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Let’s face it, Valentine’s Day is the WORST holiday of the year! We launched this playlist series back in 2015 as a way of getting through that awful day, February the 14th. We are pleased to bring you Vol. IX which may be the most upbeat musically of any installment in the series thus far. It even starts off with two songs about the silver lining that can sometimes come with a breakup.

Thanks to all of our artists who took the time to contribute their picks from the vast catalog of break-up songs / songs about heartache – they all dug deep this year and really came through with some choice cuts:

1. Teenage Fanclub – “Free Again”
Selected by Daniel Gill of Force Field PR

“A cover of Alex Chilton, TFC made it even more power pop and upbeat, celebrating the feeling of newfound freedom after a breakup (the silver lining).”

2. The Cry – “Starting Again”
Selected by Sean of S.C.A.B.

“People rarely see a breakup as a chance for renewal. The end of a relationship can provide an enormous well of growth and healing for those involved. It can be a source of joy if you’re capable to shift your lens. Starting Again captures that feeling of exciting renewal.”

3.. XTC – “That’s Really Super, Supergirl”
Selected by Stephen Steen of Megadose

It’s an I-got-burned-by-you-but-good-riddance song. Also has one of my favorite guitar solos from them. Good stuff!”

4. Vashti Bunyan – “Don’t Believe”
Selected by Elyse of Blues Lawyer

5. The Raveonettes – “Love In A Trashcan”
Selected by Widows Gold

6. Strawberry Switchblade – “Deep Water”
Selected by Frankie Rose

7. Florry – “When I Kicked You Out of The Band (I Wasn’t Kicking You Out of My Life)”
Selected by Kip Berman of The Natvral

This is a breakup song of a sort, but there’s an acknowledgment that even as one intimate relationship ends, another ought to remain. Don’t throw your baby out with the bath water.”

8. Sparks – “I Married Myself”
Selected by Oliver Marson

“I went for Sparks as they’re probably one of my biggest influences. This one, like all of their songs, is hilarious. It’s sort of about reveling in being lonely. As ever it’s very tongue in cheek.”

9. The Beach Boys – “Tears In The Morning”
Selected by Tree of Peaceful Faces

“A heartfelt and bitter breakup song from the underrated early ‘70s featuring vocals and songwriting from the underrated Bruce Johnston”

10. Broken Social Scene – “Anthems For A Seventeen Year-Old Girl”
Selected by Sara Noelle

“This tune has always captured that feeling of heartbreak & angst so well — something about the repetition of the lyrics: “Used to be one of the rotten ones and I liked you for that…”

11. John Cale – “I’m Not The Loving Kind”
Selected by Tomten

12. Jonathan Richman – “True Love Is Not Nice”
Selected by Beat Awfuls

13. Medium Build – “Give It Like You Used To”
Selected by foamboy

14. The Rising Storm – “A Message To Pretty”
Selected by Maraschino

15. Blonde Redhead – “Misery Is A Butterfly”
Selected by Franklin Gothic

“It’s pretty lovey lovey, but also like extremely spiteful. “With her small ugly face” – I love it.”

16. The Primitives – “Laughing Up My Sleeve”
Selected by The Umbrellas

17. Sure Sure – “Spirit Mission”
Selected by foamboy

18. The Only Ones – “Oh Lucinda (Love Becomes A Habit)”
Selected by Elyse of Blues Lawyer

19. New Order – “Guilty Partner”
Selected by Frankie Rose

20. Mary Lou Lord – “I Figured You Out”
Selected by Rob of Blues Lawyer

21. Shop Assistants – “I Don’t Wanna Be Friends With You”
Selected by Chime School

22. Karen Dalton – “Sweet Substitute”
Selected by Lindsay Clark

23. Elliott Smith – “Drive All Over Town”
Selected by Kisskadee

24. The Letters – “Nobody Loves Me”
Selected by The Umbrellas

25. Dan Penn – “Nobody’s Fool”
Selected by Photo Ops

26. Paul Simon – “Some Folks’ Lives Roll Easy”
Selected by Waldo Witt

“One of my favorite tracks off one of the best breakup albums ever”

27. Björk – “Unravel”
Selected by Rusty Santos

28. Medicine – “Never Click”
Selected by Taleen Kali

29. Hüsker Dü – “Standing In The Rain”
Selected by The Umbrellas

30. TiaCorine – “Lotto”
Selected by The Narcotix

“This song is anti-love and anti-commitment. It is pro-sex and pro-violence. In TiaCorine’s universe, men don’t stay the night. “Can’t hold me, cuz i get money on my lonely” is truly the opposite of Valentine’s Day.”

31. Liz Phair – “Fuck and Run”
Selected by Marion of Fatal Jamz

32. Jed Arbour – “Never Got Off”
Selected by Alexis Castrogiovanni

33. Lorde – “Supercut”
Selected by Puppy Angst