When you need it: If you think your heartbreak story is sad, just go ahead and take “The Window Up Above” for a spin. It’s the story of a husband who desperately loves his wife and is constantly watching her cheat on him and talk shit about their marriage.. Yep, life’s not so bad after all.
Most potent lyrics: “I heard you whisper to him softly that our marriage was all wrong. But I hope he makes you happy, and you will never lose his love”
When you need it: In the moment when you’re drowning in guilt over the terrible things you’ve done, guilt, and self-pity, this latter-day George Jones song will come around to shake your shoulders, look you in the eye, and tell you you’re completely right to hate yourself because you really are incredibly selfish. Just kidding: this song is really for the people who are effed over by the selfish bastards among us. Listen to it and pretend that it could sing some sense into them.
Most potent lyrics: “There is a woman we both know, I think you know the one I mean. She gave her heart and soul to you, you gave her only broken dreams.”
When you need it: When you’re ‘accidentally’ walking by your ex-person’s apartment or your unrequited crush’s favorite bar, this song will power your steps with the power of empathy. Possum’s got your back when everyone else is calling you a stalker.
Most potent lyrics: “Just because I haunt the same old places where the mem’ry of her lingers everywhere, just because I’m not the happy guy I used to be, she thinks I still care.”
When you need it: This is just an incredibly beautiful, simple love song, but Possum’s voice is so inherently soaked with melancholy that you won’t be able to help imagining the end of it all as you spin this one on the record player during your necking session.
Most potent lyrics: “Take me to your most barren desert, a thousand miles from the nearest sea. The very moment I saw your smile, it would be like heaven to me.”
When you need it: This song is ostensibly a manifesto for the perpetually heartbroken and hung-up (aka humanity) to go ahead and stop the cycle of self-pity, get up and “keep smiling.” It’s downright cheery as far as George Jones goes. Administer this song three times a day when you’re truly ready to move on for painless results.
Most potent lyrics: “My tears were scattered with all was shattered.”
When you need it: Whenever you’re in looooooooooooove and you’re never going to drink or cry again, this song will be there. Then, later, when that ends in sadness and devastation and you want to remember the good times, this song will be there.
Most potent lyrics: “Baby, You’re as smooth as Tennessee whiskey, you’re as sweet as strawberry wine, you’re as warm as a glass of brandy, and I stay stoned on your love all the time.”
When you need it: “Just One More” is the best friend a sad drunk ever had. It’s not just about drinking your pain away, it also sounds just like the head nodding off, tears you didn’t intend, closing time before you know it kind of breakup drunk that everyone must endure at least once in life. George understands, obviously.
Most potent lyrics: “Put the bottle on the table, let it stay there till I’m not able to see your face in ev’ry place that I go.”
When You Need It: When you’re the one who messed up (“when you’re caught cheating twice”), you still need to drown yourself in whiskey and self-pity. Possum is here for that, and for you. His love and empathy in unconditional.
Most potent lyrics: “And the ocean of liquor I drank to forget her is gonna kill me but I’ll drink ‘til then.”
When you need it: The perfect tune to accompany that terrifying moment when you realize that your identity is now inextricably tied to some other fallible human heart, and now there’s no telling what will happen to you.
Most potent lyrics: “Have you ever looked up at a sky with no blue? Then you’ve seen a picture of me without you.”
When you need it: George will be there for you for the night after your huge breakup when you get a little too drunk, and none of your friends are awake to cry to. You may find yourself listening to this song so many times that night that you’ll never be able to hear it again without having pavlovian heartache, but it’s the only thing that will get you through.
Most potent lyrics: “I’m goin’ honky tonkin’, get as tight as I can, and maybe by then you’ll ‘preciate a good man”
When you need it: Haven’t had a good cry in awhile? Get this song ready, get into a room by yourself, and let it out. You might think you’ve heard it enough times that you must be immune by now, but you’re wrong. This song, given your full attention, is like the musical equivalent of the love story in Up – if tears don’t at least start springing up behind your eyeballs, you might want to check your pulse.
When you need it: Whenever you need a kick in the old gut, this song will be there for you. It is, for one thing, just an excellent example of storytelling by legendary songwriter Jerry Chesnut. The device of a stoic heartbroken divorcee talking about a “good year for the roses” instead of his actual feelings is so dad-like and sad-like that it will hurt you so good.
Most potent lyrics: “After three full years of marriage, it’s the first time that you haven’t made the bed.”
When you need it: If you ever start thinking that maybe all this wallowing in sad bastard/ette music isn’t so good for your soul, put “The Grand Tour” on for a perfect melodic reminder of how beautiful sadness sounds.
Most potent lyrics: “As you leave you’ll see the nursery, oh she left me without mercy, taking nothing but our baby and my heart.”