Said in response to some ones sob story. Shortened from the full statement of "Cry me a river, build a bridge and GET THE FUCK OVER IT!"
Very old saying predating any Justin Timberflake warbles or other pop culture references. Interestingly still in common use today.
Whinger: My cars broken down and Im poor and I lost my job and my wife left me and when she left, she ran over my dog.
Cold Hard Bastard: Cry me a river buddy, cry me a river.