Cassie Ramone of Vivian Girls/The Babies
The Carpenters, “Another Song”: I really like the metaphors in this song comparing a breakup to the sun rising at dawn. Dawn is a very harsh time even though it's supposed to be beautiful. I also like how the intro is almost overly prissy and by the end of the song they're in a weird, kind of heavy psychedelic jam.
Moshe Rozenberg of DD/MM/YYYY
The Mothers of Invention, “How Could I Be Such A Fool?”
John Edelstein of Fiasco/Bluffing
Eskemo, “Riding”: It's able to be concise without sacrificing any emotional power or getting too wordy. It's deceptively challenging to write a song so simple yet effective, in terms of both music and lyrics. Runners up would be “Ex-Factor” by Lauryn Hill or “You're Breakin' My Heart” by Harry Nilsson.
Bruce Willen of Double Dagger
Sebadoh, “…Burned (Everybody's Been Burned)”: Sebadoh has so many great break up songs (Sister, Soul and Fire, Vampire) that I had trouble picking just one. But this cover of a Byrds song is perfect for soaking in one's own misery.
Doug Tuttle of MMOSS
The Byrds' “Time Between” into “Everybody's Been Burned”: The most devastating pair of songs I've ever heard back to back on a record. First “Time Between”, a Chris Hillman tune about a failing long distance relationship, then “Everybody's Been Burned”, a Croz song about wanting to give up on love all together. Such sad songs, the rest of the record had to be about aliens and what it's like being a rock star.
RPR of Keep Shelly In Athens
Soft Cell, “Say Hello, Wave Goodbye”: “…because it is such an honest and at the same time gentle way to say goodbye Just smile and say hello, Say hello then wave goodbye. Every time I listen to it, I want to break up for the sake of this wonderful song.”
Jason Hendardy of Permanent Collection
The Zounds, “True Love”: This song seemed like a good candidate for the opener for a favorite break up songs list because I mean “true love, what's it really all about”? Plus it's a good up beat first song.
Morrissey, “I Don't Mind If You Forget Me”: What's a breakup mix without the sultan of sad? This was kind of mandatory. I like to think that one can debate that metaphorically the guitar noodling on this song is pretty resemblant of how obnoxious people can be.
Karen Dalton, “Reason to Believe”: Close it all out with a stripped down song. This song can speak for itself.