10 Worst Celebrity Breakups in Hollywood: Justin Bieber-Selena Gomez to Brad Pitt-Jennifer Aniston

Pink Villa

30-05-2025

Celebrity breakups play out in public, and sometimes things can get messy, really messy. From page 3 headlines to diss tracks and sometimes even court dates, several aspects of the split amplify the drama, turning a normal separation into a full-blown media circus. When celebrity romances have a painful end, fans are always up for some tea, be it because of scandals, infidelity, or subtle unfollows.
Watching the downfall of what once seemed like a fairytale love story is captivating, and when famous faces are involved, tabloids dissect even the tiniest expression. Most painful breakups often involve a mix of emotional turmoil, public drama, and betrayal, and in some cases, the aftermath overshadows the entire relationship, no matter how beautiful it was at the start.
Over the years, several breakups in Tinseltown have shocked fans, but some were truly messiest, darkest, and jaw-dropping. Let's revisit 10 of the worst celebrity breakups and divorces in Hollywood.
Justin Bieber and Selena Gomez
Relationship Timeline: 2010 to 2018
How They Met: Bieber's then-manager, Scooter Braun, introduced him to Gomez in 2019
Why the Breakup Shocked Fans: Fans loved the couple, and there were numerous fan pages dedicated to the two, so when they parted ways, fans were heartbroken. And when Bieber moved on with model Hailey Baldwin within weeks, the Baby singer instantly became the most hated person on the internet.
Public Reaction: Even after seven years of their separation, the internet is not completely over their split. Fans blame Baldwin for copying Gomez and stealing Bieber from her, even today.
Where They Are Now: While Bieber is happily married to Baldwin and has welcomed a son, Gomez is dating Bieber's friend and producer Benny Blanco.
Gomez and Bieber, who were fondly called Jelena by their fans, left the internet divided with their split. Gomez released the song, Lose You to Love Me, which many believe was a direct response to the split. In the aftermath, the two have often left subtle shade and hidden messages in song lyrics and interviews. It seems that the online frenzy around their relationship and separation won't be ending anytime soon.
Kanye West and Kim Kardashian
Relationship Timeline: 2012 to 2022, tied the knot in 2014 and finalized divorce in 2022
How They Met: The pair met each other through a mutual friend during a song recording
Why the Breakup Shocked Fans: The drama surrounding their separation left fans disappointed and shocked. West, also known as Ye, made several explosive claims about Kardashian, and the latter accused the rapper of denying getting help for bipolar disorder
Public Reaction: Fans didn't see this split coming as they seemed like the perfect power couple. Ye's behavior post their separation also raised many eyebrows. The divorce also brought challenges of co-parenting to the front, as many saw Ye's emotional outbursts as damaging to their kids
Where They Are Now: Ye is currently dating Bianca Censori, and Kardashian briefly dated Odell Beckham Jr. and Pete Davidson post her split from the rapper
Kardashian and West's separation is undoubtedly one of the messiest celebrity breakups in recent history. They initially cited 'irreconcilable differences' as the reason for their split, but things quickly took a sad turn when the rapper launched multiple public attacks against the makeup mogul via social media and song lyrics.
Liam Hemsworth and Miley Cyrus
Relationship Timeline: 2009 to 2019, married in 2018 and they finalized their divorce in 2020
How They Met: They first met on the set of the movie The Last Song
Why the Breakup Shocked Fans: While Cyrus and Hemsworth kept the reason for their split a secret, many speculated that the actor cheated on the pop icon
Public Reaction: While some fans have expressed sympathy for the pair, many were critical of their choices and behaviors during their relationship and post their breakup
Where They Are Now: Hemsworth is currently dating Gabriella Brooks. Miley has been in a relationship with Maxx Morando since 2021
After being in an on-again, off-again relationship for over a decade, they tied the knot, but their marriage didn't even last a year. Cyrus' song Flowers is seen by many as a diss track for Hemsworth.
Johnny Depp and Amber Heard
Relationship Timeline: 2012 to 2016, tied the knot in 2015 but finalized divorce in 2017
How They Met: Depp and Heard met on the set of their shared 2011 film The Rum Diary
Why the Breakup Shocked Fans: The legal battles that followed their split made major headlines. The accusations of domestic violence and substance abuse, along with the highly publicized court battle in 2022, brought media and fan attention to their relationship
Public Reaction: The pair's 2022 trial became a media sensation, and the internet mostly sided with Depp. Social media buzzed with memes and viral content as the case unfolded in front of the public
Where They Are Now: Depp is reportedly dating a 28-year-old Russian model named Yulia Vlasova, while Heard isn't publicly dating anyone and is believed to be single. However, the actress welcomed her second child this month via surrogacy
Depp and Heard's split turned out to be one of the most contentious celebrity divorces of all time. Social media became a battleground for heated debates when the two went on trial for defamation. After Depp won the legal battle, Heard moved to Spain to get a new start.
Khloé Kardashian and Tristan Thompson
Relationship Timeline: 2016 to 2022
How They Met: They first met on a surprise blind date set up by their mutual friend Brandon Jennings
Why the Breakup Shocked Fans: Kardashian and Thompson's breakup was shocking for fans due to several cheating allegations and the fact that Thompson had fathered a child with another woman while Khloé was expecting their son via surrogacy
Public Reaction: Their split invited public scrutiny, especially because of Thompson's infidelity
Where They Are Now: While Kardashian is single and not looking to date, Thompson is currently dating someone, but her identity is not known to the public
Thompson cheated on Kardashian with her family friend Jordyn Woods. He later cheated on her with multiple other women, even fathering a child while the Good American founder was expecting via surrogate. The two are currently coparenting.
Joe Jonas and Sophie Turner
Relationship Timeline: 2016 to 2024, married in 2019
How They Met: The couple first met in October 2016 after Jonas sent her a message on social media
Why the Breakup Shocked Fans: Jonas and Turner's split was unexpected and sudden. The legal battles that followed their separation added to public drama
Public Reaction: The two faced a lot of criticism online post their breakup. The internet had mixed feelings for the two as their love story seemed like a fairytale until they announced they were parting ways
Where They Are Now: The pair is currently focused on coparenting their two daughters, Willa and Delphine. Jonas was linked to Stormi Bree in early 2024 and later with actress Laila Abdallah, but none of their relationships were confirmed, while Turner is currently dating Peregrine Pearson
The drama that followed their divorce was messy. Even though it started as a mutual split, things quickly turned sour as conflicting narratives started leaking to the media. Turner also filed a lawsuit against Jonas for withholding their children's passports to prevent them from returning to the UK with her.
Brad Pitt and Jennifer Aniston
Relationship Timeline: 1998 to 2005, married in 2000
How They Met: They first met in 1994 after their managers introduced them
Why the Breakup Shocked Fans: The media frenzy surrounding their divorce was intense, especially because of speculations of infidelity between Pitt and Angelina Jolie during the shoot of Mr. and Mrs Smith
Public Reaction: Their separation was highly publicized, and Aniston was initially seen as a "heartbroken ex." However, she moved on quickly and focused on her career to shut out the noise
Where They Are Now: After their split, Pitt started dating Jolie. Aniston and Pitt remained friends despite the nasty breakup, and they are often seen chatting during public events
Aniston and Pitt were seen as the perfect couple in Hollywood, and when they decided to part ways, fans couldn't keep calm. For years, fans labeled Jolie as the "other woman," and the love triangle became a hot topic of discussion among the media and fans.
Machine Gun Kelly and Megan Fox
Relationship Timeline: 2020 to 2024
How They Met: They met on the set of the film Midnight in the Switchgrass
Why the Breakup Shocked Fans: The couple announced their separation while Fox was expecting their first child together
Public Reaction: The timing of the split left many fans concerned. The reactions to their breakup were intense, with many siding with Fox
Where They Are Now: The two are currently focused on coparenting
When Fox revealed what she found on MGK's phone was "unforgivable," though she refused to disclose exactly what it was, fans knew that a reconciliation was not on the cards. Even though many speculate infidelity as the reason for them parting ways, the mystery remains unsolved.
Ben Affleck and Jennifer Lopez
Relationship Timeline: 2002 to 2004 and 2021 to 2024, married in 2022
How They Met: They first met on the set of Gigli
Why the Breakup Shocked Fans: When the couple reunited after two decades, fans were all hearts for the two. No one saw their split coming, and when it was publicly announced, many couldn't believe the news
Public Reaction: The two have been met with a generally supportive and respectful public reaction to their separation
Where They Are Now: The two are focusing on coparenting their kids
Their whirlwind romance and PDAs made them the ultimate power couple in Hollywood, but it seems that even the most promising relationships can crumble under intense media scrutiny and relentless paparazzi pressure.
Brad Pitt and Angelina Jolie
Relationship Timeline: 2005 to 2016, married in 2014
How They Met: They first met on the sets of Mr. and Mrs. Smith
Why the Breakup Shocked Fans: Their unexpected split sparked public debate and speculations about the reason for their separation
Public Reaction: The end of their relationship also marked the end of an era for many fans, with many questioning their previous image of a perfect couple
Where They Are Now: Pitt is currently in a relationship with Ines de Ramon. Jolie is not dating anyone right now and is focused on raising her kids
Pitt and Jolie's divorce was not amicable, with a lengthy and bitter custody battle casting a dark shadow on their relationship. Many of Pitt's children have dropped his last name legally.
Breakups and divorces are painful and heartbreaking, and when they play out in the public eye, it becomes even more challenging. Celebrities have it harder than normal people because every little detail is discussed and scrutinized by their fans and in media. While fans love to gush over their favorite stars, they should also be respectful and understanding when things aren't going too well with them. Messages of support and comforting comments can do magic.