Actors Who Broke Up and Kept Sharing the Screen — the Films and Shows They Made Anyway

Shahid Kapoor and Kareena Kapoor. The definitive entry in this category. They had been together for roughly three years when Imtiaz Ali's film went into production, and the relationship ended before it was finished — leaving two actors to complete a romantic comedy, and then a promotional tour, as exes. Both have since described that stretch as the hardest work of their careers. What survives is a film in which Geet talks continuously and Aditya says almost nothing, and which nearly twenty years on is still the Hindi romance every subsequent one is measured against.

Ranbir Kapoor and Deepika Padukone. They had been Bollywood's most photographed young couple, they split around 2009 — after making Bachna Ae Haseeno together the year before — and then went back and did two more films as exes, this one and Tamasha. Ayan Mukerji's film is the one that worked, on every axis: it reset Deepika's career, gave Ranbir the most likeable character he has played, and remains a fixture of Indian streaming charts a decade later. Both are now married to other people, which somehow makes it easier to watch rather than harder.

Brad Pitt and Angelina Jolie. The inverse of everything else here — the film is where the relationship started rather than where it ended. They met making Doug Liman's 2005 action comedy about married assassins, were together for eleven years and married in 2014, and separated in 2016 with legal proceedings that ran for years afterwards. They made By the Sea in 2015, which Jolie wrote and directed, and which was received as a marriage being examined in public. Mr. & Mrs. Smith is the fun one; By the Sea is the other one.

Robert Pattinson and Kristen Stewart. Five films, four years, and a relationship conducted almost entirely inside the world's most invasive press cycle. They were together for most of the saga's run and had separated by the time Breaking Dawn – Part 2 finished its release. Both have spent the decade since building deliberately un-Twilight careers — hers in independent film and an Oscar nomination for Spencer, his through The Lighthouse, Tenet and The Batman. Pattinson joins Dune: Part Three in December.

Naga Chaitanya and Samantha Ruth Prabhu. The hardest one on the list. They met on Ye Maaya Chesave in 2010, married in 2017, and made this 2019 drama about a failed cricketer and the wife who holds a broken marriage together — a film whose entire emotional weight rests on the audience believing the couple. They announced their separation in October 2021 and divorced. Chaitanya married Sobhita Dhulipala in December 2024; Samantha married filmmaker Raj Nidimoru in December 2025. Four films together in all, including Autonagar Surya and Manam.

Milo Ventimiglia and Alexis Bledel. Jess and Rory dated on screen and the actors dated off it, for around three years starting in 2002 — and after it ended he kept returning to the show as a recurring guest, which meant playing the great unresolved love of a character played by his ex. Ventimiglia went on to This Is Us, Bledel to The Handmaid's Tale. The Netflix revival in 2016 brought them both back for another round.

Adam Brody and Rachel Bilson. Seth and Summer were the reason a lot of people stayed with The O.C. after the first season, and the two actors were together for around three years while making it — then broke up with two seasons still to shoot, and finished the run as television's most beloved couple anyway. Brody's career had its second act with Fleishman Is in Trouble and Nobody Wants This; both have been notably gracious about the show in every interview since.

Ryan Phillippe and Reese Witherspoon. They had met a year before the shoot and married in 1999, the year Roger Kumble's Dangerous Liaisons update opened, with Phillippe playing the seducer and Witherspoon the innocent he is wagered against. They separated in 2006 and divorced in 2008. Witherspoon has since won an Academy Award and built one of the most powerful production companies in television; Cruel Intentions is the artefact from the period when they were the couple.

Zac Efron and Vanessa Hudgens. Three films, a Disney Channel phenomenon that outgrew the channel entirely, and a relationship that ran from 2005 to 2010 — through the entire trilogy and out the other side. Both spent years afterwards being asked about it in interviews that were ostensibly about other films. Hudgens married baseball player Cole Tucker in 2023.

Johnny Depp and Winona Ryder. Tim Burton's 1990 film cast them as the outcast and the girl who sees him, and they were engaged during it — one of the most documented young-Hollywood relationships of its era, right down to a tattoo. It ended in 1993. The film has outlasted all of it and is now the closest thing American cinema has to a fairy tale of its own making.

Ranbir Kapoor and Katrina Kaif. Anurag Basu's musical adventure took four years to make, and the couple at the centre of it separated somewhere in the middle — so what reached cinemas in 2017 was a film built around a partnership that no longer existed, promoted by two people doing interviews about it. It flopped. Both have said since that finishing it was miserable. Katrina Kaif married Vicky Kaushal in 2021; Ranbir Kapoor married Alia Bhatt in 2022.