Last month, EW's Jason Adams put up a post on the Music Mix asking "What's the most heartbreaking song of all time?" and naming Smog's "Cold Blooded Old Times" as his top pick. Nearly 2,000 comments later, we realized we'd touched a (really depressed) nerve. So we sat down to create a list of our own favorites, available below in reverse order, No. 50 to No. 1.

The list begins with the lamentations of one George Michael, and travels through to... well, we won't spoil it. But you should head over to http://music-mix.ew.com/heartbreak to experience the full extent of our pain, and feel free to accompany your journey with the imeem playlist of all 50 songs we've posted here. (You can embed that on your own site, should you wish to share it with your friends and weepy loved ones.) And finally, of course, the comments section at EW.com is open so you can let us know where we got it right, where we went wrong, and what we left off. But be gentle. We're sort of in a fragile place right now.