Love bites, depressing songs about love, break up songs
Damian Kulash

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If you are expecting to be alone this Valentine’s Day, or even if you just hate everything the holiday stands for, then this mix is for you. It contains songs that are anti-love, including some that are downright hateful. And even if you’re happily married or attached, you’ll find this mix amusing.

“Love Is a Losing Game,” Amy Winehouse (Back to Black)
Hopefully Amy Winehouse doesn’t overdose before she makes more music, because her second album is a real gem, including this really, really depressing song.

“Fools In Love,” Joe Jackson (Look Sharp!)
I don’t know if Joe Jackson is still as pissed as he was when he wrote this song. Either way, not only are the lyrics brilliantly bitter, but the lounge-y piano is the perfect backdrop.

“No More ‘I Love Yous’,” the Lover Speaks
(The Lover Speaks)

This band had exactly one album before it ran out of ideas. I mean, the whole premise of this ‘80s synth-new wave band was based on love songs.  But they delivered a really great batch of songs that you may not have heard, except for the Annie Lennox cover of this one.

“Love Sucks,” Nathan Angelo (Through Playing Me)
This one needs no explanation, though the track is surprisingly upbeat. And Angelo is a young Gavin DeGraw type with a load of potential.

“Love Hurts,” Nazareth (Hair of the Dog)
You ever notice no cover bands ever attempt this song? That’s because Dan McCafferty is one of the most underrated singers in rock history, and if you guys tried to sing like him you’d likely bust a nut.

Isn’t Love My Friend?” Todd Thibaud
(Northern Skies)

Mr. Thibaud sounds so much like Glen Phillips of Toad the Wet Sprocket, you might actually think this IS Phillips. But it’s not, and this achingly sad mid-tempo rocker is one of Thibaud’s best.

“Take the L,” The Motels (All Four One)
This is one of those lyrical ideas I wish I had come up with myself: “Take the L out of lover / And it’s over.” Simple, poetic, and perfect for this mix.

“Katie,” David Ford (I Sincerely Apologise for All the Trouble I've Caused)
Here is a British bitter man if there ever was one. Check out these lyrics: “Katie / Will you say to me / Will you just please tell me what the fuck is going on?” Honestly, this is a brilliantly brooding album, but it wears on you after about five listens.

“I’ll Get By,” Eddie Money (Right Here)
For my money, this is one of the greatest breakup songs of all time. Not only does it have the lyrics, but the piano balladry just captures the whole mood.

“Let It Die,” Feist (Let It Die)
This is another stunning, stunning breakup song. Dig it: “Let It Die / Get out of my mind / We don’t see eye to eye / Or hear ear to ear.” And Ms. Feist has the perfect voice to deliver this bit of bad news.

“Maybe It’s Me,” Ingram Hill (June’s Picture Show)
This is another one of those songs that really make you feel the ache of breakup. Even the guitar parts sound sad.

“Here Come Those Tears Again,” Jackson Browne (The Pretender)
Once again, we’ll let the singer and songwriter tell it better than I can: “Here come those tears again / Just when I was getting over you / Just when I was gonna make it through / Another night without missing you.” Ah yes, beautiful heartbreak in a song.

“B.M.F.A.,” Martha Wainwright (Martha Wainwright)
A really pretty sad song, until Ms. Wainwright lets you know what the abbreviation stands for: “Bloody Mother Fucking Asshole.” Yeah, take that. (Ed.’s Note: This song is actually about Wainwright’s father. Yikes!)

“Someday We’ll Know,” New Radicals (Maybe You’ve Been Brainwashed Too)
This is a truly incredible song about realizing the hard truth that you’ll never, ever be with the love of your life.

“Photograph,” Ringo Starr (Ringo)
Maybe this track is too bouncy to be sad, but lyrically it’s a song that really details the whole ordeal of breaking up in vivid fashion.

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