said she loved him, Bieber said they were not talking. Things went downhill in 2014 after Bieber got arrested for drunk driving and accused of vandalism. There were also rumors that he was cheating on Gomez. Although they got back together on several occasions (even after dating others in between), they parted ways in 2018 when Bieber married Hailey Baldwin.

Liam Hemsworth and Miley Cyrus

Liam Hemsworth and Miley Cyrus

Liam Hemsworth and Miley Cyrus had a rollercoaster romance. The couple fell in love while shooting the 2009 film The Last Song. After dating for a year, they broke up but soon reconciled and got engaged. However, they postponed their wedding indefinitely, which sparked breakup rumors. They even called off their engagement amid reports of Liam cheating on her. Later, they reunited and finally married in 2018. However, their relationship didn’t last long, as they filed for divorce in 2019.

Madonna and Sean Penn

Madonna and Sean PennMadonna and Sean Penn met on the Material Girl music video set. The duo got married in 1985. However, it was a turbulent marriage as the couple was involved in domestic disputes, one of which landed Madonna in the hospital. Penn was also charged with felony domestic assault, but later she dropped it. The couple got divorced in 1989.

Mike Tyson and Robin Givens

Mike Tyson and Robin Givens

Mike Tyson and Robin Givens got married in 1987, but their marriage fell apart within months. Givens suffered a miscarriage in the same year and filed for divorce. She accused the boxer of domestic abuse. On the other hand, the boxer countersued for annulment, claiming Givens trapped him into getting married by faking pregnancy. Tyson also claimed he caught his ex-wife Givens with Brad Pitt in bed. Tyson and Givens annulled their marriage in just a year.

Carmen Electra and Dennis Rodman

Carmen Electra and Dennis Rodman

Nine days after Carmen Electra and Dennis Rodman married, the latter filed annulment papers, saying he was not in a sound mind when he said his vows. The couple was in an on-and-off relationship despite getting divorced. However, the last straw was their domestic violence dispute, and they ended up getting arrested for misdemeanor battery in 1999.

Charlie Sheen and Denise Richards

Charlie Sheen and Denise Richards

Charlie Sheen and Denise Richards met in 2000, got married in 2002, and welcomed their children in 2004. However, Denise filed for divorce. During their child custody battle, Denise accused Charlie of inappropriate behavior.

Brooke Mueller and Charlie Sheen

Brooke Mueller and Charlie Sheen

Even years after their split, Brooke Mueller and Charlie Sheen were in the news for the custody of their twin children. Currently, Sheen’s ex-wife, Denise Richards, has custody of their children.

Charlie and Sheen had a tumultuous relationship. After meeting through mutual friends, the couple got married in 2008, and they have twin sons (2009). In 2009, the duo had a significant fight in Aspen, leading to Sheen’s arrest, and charged with two felonies, including second-degree assault, menacing, and criminal mischief for attacking Mueller. In 2010, Sheen filed for divorce, and the duo continued facing issues with Muller going to rehab several times and several incidents involving the police.

Michael Lohan and Kate Major

Michael Lohan and Kate Major

Michael and Kate had a rocky relationship. Kate has been battling alcohol issues, and recently, she was arrested and booked for violation of a protection order. Michael revealed to TMZ that he wants everyone to know what abuse, lies, and deceit look like and that men can be victims, too. He clarified in the interview that he was never abusive or violent.

Diane Lane and Josh Brolin

Diane Lane and Josh Brolin

Diane Lane and Josh Brolin had a turbulent relationship. Just four months after their marriage, Brolin was arrested and charged for hitting his wife. After this, they managed to keep their life low profile. However, Brolin was arrested for public intoxication on New Year’s 2013. The couple was married for almost a decade. The divorce was finalized in 2013.

Alec Baldwin and Kim Basinger

Alec Baldwin and Kim Basinger

Alec Baldwin and Kim Basinger were the most talked about couples in the 1900s. The duo got married in 1993 and welcomed a baby girl in 1995. However, their relationship didn’t last long. One of the reasons was Basinger’s agoraphobia and panic attacks and Baldwin’s temper- their different lifestyle choices contributed to more tension. The couple divorced in 2002. But even after divorce, their fight was far from over, they continued to fight over their daughter’s custody.

Kate Moss and Pete Doherty

Kate Moss and Pete Doherty

Kate Moss and Pete Doherty had a turbulent relationship. The couple started dating in 2005. Everyone knew about Dorherty’s drug addiction and Kate being a party animal. But what shocked everyone was Kate using cocaine while hanging out with Doherty. Her reputation was damaged, and she lost several lucrative modeling contracts. Things got chaotic, and the couple broke up following his failed stint at rehab in Arizona. Although they were back and ended up in rehab together, it didn’t last long, and their toxic relationship ended in 2007.

Lindsay Lohan and Samantha Ronson

Lindsay Lohan and Samantha Ronson

Lindsay Lohan and Samantha Ronson had an on-and-off relationship. The same-gender couple had become the talk of the town during their dating period in 2008. There were allegations that Sam used drugs and locked Lindsay out of her house. They even got into multiple public spats. Their relationship ended in 2009.

Jude Law and Sienna Miller

Jude Law and Sienna Miller

Jude Law and Sienna Miller began dating in 2003 and got engaged in 2004. But things got worse in 2005, when she learned about Law’s affair with his children’s nanny and called off their engagement. Although they broke up in 2006, they got back together in 2009, just to part ways again in 2011 as their relationship couldn’t survive his past infidelities.

Bobby Brown and Whitney Houston

Bobby Brown and Whitney Houston

In 1992, Whitney Houston married Bobby Brown. They were darlings of the music industry, creating what could be described as “Billboard chart heaven.” However, their relationship was a roller-coaster ride. Due to the drug addiction, rumors of infidelity, arrests, and physical abuse allegations, their marriage had become fodder for gossip columns. The couple got divorced in 2007.

Jenelle Evans and Courtland Rogers

Jenelle Evans and Courtland Rogers

Just after a month of getting married, Jenelle Evans filed for divorce with Courtland Rogers. Shortly after getting married, the couple got arrested on drug charges. After learning she was pregnant with Courtland’s child, she also underwent an abortion. The duo also had several domestic violence disputes.

OJ Simpson and Nicole Brown

OJ Simpson and Nicole Brown

Nicole Brown was OJ Simpson’s second wife. The couple married after dating for several years in 1985. They have two children. There were several times police were called to their residence, but on New Year’s Day (1989), it was the first time Simpson was arrested and charged with spousal abuse. Brown was injured and had a cut lip, a black eye, and a hand imprint on her neck. He pleaded no contest and was sentenced to community service, two years probation, and a fine. Brown filed for divorce in 1992. Their marriage lasted eight years.

The footballer accused Brown of having drug problems and a dual personality in his book. In 1994, Brown was found murdered in her house along with her friend Ronald Goldman, the main suspect being Simpson. Although he was arrested, he was found not guilty, but later, he was held responsible for the deaths in a civil suit.

Chad Ochocinco and Evelyn Lozada

Chad Ochocinco and Evelyn Lozada

The madly in love couple Chad Ochocinco and Evelyn Lozada filmed a reality show, but after they got married, Evelyn found out about her husband cheating on her. They got into an ugly fight, which left her bruised and battered. Chad was charged with domestic violence, and their show got cancelled. They filed for divorce just after 41 days of their marriage.

Jenna Jameson and Tito Ortiz

Jenna Jameson and Tito Ortiz

Porn star Jenna Jameson and UFC icon Tito Ortiz had a rocky relationship. In 2010, Ortiz was arrested for domestic abuse, but Jameson withdrew the charges later. In 2012, Jameson was arrested for driving under the influence. While celebrating her birthday, she was also arrested for battery. After the couple announced their split in 2013, Ortiz got custody of their kids.

Tom Sizemore and Heidi Fleiss

Tom Sizemore and Heidi Fleiss

Tom Sizemore and Heidi Fleiss started dating in the early 2000s. In 2003, Fleiss filed a complaint against Sizemore, accusing him of beating her and burning her with a cigarette. Sizemore was found guilty on six charges and served 90 days in jail.

Brad Pitt and Angelina Jolie

Brad Pitt and Angelina Jolie

Brad Pitt and Angelina Jolie, who met on the set of their action film Mr. and Mrs. Smith in 2004, got married in 2014, and announced their separation in 2016 after their violent argument on a plane. Popularly known as Brangelina, their ugly split and custody battle over children have been hitting the headlines for a long time.

In 2016, Brad Pitt got into an argument with their son Maddox in a private jet, and the next thing we get to know is Angie filing for divorce, accusing him of child abuse. Their second oldest son Pax called him a “World-class a**h**e and a “f***g awful human being.” Although the couple has remained silent about their divorce, their legal documents reveal ugly disputes, including disagreements over their shared winery, Miraval.

Ben Affleck and Jennifer Garner

Ben Affleck and Jennifer Garner

Ben Affleck and Jennifer Garner were known as one of Hollywood’s hottest couples, but their relationship didn’t last for long. After 13 years together, the couple announced their split in 2015. Reportedly, Garner had to go through a tough time managing Ben. Ben’s addiction issues made things worse and prompted fights. There were also rumors of Ben having an affair with the couple’s nanny, though he denied it.

Johnny Depp and Amber Heard

Johnny Depp and Amber Heard

Johnny Depp and Amber Heard met on the film The Rum Diary set in 2011. They seemed like head over heels in love, and the duo married in 2015. However, they soon called it quits. After filing for divorce, Heard filed a domestic restraining order against Depp, accusing him of domestic abuse charges. She claimed that he assaulted her on her birthday and said that his violent behavior was because of his alcohol and drug use. They divorced in 2016 and agreed on a $7 million divorce settlement. Things didn’t stop there, as in 2019, Depp sued Heard for defamation over her 2018 Washington Post op-ed. In 2022, their defamation trial was highly publicized, and much of it was livestreamed. Both of them made allegations of physical, emotional, and mental abuse against each other.

Kim Kardashian and Kanye West

Kim Kardashian and Kanye West

Kim Kardashian and Kanye West married in 2014, and their wedding was one of the most extravagant celebrity ceremonies. However, their marriage didn’t last long, as Kim filed for divorce in 2021. The rapper’s erratic behavior in 2016, his support for Donald Trump, and several controversial remarks (Twitter rants) strained their relationship. Kim had spoken about West’s bipolar diagnosis in 2020 and requested compassion and empathy as they were going through a tough time. In 2022, West accused Kim of cheating on him with Chris Paul and shared a series of tweets, which Kim refuted.  Despite her efforts to fix the marriage, their relationship couldn’t stand for long.

Ryan Phillippe & Reese Witherspoon

Ryan Phillippe & Reese WitherspoonRyan Phillippe and Reese Witherspoon met in the late 1990s, married within a few years, and even had kids. However, things didn’t seem to work out, and soon after welcoming their first baby, they went for couples therapy in 2002. The couple announced their separation in 2006. On why they ended their marriage, There were rumors that Witherspoon confronted Phillippe about his alleged infidelity. The media speculations and legal battles made their divorce ugly!

Tiger Woods and Elin Nordegren

Tiger Woods and Elin NordegrenTiger Woods and Elin Nordegren met in 2001, and three years later, the duo got married, welcoming kids in 2007 and 2009. The duo’s relationship didn’t last long because of a massive cheating scandal, with Wood’s reportedly having multiple affairs, including his relationship with Rachel Uchitel. He sought treatment for sex addiction. Finally, the duo got divorced in 2009.

Zayn Malik and Gigi Hadid

Zayn Malik and Gigi HadiZayn Malik and Gigi Hadid were one of the A-list couples. They were in an on-and-off relationship for almost six years. The couple welcomed a baby girl in 2020 but parted ways in late 2021, when there were reports of Hadid’s mother, Yolanda, claiming Malik struck her. However, Malik pled no contest.

Tom Cruise and Nicole Kidman

Tom Cruise and Nicole Kidman

Tom Cruise and Nicole Kidman’s ten years of marriage ended when Cruise filed for divorce. This left Nicole feeling humiliated. The couple had differences due to religious beliefs (Scientology) and other issues like where to go for vacations. There were also rumors that he was secretly gay, and their PDAs were just a cover-up for his sexuality. Nicole dismissed rumors that Cruise was gay. There was also gossip that he had an extramarital affair with a man. Chad Slater, a male pornographic actor, claimed that Nicole caught him with Tom, which led to their divorce. However, Tom denied it, saying he had never met the adult star. There were also reports that Nicole wasn’t keen on converting to Scientology. Although she didn’t want it, her kids were raised as Scientologists.

Britney Spears and Justin Timberlake

Britney Spears and Justin Timberlake

Britney Spears and Justin Timberlake dated each other at the peak of their careers in 1999. However, their relationship didn’t last long as they parted ways within three years in 2002 amid rumors of infidelity. His song “Cry Me a River,” sparked rumors suggesting Britney cheated on him.

Britney was disappointed with the music video. She had revealed that Justin didn’t want to be a father, and she had an abortion during their 3-year-relationship.

Britney Spears and Kevin Federline

Britney Spears and Kevin Federline

Britney Spears married Kevin Federline in 2004 but filed for divorce in 2006, claiming Kevin craved fame and fortune. However, Kevin resisted signing papers due to Britney’s behavior. She was in rehab during that time. In 2007, Britney had a public breakdown. She even shaved her head in front of paps. Her behavior led the court to give temporary custody of their sons to Kevin. In 2008, she was put on lockdown for a mental evaluation. The pop singer was also said to be under the influence of an unknown substance.

Sandra Bullock and Jesse James

Sandra Bullock and Jesse James

Sandra Bullock, who married Jesse James in 2005, was in a scandal because of her husband’s infidelity. Several women claimed to have affairs with their husbands, which is when they divorced them. Amidst these allegations, Jesse entered a treatment facility due to personal issues. During this challenging time, she even canceled events to promote her film. After Sandra filed for divorce, he went on to make a controversial statement, calling cheating a part of life!

Halle Berry and Gabriel Aubry

Halle Berry and Gabriel Aubry

Halle Berry and Gabriel Aubry were together for three years and welcomed a baby girl. However, three years later, they parted ways. It seems that their age difference was the main factor for their split. Also, reports suggest that Gabriel started getting attracted to other women, which didn’t feel right for him to stay with Halle. Gabriel’s friend alleged that Gabriel made threatening comments towards Halle and used a racial slur against her. Additionally, the custody battle got nasty as Gabriel got into a fist fight with Halle’s fiancé, which apparently left Gabriel with a fractured rib, bruises to the face, and cuts that needed stitches. However, it was Gabriel who got arrested for misdemeanor battery.

Robin Thicke and Paula Patton

Robin Thicke and Paula Patton

In 2005, Robin Thicke and Paula Patton got married. Robin’s marriage with Paula started falling apart, and he started using painkillers. After 21 years of staying together and nine years of marriage, Paula filed for divorce in 2014, alleging infidelity, physical abuse, and drug use. However, Robin denied cheating and abuse allegations. The couple also had a tough time battling custody of their son as they made severe accusations against each other.

Maria Shriver and Arnold Schwarzenegger

Maria Shriver and Arnold SchwarzeneggerMaria Shriver and Arnold Schwarzenegger met in 1977 and married in 1986. Their 25-year marriage ended after Arnold announced that he had fathered a child with his longtime housekeeper, Mildred Baena, and Maria filed for divorce. The betrayal deeply hurt Maria, and the incident was covered in the media, making their split ugly and messy.

Eminem and Kim Scott

Eminem and Kim ScottEminem and Kim Scott met each other in 1988 and got married in 1999. Eminem alleged that he caught Kim cheating on him, which made him hit the guy, landing him in jail for assault charges. Eminem, who earlier rapped about killing Kim, wrote another song about hurting her, after which she tried to end her life. After this incident, Eminem requested a divorce, while Kim responded by suing him for emotional distress. During 2000-2001, the duo split and got joint custody of their daughter. However, in 2006, they remarried and got divorced in three months.

Diane Kruger and Joshua Jackson

Diane Kruger and Joshua JacksonDiane Kruger and Joshua Jackson met in 2006. Although they were never married, they were together for several years, and their relationship grabbed extensive media attention. In 2015, there were rumors that Diane was seen kissing her Sky co-star Norman Reedus. However, the actors made no statements about the same. In 2016, they announced their split. As per Joshua, the duo broke up even before announcing their split.

Demi Lovato and Wilmer Valderrama

Demi Lovato and Wilmer Valderrama

Demi Lovato and Wilmer Valderrama met in 2010, and they had a 12-year age gap. During their relationship, they faced personal struggles, including Demi’s mental health and substance abuse issues. However, the duo parted ways in 2016. In an interview, the singer said that she was attracted to older men because of daddy issues and also added that the age gap was unhealthy and toxic (although she didn’t mention names, it was evident she was talking about Wilmer).

Fergie and Josh Duhamel

Fergie and Josh Duhamel

Fergie and Josh Duhamel got engaged in 2007 after dating for three years. The duo got married in January 2009. However, their marital bliss was short-lived as an exotic dancer. Nicole Forrester claimed Josh had s#x with her, but Josh denied the claims, calling the story ridiculous. Fergie was upset with rumors of cheating. After Nicole apologized to Fergie in 2010, the duo renewed their vows. However, in 2014, the duo announced their split.

Courteney Cox and David Arquette

Courteney Cox and David Arquette

Courteney Cox married David Arquette in 1999. However, in 2010, the couple agreed on trial separation. The day after announcing the separation, David said in an interview that they were not having s#x. In 2011, David had been to rehab for drinking and depression and not for drugs. The same year, Courtney had gone on a vacation with her daughter and her best friend, Josh Hopkins, but the media speculated scandalous happenings between Courtney and Josh. David clarified that there was no scandal. In 2012, the couple filed for divorce.

Cher and Sonny Bono

Cher and Sonny Bono

After being together for a decade, the music industry’s popular couple Cher and Sonny Bono parted ways in 1975. According to Cher, “involuntary servitude” was the reason behind their split. Things got worse when Cher accused Sonny of keeping her rightful earnings, and the latter responded by taking her to court for custody of their child. Tragically, Sonny passed away in 1988.

Tom Sandoval and Ariana Madix

Tom Sandoval and Ariana Madix

In 2014, Tom Sandoval and Ariana Madix confirmed their relationship. In 2019, Ariana felt Tom betrayed her trust after he shared her private story about her (he had revealed to his friends that Ariana and co-star Lala Kent had a sexual experience in his car). Although they got back together, in 2023, the couple split after she found out that Tom was cheating on her for six months with her friend Raquel Leviss. In 2024, she filed a case against Tom regarding selling their Los Angeles home.

Brandi Glanville and Eddie Cibrian

Brandi Glanville and Eddie Cibrian

Brandi Glanville and Eddie Cibrian got married in 2001. However, their relationship didn’t last long, as Brandi filed for divorce in 2009 after finding out about Eddie’s affair with the Blue musician LeAnn Rimes. He also apparently cheated on her with Vanderpump Rules star Scheana Shay.

Lala Kent and Randall Emmett

Lala Kent and Randall Emmett

Lala Kent and Randall Emmett, who got engaged in 2018, postponed their wedding, which led to speculation about a possible split, but their delay was because of the pandemic. After giving birth to their first baby in 2021, the couple planned to get married in 2022, but even before that, they parted ways after finding out that Randall had been cheating on her. He was photographed with two women in Nashville. Lala even claimed that Randall moved in with another woman just after she moved out. There were also reports that the producer offered a woman film role in exchange for s#x##l favors, but he denied it, claiming it was part of Kent’s “smear campaign”.

Iggy Azalea and Nick Young

Iggy Azalea and Nick Young

Iggy Azalea and Nick Young announced their engagement in 2015 but broke up a year later. The reason for the breakup was the video in which Nick was seen discussing his affair with another woman. Things got worse when Nick’s ex was four months pregnant with his daughter when the duo parted ways.

Kristen Stewart and Robert Pattinson

Kristen Stewart and Robert Pattinson

Kristen Stewart and Robert Pattinson met and fell in love while filming Twilight in 2008. However, their romance hit a rough patch in 2012, when photos of Kristen kissing the franchise director, Rupert Sanders, went viral. Although the couple got together, it was just for a short time, as they parted ways in 2014.

Judy Garland and Sidney Luft

Judy Garland and Sidney Luft

Judy Garland and Sidney Luft were attracted to each other (although they had other spouses) when they first met at a nightclub and married in 1952. However, their relationship was tumultuous, and they divorced in 1965, with Judy claiming that Sidney was frequently drunk and violent.

Marlon Brando and Rita Moreno

Marlon Brando and Rita Moreno

Marlon Brando and Rita Moreno were in a relationship for almost eight years. But their relationship was toxic. When Rita was pregnant, Marlon wanted an abortion. She was struggling in relationships so much that she attempted suicide. She said that he was a bad guy when it came to women. They made a movie together, and Marlon wanted to give their relationship another chance, but Rita didn’t want it.

If you think we forgot to mention any critical name or person, please let us know in the comments.

Nagarathna
Nagarathna
Nagarathna, who holds a master's degree in Biotechnology, is a dedicated and passionate freelancer and content writer. Before entering the freelance world, she was working with online media and publishing companies for several years as full-time content writer and proofreader. As an entertainment freak, she loves staying on top of trends. In her free time, she enjoys reading novels, listening to music, or blogging and vlogging, where she gets to share her insights about various topics, including gardening, relationships and other lifestyle subjects.
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