Selections from Heavenly, Rocketship, Frankie Rose, Peel Dream Magazine, Jeanines, Lightheaded, LAKE, Gold Star, Color Green, Rusty Santos, Silk Daisys, moondaddy, LARGE, Van Chamberlain, Swimming Bell, Photo Ops and more!
Listen to the playlist on:

As we always say, 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. Each year, we ask artists we work with for their suggestions for a playlist about heartache, and they never fail to deliver. We are pleased to bring you Vol. XII – crazy to think we’ve been doing this for twelve years now with hardly any tracks repeated (feel free to fact check us on that!).
Last year, something happened that hadn’t happened before: two of the artists we invited to contribute to the playlist picked songs by Hüsker Dü (luckily they were two different songs). Well, this year the double picks from the same artist were even more out of control, with two songs each from Tom Petty, Cat Power, The Cure, Lucinda Williams and……Strawberry Switchblade? Once again, everyone still picked different songs, even if there was a strange alignment in culling from those five artists’ catalogs for heartache.
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:
1. Shop Assistants – “I Don’t Wanna Be Friends With You”
Selected by Papa Slumber
2. Solange – “Losing You”
Selected by LARGE
3. Would-Be-Goods – “Don’t Come Crying to Me”
Selected by Heavenly
4. The 6ths – “You Can’t Break A Broken Heart”
Selected by Daniel Gill (Force Field)
5. Wilco – “I Am Trying to Break Your Heart”
Selected by Peel Dream Magazine
“Masterpiece. Perfect band perfect album.”
6. Little Eva – “Breaking up Is Hard to Do”
Selected by Lightheaded
7. Yura Yura Teikoku – “空洞です”
Selected by Julie Hill
8. The Cure – “Winter”
Selected by Silk Daisys
“This is the most melancholy type of breakup song—it sounds like rambling alone through a dead forest before a storm and popping your collar against the wind, tortured by thoughts of a long lost love, fully aware of how dramatic you’re being but too lost in your beautiful sadness to care. Soundtrack for an Edgar Allen Poe story.”
9. Tom Petty and the Heartbreakers – “Fooled Again (I Don’t Like It)”
Selected by Gold Star
10. Cat Power – “Good Woman”
Selected by Sara Noelle
“A beautifully sad song from one of my favorite records”
11. Bee Gees – “Love So Right”
Selected by Rocketship
“Another perfect break-up song from the masters of melancholy pop. For that certain someone.”
12. Jeff Buckley – “Morning Theft”
Selected by moondaddy
13. Richard Thompson – “Reckless Kind”
Selected by LAKE
14. Arthur Russell – “I Never Get Lonesome”
Selected by Color Green
15. The Beach Boys – “Angel Come Home”
Selected by Photo Ops
16. Ride – “Portland Rocks”
Selected by bloom effect
“‘Portland Rocks’ has that intense feeling of standing at the edge of the world, where love feels already slipping away. A classic breakup sentiment.”
17. PJ Harvey & Thom Yorke – “This Mess We’re In”
Selected by moondaddy
18. Strawberry Switchblade – “Go Away”
Selected by Silk Daisys
“A song about abandonment that sounds like being abandoned on a dreary English cliffside. So goth and emotional, a perfect vibe for looking out a rainy window and letting the eyeliner roll down your cheeks.”
19. Weezer – “The World Has Turned And Left Me Here”
Selected by LARGE
20. John Lennon – “Jealous Guy”
Selected by LARGE
21. Timi Yuro – “What’s A Matter Baby (Is It Hurting You)”
Selected by Jeanines
22. The Only Ones – “Out There In The Night”
Selected by Heavenly
23. Robert Wyatt – “Memories Of You”
Selected by Color Green
24. Anthony Hamilton – “I’m A Mess”
Selected by Daniel Kleederman
“All i have to say is that it goes all the way there. I have memories of just loving this song and production as a teenager but not really understanding the song, of course, until later in my life.”
25. Los Ángeles Azules – “Cómo Te Voy A Olvidar”
Selected by Rusty Santos
“One of the most beautiful songs about longing for true love that still exists after separation.”
26. Lucinda Williams – “Still I Long For Your Kiss”
Selected by Gold Star
27. Silver Jews – “Pretty Eyes”
Selected by Color Green
28. Beck – “Lost Cause”
Selected by Swimming Bell
“From the best break-up album of all time, in my opinion”
29. Irma Thomas – Medley: “Coming From Behind/Wish Someone Would Care”
Selected by Color Green
30. Annie Lennox – “Walking on Broken Glass”
Selected by Van Chamberlain
“This song is one of those uplifting-i’m-moving-on-from-
31. Tom Petty – “Time To Move On”
Selected by Van Chamberlain
“One of those perfect break up songs that immediately centers you back into your own life’s story. Feels good. We need that. “Which way to love land?
Which way to something better?
Which way to forgiveness?
Which way do I go?”
32. Sippie Wallace – “Women Be Wise”
Selected by Rusty Santos
“I’ve loved this song most of my life; the premise is so human and sinister.”
33. Buzzcocks – “Ever Fallen in Love (With Someone You Shouldn’t’ve?)”
Selected by Rusty Santos
“I think this was the first time I realized you could have a punk song about love as long as it had caustic intent.”
34. Ozuna – “El Farsante”
Selected by Rusty Santos
“This song taught me that break-up songs hit a lot harder in Spanish. I remember being in a recording studio in China listening to this super loud, I didn’t even have to understand all the lyrics to know what it’s about.”
35. The Stone Roses – “I Wanna Be Adored”
Selected by Paper Pools
36. The Cure – “Disintegration”
Selected by Paper Pools
37. Veronica Falls – “Found Love in a Graveyard”
Selected by Silk Daisys
“A masterpiece of songwriting…it takes you on a journey to another world and back. Veronica Falls is an obsession—I’ve been playing their 2 albums nonstop the past couple years. Their punk rhythms mixed with 60s jangle/harmonies—and canticle melodies that are so airy and ethereal but with these playfully dark, sardonic lyrics—strike a perfect balance. It’s like the Pixies covering the Byrds with lyrics by The Smiths. They’re so incredibly underrated.”
38. Cat Power – “Metal Heart”
Selected by moondaddy
39. Lucinda Williams – “Save Yourself”
Selected by moondaddy
40. Chris Bell – “Make A Scene”
Selected by moondaddy
41. Jets To Brazil – “Starry Configurations”
Selected by Sweet Nobody
42. Cathy Dennis – “Too Many Walls”
Selected by Silk Daisys
“I’ve loved this song since I was a kid. I think Delilah played it a lot on her show? I’d just sit in the back of the car while my parents drove around at night with the radio on, and I’d wonder about the cruel world that would separate this woman and her perfect love.”
43. Strawberry Switchblade – “Trees and Flowers”
Selected by Van Chamberlain
“The sweetest sounding sentiment of misery one might find comfort in this Valentine’s Day.
‘For I hate the trees
And I hate the flowers And I hate the buildings
And the way they tower over me
Can’t you see?
I get so frightened
No one else seems frightened
Only me, only me'”
44. Dizzee Rascal – “I Luv U”
Selected by Rusty Santos
45. Coil – “Going Up”
Selected by Frankie Rose
46. Go Sailor – “I’m Still Crying”
Selected by Jeanines