Hollywood's most surprising splits of all time

After making their first red carpet appearance together in 1999, Brad Pitt and Jennifer Aniston ignited a media frenzy, especially after their star-studded, lavish Malibu wedding the following year. With Brad arguably at peak heartthrob status after films like Fight Club, and Jen serving as Hollywood’s ultimate style muse, the couple was a match made in showbiz heaven.

After nearly five years of marriage, Brad and Jen announced their divorce in a joint statement – and although it seemingly resulted in the love triangle of the century after it was reported Brad left Jennifer for Angelina Jolie, the former Friends actress has stressed they were already divorced when the relationship began.

“It was such juicy reading for people,” she said in a 2025 interview with Vanity Fair. “It’s a shame that it [media frenzy] had to happen, but it happened”. She detailed that her approach to dealing with the drama was to “just pick yourself up by the bootstraps and keep on walking, girl” – words to live by!

Chris Pratt and Anna Faris met on the set of Take Me Home Tonight in 2007, when Anna was still married to her first husband, actor Ben Indra. After finalising her divorce in 2008, Anna became engaged to Chris later that same year, culminating in an intimate wedding in Bali in 2009. Both popular comedy actors, the couple was seen as super down-to-earth, often exchanging playful banter on red carpets and sharing sweet insights into their relationships during interviews.

The pair announced their shock split in 2017, stating that they would be co-parenting their son Jack, who was born in 2012. While the announcement was mature and respectful, fans were heartbroken that such a “real” couple was parting ways.

Speaking to Extra, Anna stressed that remaining amicable with Chris and co-parenting their son was “hugely important”, adding “we are great, and there’s so much friendship and love, and we surround Jack with love…he is really happy”.

“Bennifer” fans, strap in – we know it’s been a tumultuous ride. Ben Affleck and Jennifer Lopez met on the set of Gigli in 2002, where they played literal partners in crime. J-Lo was married to Cris Judd at the time, but filed for divorce that same year and began a whirlwind romance with Ben, with the couple getting engaged in November.

Following intense media pressure, the pair initially postponed their highly anticipated nuptials before officially announcing their breakup in early 2004, shocking those who had been expecting a fairytale wedding in the near future. But the couple couldn’t stay away, and after nearly two decades apart, we got Bennifer 2.0, with the pair having their long-awaited wedding in 2022.

J-Lo ended up filing for divorce two years later, with a source telling People magazine, “She tried really hard to make things work and is heartbroken”. And if that wasn’t enough of a rollercoaster, the duo were then spotted in September 2024 at a PDA-filled lunch in Beverly Hills, sparking hope of a rekindled relationship, though their divorce still went ahead.

The exes have since worked together on Kiss of the Spider Woman, which stars J-Lo and is being executive-produced by Ben. “It was a really tough time,” Jennifer recently admitted in a candid interview, adding that acting in the film helped take her mind off things. “It was hard not to think about stuff, but it was like the best and the worst of times, in a way.”

Another Ben Affleck relationship that captured the media was the actor’s marriage to Jennifer Garner, whom he met initially on the set of Pearl Harbor in 2001. The pair began dating after Ben and J-Lo called off their engagement, and after Jennifer divorced her first husband, actor Scott Foley.

The couple married in a super intimate ceremony on the Turks and Caicos Islands in 2005, and welcomed three children over the course of their decade-long marriage. In 2015, Ben and Jennifer jointly filed for divorce; while rumours circulated about Ben’s alleged affair with the couple’s nanny, Jennifer set the record straight during a 2016 interview with Vanity Fair, stating, “We had been separated for months before I ever heard about the nanny. She had nothing to do with our decision to divorce.

“The main thing is these kids – and we’re completely in line with what we hope for them.” The pair have since been praised for their harmonious co-parenting, with Ben calling Jennifer “wonderful and great” in a recent GQ profile. While it wasn’t meant to be, the actors have set a gold standard for co-parenting in the public eye.

2025 has proven to be a difficult year for celebrity breakups – after a nine-year on-and-off relationship, Katy Perry and Orlando Bloom also called it quits this year following a six-year engagement.

A source close to the couple told Us Weekly that they were “very much still in touch” and continuing to co-parent their daughter, Daisy Dove, together. “Orlando brought Daisy to meet Katy on tour before heading to the Bezos’ wedding. It’s not messy between them.” The split was said to be a relief for Katy, who didn’t want to go through a second divorce, especially during her ongoing Lifetimes tour.

While the duo initially broke up in 2017, following a brief one-year relationship, they later reconciled and were engaged in 2019, seemingly living out the picture-perfect love story, making it all the more difficult for fans when they finally called it quits.

After an initial high-profile marriage to Nicole Kidman (who can forget the images of Nicole leaving her attorney’s office), Tom Cruise once again made headlines with his relationship with Dawson’s Creek alum Katie Holmes. The actor generated an absolute media storm when he jumped on the sofa during an appearance on The Oprah Winfrey Show in 2005 and professed his love for Katie, and the couple announced both their engagement and pregnancy that same year.

After the birth of their daughter Suri in 2006, the pair tied the knot in a Renaissance-era castle on the coast of Bracciano, Italy. But after six years of marriage, Katie filed for divorce, shocking fans who perceived them as the ultimate loved-up couple.

Citing “irreconcilable differences”, Katie was also granted full custody of Suri and set out clear divorce terms with Tom, with Katie expressing a desire to protect her daughter from Scientology, which Tom has been a devout follower of. Suri, now 19, has not been spotted with her dad since 2012, fueling rumours of an ongoing estrangement with Tom.

After Brad’s split from Jennifer Aniston, he went public with his relationship with Angelina Jolie in 2005, after the pair met while filming Mr. and Mrs Smith in 2003. After rumours of a previous love triangle, “Brangelina” fever swept the media, and the couple continued to attract intense public attention.

After four high-profile adoptions and the birth of their twins in 2008, the pair announced their engagement in 2012 and enjoyed a storybook wedding at a chateau in the South of France. However, Angelina filed for divorce in 2016, citing “irreconcilable differences”, fueling a years-long divorce and custody battle, which was finally settled in 2024.

The pair has been notoriously tight-lipped about the circumstances of their breakup. In an interview with The Hollywood Reporter in 2024, Angelina declined to comment on the status of their divorce, adding later that she’s “trying to get used to what to share” about her private life. Brad is currently dating Ines de Ramon, an executive in the luxury jewellery sphere, while Angelina has not publicly stepped out with anyone since her divorce.

The couple that introduced “conscious uncoupling” to our lexicon, Gwyneth Paltrow, met Coldplay frontman Chris Martin backstage at one of his shows in 2002, and the couple tied the knot the following year in an ultra-private ceremony in Santa Barbara, California. The Shakespeare in Love actress and the Paradise singer welcomed daughter Apple in 2004 and son Moses in 2006, and continued to be a high-profile celebrity pairing despite their relatively private lives.

The pair remained close throughout their shock divorce proceedings, dubbed by Gwyneth as a “conscious uncoupling” via a blog post on her website, Goop. Gwyneth is now married to writer and director Brad Falchuk, while Chris was most recently in a long-term relationship with Madame Web actress Dakota Johnson, with the pair splitting in 2025 following eight years together.

The pair have remained on excellent terms, co-parenting their children and frequently showing support for each other. Gwyneth shared a sweet series of posts for Chris’ birthday, writing “Happy Birthday to the man that gave me these beautiful, wonderful human beings, we [heart you, Chris]”.