When they finished writing it, co-author and country music legend Bill Anderson told Jon Randall "that's the saddest song I ever heard, nobody will want to listen to it". I guess somebody did. When Brad Paisley and Alison Krause recorded "Whiskey Lullaby" it went to #2 and won song of the year. They were good, but hearing the phenomenally talented Randall sing it with his wife Jessi Alexander at a tribute to Anderson is as good, and as sad, as it gets.
In a genre where sad songs are woven into the fabric of the art, Whiskey Lullaby stands alone. You should not listen to this song drunk. Or perhaps you should only listen to it drunk. Either way, if this one doesn't make you cry, nothing will.