10 Toxic Breakups That Escalated Quickly
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VOICE OVER: Rebecca Brayton
WRITTEN BY: Don Ekama
Celebrity relationships can turn toxic in the blink of an eye. From shocking infidelities to public feuds, we're diving into the most dramatic and explosive breakups that captured headlines and left fans stunned. Our countdown explores the most notorious splits, including the tumultuous stories of Johnny Depp and Amber Heard, Chris Brown and Rihanna, and Britney Spears and Justin Timberlake. These relationships went from passionate love to bitter public battles that shocked the world!
10 Toxic Breakups That Escalated Quickly
Welcome to MsMojo, and today we’ll be looking at the most bitter celebrity breakups that unfolded rather quickly in the public eye and seemed to drag on endlessly.
Zach Bryan & Brianna “Chickenfry” LaPaglia[a]
Country music star Zach Bryan and podcaster Brianna “Chickenfry” LaPaglia went public with their relationship in July 2023. Just over a year later though, Bryan ended things, sharing an Instagram Story that suggested it was an amicable split. However, LaPaglia claimed she was blindsided by the news, and accused Bryan of mistreating her emotionally. Reports soon emerged that the singer allegedly offered her $12 million and an apartment in New York to keep quiet about their relationship. The breakup quickly turned messy, involving others like LaPaglia’s co-host Dave Portnoy, who released a diss track comparing Bryan to Sean “Diddy” Combs. UFC fighter Dave Onama was also allegedly paid to troll LaPaglia by giving Bryan a shoutout in her presence.
Halle Berry & Gabriel Aubry[b]
Celebrity breakups can be messy, but they become even messier when children are involved. That was the case for actress Halle Berry and Canadian model Gabriel Aubry, whose custody battle over their daughter turned ugly. After going their separate ways in 2010, tensions between the pair escalated when Berry, who was then dating French actor Olivier Martinez, sought to move to France with their daughter to be with him. A judge denied the request, and shortly after, Aubry and Martinez got into a physical altercation, allegedly due to Martinez threatening Aubry’s life for opposing the move. Ultimately, Berry was ordered to pay Aubry $16,000 monthly child support and over $400,000 in attorney fees, an arrangement she referred to as extortion.
Sandra Bullock & Jesse James
2010 was a particularly tumultuous year for Sandra Bullock. One moment, she was on top of the world, capping an impressive awards season with every actor’s dream: an Oscar. The next minute though, she was plunged into the depths of despair when news emerged that her husband, Jesse James, had been unfaithful. What began as one reported affair quickly ballooned into multiple allegations, with several women coming forward, claiming they had also been involved with James. This scandal overshadowed Bullock’s achievement, forcing her to cancel several promotional appearances for her film due to “unforeseen personal reasons.” However, she wasted no time in ending things. Just one month after the revelations, Bullock filed for divorce, which was finalized soon after.
Mariah Carey & Tommy Mottola
Mariah Carey’s remarkable career began after she was signed by the head of Columbia Records, Tommy Mottola. While working on her self-titled debut album, Carey began dating Mottola, and the two tied the knot in a lavish ceremony in 1993. But while things seemed glamorous on the surface, their marriage was far from idyllic. Mottola reportedly exerted tight control over Carey’s life, and left her feeling like a prisoner in their home. As Carey’s career soared, she started pushing for more creative and personal freedom, but Mottola kept resisting. Their conflicts soon spilled over into the public, as Carey began an affair with baseball player Derek Jeter. By 1996, the marriage completely unraveled and the two went their separate ways.
Alec Baldwin & Kim Basinger
Remember what we said about celebrity breakups being made worse when children are involved? Few instances of that are as notorious as Alec Baldwin and Kim Basinger. The pair exchanged vows in 1993 after meeting on the set of “The Marrying Man.” Initially seen as a Hollywood power couple, they quickly turned bitter enemies after their marriage soured in 2000. At the core of their conflict was their daughter, Ireland, over whom the couple fought a seven-year custody battle. As high-profile figures, their accusations and insults consistently made it into the press. Things got out of hand in 2007, when Baldwin’s infamous voicemail calling Ireland a “rude, thoughtless little pig” went public. While they eventually settled the dispute, neither emerged from the ordeal unscathed.
Angelina Jolie & Brad Pitt
The relationship between Angelina Jolie and Brad Pitt began with a contentious divorce and ended with one that was even more so. Following his high-profile split from Jennifer Aniston, Pitt began dating Jolie, and they married in 2014. Along the way, they had six children and became one of Hollywood’s most beloved couples. However, their marriage quickly crumbled and just two years later, Jolie filed for divorce following an alleged physical altercation on a plane. Since then, they have been embroiled in a lengthy custody battle over their children, further complicated by a legal dispute over a French winery they both shared. Although their divorce was finalized in 2019, the custody arrangements over their underage children remain a source of friction.
Kim Kardashian & Kanye West
This was one of pop culture’s most talked-about marriages and divorces. Before tying the knot in 2014, Kim Kardashian and Kanye West were already heavyweights in their respective fields, so their union made them a powerhouse couple. But personal issues and controversies strained their relationship, so in 2021, Kardashian filed for divorce. While the custody dispute over their four children wasn’t as messy as one would’ve imagined, West took issue when Kardashian began dating Pete Davidson, and launched relentless online attacks at him. This began to bleed into his music, and led to his removal as a performer at the 2022 Grammys. By the end of that year, their divorce was finalized, with the pair sharing custody of their children.
Britney Spears & Justin Timberlake
In the late ‘90s and early 2000s, pop music found its latest obsession: Britney Spears and Justin Timberlake. The couple, both at the height of their careers, dated until 2002, when a cloud of infidelity rumors involving Spears emerged. These rumors gained traction with the release of Timberlake’s hit song “Cry Me a River” whose music video featured a Spears lookalike. Though they weren’t married, their breakup was as public and bitter as a high-profile divorce. The media cast Spears as the villain, while she stayed largely silent, only responding through her song “Everytime.” Meanwhile, Timberlake largely benefited from the sympathy, using it to propel his solo career. In 2021, he issued a public apology to Spears for his behavior following their split.
Chris Brown & Rihanna
In the early hours of February 8th 2009, news broke that Chris Brown and Rihanna had been involved in a domestic dispute. The pair was set to perform at the Grammy Awards that evening, but had their appearances canceled after pictures of Rihanna’s bruised face flooded the media and Brown turned himself in to the police. Prior to this incident, Brown and Rihanna were one of music’s biggest couples, with an undeniable chemistry, but all of that unraveled literally overnight. Brown pleaded guilty to felony assault, receiving five years of probation and a restraining order from Rihanna. Although they briefly reconciled in 2013, the reunion was short-lived, and they parted ways for good a few months later.
Johnny Depp & Amber Heard
These Hollywood actors tied the knot in 2015 after meeting on the set of the 2011 film “The Rum Diary.” But their marriage only lasted about a year before Heard filed for divorce, accusing Depp of domestic violence, which he vehemently denied. The couple managed to reach a settlement that year, with Heard receiving a $7 million settlement. However, their dispute was reignited in 2018 when Heard wrote an op-ed reiterating her claims of domestic violence, leading Depp to sue her for defamation. Heard countersued, and the resulting trial became a media circus. Shocking allegations of violence and toxic behavior dominated headlines. Eventually, Heard was found liable for defaming Depp, awarding him significant damages, but the saga left both their reputations deeply tarnished.
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Welcome to MsMojo, and today we’ll be looking at the most bitter celebrity breakups that unfolded rather quickly in the public eye and seemed to drag on endlessly.
Zach Bryan & Brianna “Chickenfry” LaPaglia[a]
Country music star Zach Bryan and podcaster Brianna “Chickenfry” LaPaglia went public with their relationship in July 2023. Just over a year later though, Bryan ended things, sharing an Instagram Story that suggested it was an amicable split. However, LaPaglia claimed she was blindsided by the news, and accused Bryan of mistreating her emotionally. Reports soon emerged that the singer allegedly offered her $12 million and an apartment in New York to keep quiet about their relationship. The breakup quickly turned messy, involving others like LaPaglia’s co-host Dave Portnoy, who released a diss track comparing Bryan to Sean “Diddy” Combs. UFC fighter Dave Onama was also allegedly paid to troll LaPaglia by giving Bryan a shoutout in her presence.
Halle Berry & Gabriel Aubry[b]
Celebrity breakups can be messy, but they become even messier when children are involved. That was the case for actress Halle Berry and Canadian model Gabriel Aubry, whose custody battle over their daughter turned ugly. After going their separate ways in 2010, tensions between the pair escalated when Berry, who was then dating French actor Olivier Martinez, sought to move to France with their daughter to be with him. A judge denied the request, and shortly after, Aubry and Martinez got into a physical altercation, allegedly due to Martinez threatening Aubry’s life for opposing the move. Ultimately, Berry was ordered to pay Aubry $16,000 monthly child support and over $400,000 in attorney fees, an arrangement she referred to as extortion.
Sandra Bullock & Jesse James
2010 was a particularly tumultuous year for Sandra Bullock. One moment, she was on top of the world, capping an impressive awards season with every actor’s dream: an Oscar. The next minute though, she was plunged into the depths of despair when news emerged that her husband, Jesse James, had been unfaithful. What began as one reported affair quickly ballooned into multiple allegations, with several women coming forward, claiming they had also been involved with James. This scandal overshadowed Bullock’s achievement, forcing her to cancel several promotional appearances for her film due to “unforeseen personal reasons.” However, she wasted no time in ending things. Just one month after the revelations, Bullock filed for divorce, which was finalized soon after.
Mariah Carey & Tommy Mottola
Mariah Carey’s remarkable career began after she was signed by the head of Columbia Records, Tommy Mottola. While working on her self-titled debut album, Carey began dating Mottola, and the two tied the knot in a lavish ceremony in 1993. But while things seemed glamorous on the surface, their marriage was far from idyllic. Mottola reportedly exerted tight control over Carey’s life, and left her feeling like a prisoner in their home. As Carey’s career soared, she started pushing for more creative and personal freedom, but Mottola kept resisting. Their conflicts soon spilled over into the public, as Carey began an affair with baseball player Derek Jeter. By 1996, the marriage completely unraveled and the two went their separate ways.
Alec Baldwin & Kim Basinger
Remember what we said about celebrity breakups being made worse when children are involved? Few instances of that are as notorious as Alec Baldwin and Kim Basinger. The pair exchanged vows in 1993 after meeting on the set of “The Marrying Man.” Initially seen as a Hollywood power couple, they quickly turned bitter enemies after their marriage soured in 2000. At the core of their conflict was their daughter, Ireland, over whom the couple fought a seven-year custody battle. As high-profile figures, their accusations and insults consistently made it into the press. Things got out of hand in 2007, when Baldwin’s infamous voicemail calling Ireland a “rude, thoughtless little pig” went public. While they eventually settled the dispute, neither emerged from the ordeal unscathed.
Angelina Jolie & Brad Pitt
The relationship between Angelina Jolie and Brad Pitt began with a contentious divorce and ended with one that was even more so. Following his high-profile split from Jennifer Aniston, Pitt began dating Jolie, and they married in 2014. Along the way, they had six children and became one of Hollywood’s most beloved couples. However, their marriage quickly crumbled and just two years later, Jolie filed for divorce following an alleged physical altercation on a plane. Since then, they have been embroiled in a lengthy custody battle over their children, further complicated by a legal dispute over a French winery they both shared. Although their divorce was finalized in 2019, the custody arrangements over their underage children remain a source of friction.
Kim Kardashian & Kanye West
This was one of pop culture’s most talked-about marriages and divorces. Before tying the knot in 2014, Kim Kardashian and Kanye West were already heavyweights in their respective fields, so their union made them a powerhouse couple. But personal issues and controversies strained their relationship, so in 2021, Kardashian filed for divorce. While the custody dispute over their four children wasn’t as messy as one would’ve imagined, West took issue when Kardashian began dating Pete Davidson, and launched relentless online attacks at him. This began to bleed into his music, and led to his removal as a performer at the 2022 Grammys. By the end of that year, their divorce was finalized, with the pair sharing custody of their children.
Britney Spears & Justin Timberlake
In the late ‘90s and early 2000s, pop music found its latest obsession: Britney Spears and Justin Timberlake. The couple, both at the height of their careers, dated until 2002, when a cloud of infidelity rumors involving Spears emerged. These rumors gained traction with the release of Timberlake’s hit song “Cry Me a River” whose music video featured a Spears lookalike. Though they weren’t married, their breakup was as public and bitter as a high-profile divorce. The media cast Spears as the villain, while she stayed largely silent, only responding through her song “Everytime.” Meanwhile, Timberlake largely benefited from the sympathy, using it to propel his solo career. In 2021, he issued a public apology to Spears for his behavior following their split.
Chris Brown & Rihanna
In the early hours of February 8th 2009, news broke that Chris Brown and Rihanna had been involved in a domestic dispute. The pair was set to perform at the Grammy Awards that evening, but had their appearances canceled after pictures of Rihanna’s bruised face flooded the media and Brown turned himself in to the police. Prior to this incident, Brown and Rihanna were one of music’s biggest couples, with an undeniable chemistry, but all of that unraveled literally overnight. Brown pleaded guilty to felony assault, receiving five years of probation and a restraining order from Rihanna. Although they briefly reconciled in 2013, the reunion was short-lived, and they parted ways for good a few months later.
Johnny Depp & Amber Heard
These Hollywood actors tied the knot in 2015 after meeting on the set of the 2011 film “The Rum Diary.” But their marriage only lasted about a year before Heard filed for divorce, accusing Depp of domestic violence, which he vehemently denied. The couple managed to reach a settlement that year, with Heard receiving a $7 million settlement. However, their dispute was reignited in 2018 when Heard wrote an op-ed reiterating her claims of domestic violence, leading Depp to sue her for defamation. Heard countersued, and the resulting trial became a media circus. Shocking allegations of violence and toxic behavior dominated headlines. Eventually, Heard was found liable for defaming Depp, awarding him significant damages, but the saga left both their reputations deeply tarnished.
What did you think of these nasty celebrity breakups? Let us know in the comments below.
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