The Sis and I were chatting online when, out of nowhere, she unleashed the prompt, "Ok, so saddest songs ever." We then began to list our favorite sad songs, going back and forth until I left work for the night. I tossed out a few off the top of my head and then checked my phone for more suggestions. This is what she and I came up with on the fly:Me "Lost Cause," Beck "Crying," Roy Orbison "Are You Still in Love With Me?", Tift Merritt "Hallelujah," Jeff Buckley "He Stopped Loving Her Today," George Jones "Houses on the Hill," Whiskeytown "Martha," Tom Waits "Winona," "Nothing Lasts," "Your Sweet Voice," "Everything Changes," "I Almost Forgot," Matthew Sweet "Steven," Denison Witmer "Far, Far Away," Wilco "I Should Have Been True," The Mavericks "Oh My Sweet Carolina," "La Cienega Just Smiled," "September," Ryan Adams "Please Tell My Brother," Golden Smog "Salome," Old 97's "Travelin' Soldier," "Without You," Dixie Chicks "The Stars Above and My Heart in Your Hands," Christopher Denny (to which I attached the caveat that it's so sad I can only listen to it every couple of months) "Sweetest Waste of Time," Kasey Chambers and Shane Nicholson "I'm So Lonesome I Could Cry," Hank Williams "Broke, Lovesick, & Driftin'," Hank Williams III "Always On My Mind," Willie Nelson "Please Break My Heart," Caitlin Cary and Thad Cockrell The Sis "Fred Jones," Ben Folds "Casimir Pulaski Day," Sufjan Stevens "The Lonely 1," Wilco "Your Long Journey," Robert Plant and Allison Krauss "Mad World," Gary Jules "The Blower's Daugter," "Amie," Damien Rice "She's Got You," "Crazy," "Walkin' After Midnight," Patsy Cline "A Ghost in This House," Allison Krauss and Union Station And that's just the stuff we came up with while bored at our respective jobs. We didn't have iTunes libraries or stacks of CDs to check. I think we came up with some respectable titles, and I'd like to hear suggestions for more. Any genre, any era. Just hit me with the sadness and we'll come up with the best damn wrist-cutting, whisky-sipping playlist anyone's ever seen. Fire away.