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The 20 Saddest Celebrity Breakups Of The 2000s

Why couldn't they just stay together for the kids?!?! Note: this is a list based on emotional devastation, not on popularity. Please look elsewhere for your Brad and Jen coverage. *This post has been edited to remove a trans slur.*

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  • 1. Rachel McAdams and Ryan Gosling, 2007 and 2008

    WHAT DO YOU MEAN The Notebook isn't real?

  • 2. Britney and Justin, 2002

    It's all your fault, JT. All. Your. Fault.

  • 3. Jessica Simpson and Nick Lachey, 2005

    Poor Jess, she traded a lifetime of happiness for Adam Levine.

  • 4. Reese Witherspoon and Jake Gyllenhaal, 2009

    Say what you will about beards, but I believed.

  • 5. Chris Brown and Rihanna, 2009

    Upside: Riri is ok. Downside: 'Forever' is ruined.

  • 6. Adam Brody and Rachel Bilson, 2006

    WHAT DO YOU MEAN The OC isn't real???!?

  • 7. Lindsay Lohan and Samantha Ronson, 2008 and 2009

    Lindsay just needs someone to love her. Why is that so hard?

  • 8. The Original Bennifer, 2003

    Gigli: Never Forget.

  • 9. Michelle Williams and Heath Ledger, 2007

    And then things just got worse. Oof.

  • 10. Jude Law and Sienna Miller, 2004 and 2006

    Balthazar and the Nanny aside, these two belong together. (This one still counts even though they're kind of back together, because they wasted so much time apart. Life's too short, kids.)

  • 11. Bobby Brown and Whitney Houston, 2006

    Probably for the best? But still.

  • 12. Gisele Bundchen and Leonardo DiCaprio, 2005

    Ok, so Tom Brady is aging a lot better than Leo, but these were the golden days. Why can't a supermodel and a movie star work it out anymore?

  • 13. Paris Hilton and Nick Carter, 2004

    Did you read those love letters? And then he beat her up? Devastating.

  • 14. Elizabeth Hurley and Hugh Grant, 2000

    (For Jack). But if you can make it through a scandal, why can't you make it through unfortunate aging?

  • 15. Ed Norton and Salma Hayek, 2003

    A sad day for geeks the world over.

  • 16. Michelle Williams and Spike Jonze, 2009

    Noooooooooooooo she was finally happy and he loved Matilda and everything. They were the Brooklyn Dream!

  • 17. Kate Bosworth and Orlando Bloom, 2005

    She got soooo skinny (even skinnier than that) after he dumped her. And I think she had to share custody of the dogs? :(

  • 18. Susan Sarandon and Tim Robbins, 2009

    Who will lead us through the next decade of irrelevant celebrity protests? I am lost.

  • 19. Drew Barrymore and Fabrizio Moretti, 2007

    I just liked this Drew the best of all the 2000s' Drews. Also it feels very 2000s to date a Stroke.

  • 20. Mary Louise Parker and Billy Crudup, 2004

    What a fucking dick, you know?