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that's the way the cookie crumbles 

Oh, I'm sorry your girlfriend broke up with you; I guess that's the way the cookie crumbles.

that's the way the cookie crumbles 

Bruce Almighty, said by Bruce Campbell in an effort to make a catchphrase similar to "And Thats the way it was"

Also a pun in that film, as the news story was about a giant cookie,

It means:

Thats the way it happened
....*news story*..

and thats the way the cookie crumbled

that's the way the cookie crumbles 

Timmy: I can't believe I revised for four hours on those topics and not one of them came up in the exam
Jinny: That's the way the cookie crumbles
Timmy: stfu

that's the way the cookie crumbles 

It means that's how life is. It's used after something unfortunate happens
Jim knocks over Jane's ceramin doll collection and says "Well that's the way cookie crumbles"

that's the way the cookie crumbles 

When something doesn't go your way.
Dude: Bummer, my girl left me.
Other Dude: That's the way the cookie crumbles...

that's the way the cookie crumbles 

Jake went to prison. Oh well, guess that's the way the cookie crumbles.