44 Of The Biggest Celebrity Breakups Of All Time

More painful than experiencing a breakup of your own is experiencing a breakup of a celebrity couple you loved.

Truly, is there anyone closer to us than the bond we feel with celebrities like Kim and Kanye West? I could easily put Ariana Grande’s relationships higher and writing importance above my own family members. Miley Cyrus and Liam Hemsworth’s marriage falling apart is more painful than my own parent’s divorce. We live, we pick up the pieces, and we learn to love again.

When celebrities break our hearts by separating from partners we hoped would they be with forever, it truly rocks the nation to its core?

These top celebrity breakups made headlines for weeks as we coped with the major losses. Together, we can unite once more in remembrance of them.


1. Brad Pitt and Angelina Jolie

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Brad Pitt and Angelina Jolie were a couple from 2005 to 2016 and have six kids together. 

2. Katie Holmes and Tom Cruise

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They were married for 5 years and have one child together, Suri Cruise.

3. Kim Kardashian and Kanye West

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Kim and Kanye are the most recent celebrity breakup. The pair began dating in April 2012 and filed for divorce in February 2021. Don’t know if anyone will be truly happy again.

4. Blake Lively and Penn Badgley

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Blake and Penn (also known as Serena and Dan) dated after meeting on the set of the hit show Gossip Girl. They dated for 3 years, from 2007-2010.

5. Johnny Depp and Amber Heard

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Johnny Depp and Amber Heard began dating in 2012, wed in February 2015, and eventually divorced after the couple both claimed the other was abusive.

6. Justin Beiber and Selena Gomez

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This couple was together sporadically from 2010 to 2018. Justin then married Hailey Baldwin in 2018.

7. Jim Carrey and Jenny McCarthy.

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Comedian Jim Carrey and Playboy model Jenny dated from 2005 to 2010. The separation was amicable.

8. Halsey and G-Eazy

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Halsey and G-Eazy dated for a year before breaking up in 2018. She wrote a song called “Without Me” which implied G-Eazy had cheated. 

9. Ariana Grande and Mac Miller.

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Mac and Ariana dated from 2016 to 2018. The pair broke up “because of their busy schedules.” Mac passed away in September 2018 and Ariana has repeatedly made tributes to him.

10. Jennifer Garner and Ben Affleck

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This couple married in 2005 and divorced in 2018. The couple share three children together.

11. Channing Tatum and Jenna Dewan.

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Channing and Jenna married in 2010 after meeting on the set of Step Up and divorced in 2019.

12. Chris Pratt and Anna Faris.

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Anna and Chris were together from 2007 to 2017. Their divorce was shocking to fans and to me, who worked at the grocery store they used to shop at.

13. Orlando Bloom and Miranda Kerr.

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Miranda Kerr and Orlando Bloom were together from 2007 to 2013 before she married Snapchat founder Evan Speigel.

14. Reese Witherspoon and Ryan Phillippe.

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The couple started dating in 1998, married in 1999, had finalized their marriage in 2008.

15. Miley Cyrus and Liam Hemsworth.

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Miley and Liam spent a decade together on and off before getting married in December 2018. They split in August of the same year.

16. Katy Perry and Russell Brand.

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Katy and Russell’s marriage ended after 14 months via text message.

17. Gwyneth Paltrow and Chris Martin.

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Paltrow met Martin backstage at a Coldplay concert in 2002. The couple married in 2003 and divorced in 2016. 

18. Britney Spears and Justin Timberlake.

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Britney and Justin were together in the late 90’s and early 00’s. They dated from 1999 to 2002. Justin featured a Britney lookalike in his music video “Cry Me A River,” which was pretty uncool.

19. Cardi-B and Offset.

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Cardi B and Offset were married in secret in 2017 and divorced in 2020. The couple share a daughter, Kulture.

20. Kristen Stewart and Robert Pattinson. 

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Robsten was a huge celeb couple who were on and off between 2008 and 2013.  The relationship ended after Stewart was photographed with another man, director Rupert Sanders.

21. Brad Pitt and Jennifer Anniston.

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Aniston and Pitt were married from 2000 to 2005, but together for 7 years total. The couple had an iconic reunion in 2020 as well. 

22. Nicki Minaj and Meek Mill.

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The pair was together from 2014 to 2016. The couple blamed the split on communication issues.

23. Mariah Carey and Nick Cannon.

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Nick and Mariah were married in 2008 and divorced in 2014. There were rumors that Cannon was unfaithful to Carey.

24. Jessica Simpson and Nick Lachey.

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Nick and Jessica met in the late 90’s at the Hollywood Christmas Parade. They were back and forth before marrying in 2002. The couple called it quits in 2005.

25. Miranda Lambert and Blake Shelton.

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This couple divorced in 2015 after 9 years together. Blake is now dating his co-judge from The Voice, Gwen Stefani.

26. Will Arnett and Amy Poehler.

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These two incredible comedians married in 2003 and separated in 2012. They have two sons together.

27. Taylor Swift and Calvin Harris.

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They dated for a whole year before breaking up. Heartbreaking! Harris accused Swift of “making him look bad” after it was revealed that she helped write his hit “This is what you came for.”

28. Bella Hadid and The Weeknd.

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Bella and The Weeknd started dating in 2015 and ended things in 2019. The pair is reportedly still friends.

29. Sarah Jessica Parker and Robert Downey Jr.

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The couple met on the set of the 1984 drama Firstborn when they were both 18. In 1991, after 7 years together, the couple split up. The split was blamed on Downey’s substance abuse issues.

30. Tim Burton and Helena Bonham Carter.

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Tim and Helena called it quits in 2014 after 13 years of marriage. The two met on the set of Planet of the Apes. They worked together in Big Fish, Corpse Bride, Charlie and the Chocolate Factory, Sweeney Todd: The Demon Barber of Fleet Street, Alice in Wonderland, and Dark Shadows.

31. JLO and Marc Anthony.

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The couple married in 2004, have two children together and separated in 2011. This was both Jen and Marc’s seventh marriage.

32. Kris Jenner and Caitlyn Jenner.

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The famous couple was together from 1991 until 2015. Caitlyn came out as transgender in 2015, two years after she and Kris announced their separation. 

33. Madonna and Sean Penn.

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Madonna and Sean were together from 1985 to 1989. The couple have two children together. 

34. Vanessa Hudgens and Zac Efron.

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Zac and Vanessa met on the set of High School Musical in 2005 and broke up in 2010.

35. Ryan Reynolds and Scarlett Johansson.

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Ryan and Scarlett met in 2005 and were married from 2008 to 2011. Ryan is now married to Blake Lively, with whom he has three daughters.

36. Ariana Grande and Pete Davidson.

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The SNL comedian and Thank u, next pop star dated, became engaged, and broke up within 2018.

37. Jeff and MacKenzie Bezos.

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Jeff and MacKenzie were together from 1993 to 2019. They divorced and she got $36.8 billion in the settlement.

38. Khloe Kardashian and Tristen Thompson.

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Khloe and Tristen were together from 2016 to 2019. The relationship ended after Tristen was seen with Jordan, another woman, and friend of the family’s. 

39. Liza Koshy and David Dobrik.

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The couple called it quits in 2018 through a long Youtube video.

40. Chris Brown and Rihanna.

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This tumultuous relationship lasted from 2008 to 2013.

41. Kylie Jenner and Tyga.

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Kylie and Tyga were together from Kylie’s 16th birthday in 2011 to November 2017. Kylie said she broke up with Tyga because she was young and wanted to experience more in life…or something like that.

42. Fergie and Josh Duhamel.

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Fergie and Josh split in September 2017 after 8 years of marriage. The couple is said to have broken up because they were total opposites. 

43. Antonio Banderas and Melanie Griffith.

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Antonio and Melanie were together for over 20 years before splitting in 2015.

44. Cher and Val Kilmer.

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Cher and Val dated from 1982 to 1984. The actor admitted in his 2020 memoir that he was dining at a restaurant when a waitress told him that Cher wanted to come over and meet him. 

Hannah Riley

Hannah Riley a comedy writer and content editor with ADHD living in Seattle, Washington.