THG Presents: The Most Heartbreaking Celebrity Break-Ups

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Celebrity romances come and go so often, it's hard to get really attached to Hollywood couples. But who are we kidding, we're suckers for certain ones, so when relationships crumble for our favorite stars, it makes the room a little dusty sometimes.

With a Sandra Bullock-Jesse James divorce likely looming and ready to join the ranks of the most painful celebrity break-ups, here's a look at 10 that hit us hard:

Timberlake and Biel Photo

10. Taylor Swift and Taylor Lautner. Okay, they were barely a couple ... and may still be. But this split rocked us to the core ... we really wanted it to work.

9. Lindsay Lohan and Samantha Ronson. Is Lindsay going to die? Is she going to return to men? Will they ever stop feuding on Twitter? We cannot deal.

8. Denise Richards and Charlie Sheen. The split of these two stars? Not wholly unexpected, given that it's Charlie Sheen. But it was still scandalous and sad.

7. Reese Witherspoon and Ryan Phillippe. Two sweet kids, seven years of marriage, always seen smiling and laughing together. All a facade, apparently.

6. Tom Cruise and Nicole Kidman. Before Katie Holmes, Cryise was married to Nicole for 10 years and had adopted two children before splitting up in 2001.

Those were the good ol' days ...

5. Nick Lachey and Jessica Simpson. Before she was sexual napalm and starring on low-rate reality shows, she was younger, hotter, married sexual napalm starring in higher-rate relative shows and also producing hit pop songs. Ah, 2004...

4. Britney Spears and Justin Timberlake. Admit it, how hard were you rooting for them to get married? Admit it ... how hard are you still rooting for that?!

3. Jon and Kate Gosselin. When seemingly harmless reality TV couples go haywire and become far bigger stars based on the celebrity gossip they generate.

2. Sandra Bullock and Jesse James. We're also sticking a fork in this one because she can't possibly take him back... right? The Oscar-winner and the bad boy seemed to be a uniquely wonderful fit ... until along came Michelle "Bombshell" McGee.

1. Brad Pitt and Jennifer Aniston. The ultimate Hollywood fairy tale couple had it all. A-list TV and film success, reeediculous good looks and a happy home life. Hearts shattered around the world when Brad and America's sweetheart split.

When and if they split, Jesse and Sandra will be up there with Brad and Jen on our list of most memorable, painful celebrity break-ups. Which one were you saddest about?

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i honestly think that victoria justice and avan jogia should date and then break up!!!!!!!!!!! aaaaaahhhhhh saddest break up eva!!

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Yup..d breakup of Tom and Nicole was totally unexpected and shocking..they were so perfect.

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Elin has Not taken Tiger back,I believe that she has given him a home base,so that he can peacefully return to golf.

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When Brittany and Justin broke up, she lost her innocense.

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geez, why do people get married in the first place? Love is RARELY intended to last a lifetime. Its a gamble you take, and there are no guarantees. Hearts get severely broken, its all chaos and turmoil...just follow george clooney....single and having fun..great!

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WHOOPIE!
1/2 OF MARRIAGES FAIL!
IT'S MORE ENTERTAINING FOR THEM TO BREAK-UP!

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what about tiger and elin? oh ya, that pathetic waste took him back