In honor of the upcoming holiday, I thought I’d put together a little playlist. This isn’t your typical V-day playlist, though, because it was inspired by the song “My Funny Valentine,” a song I absolutely loathe. It’s a standard, but it’s just awful, and mean, and it’s the worst so-called “romantic” song in the history of romantic songs (although I would argue that there’s some pretty stiff competition for that spot in the following playlist): “Here, let me catalogue all your faults as I see them, set them to music, and then, once I’ve torn you down, reassure you that I love you despite all your physical and personality grotesquerie.” One has no choice but to swoon, no?
So this list is a list of songs that illustrate bad, unhealthy, love in its myriad forms. It started at 96 songs, and I narrowed it down to 33; that was the best I could do. What can I say? People write a lot of songs about some messed up relationships.
Anthony-Nickel Creek: It’s only a lot creepy when someone tells you that it’s not going to happen for the two of you, and you insist that they’re wrong and they will love you, if only through the sheer force of your will.
The Boy Who Never-Landon Pigg: I think this is one of the sadder songs on the list, in that it’s about a someone who is so terrified of a broken heart, or broken dreams, that he never even tries. The “sour grapes” approach to love is, in my opinion, no less painful than to love and lose; it’s just a different flavor of pain.
Breakfast in Bed-Nicole Kea: Originally sung by Dusty Springfield, here we have infidelity, a man who goes back to his ex for solace when it isn’t working out with his current, and she lets him. If they’re so good together, they should just get back together, assuming they can’t work out some kind of ethical arrangement between the three of them.
My Funny Valentine-Sarah Vaughan: Discussed above. I will never understand why this has been covered by so many. It’s mean, and the music is sad.
Cruel to Be Kind-Nick Lowe: People who treat you badly do not love you. Period. There’s no use trying to understand them; RUN!
Won’t U Please B Nice-Nellie McKay: I particularly dig the jaunty tune underlying truly menacing lyrics. The most sweetly delivered collection of nasty threats ever offered to a beau.
I Wish It Was Over-Teddy Thompson: You know you’re in a bad situation when you fantasize about it being over. Do everyone a favor and move on.
Something to Fall Back On-Todd “the god” Rundgren: The heartbreak of waiting around for someone to appreciate you the way you appreciate them is a poignant, and quite possibly universal, one.
Give Judy My Notice-Ben Folds: Never settle; and never be the one settled for; thin love ain’t love at all.
Break Your Heart-Barenaked Ladies: Better to hurt someone honestly, than to lie and hurt them worse down the road. Communication is ultimately good.
Poison & Wine-The Civil Wars: The Civil Wars said they wrote this song as a conversation between a couple of things that they would never say, but felt nonetheless. This couple loves each other but has fallen out of love and is lost. “I don’t love you and I always will.” Anyone who’s gone through a really rough patch in a long-term relationship will relate to that lyric, I think.
As Cool As I Am-Dar Williams: She’s dating a manipulative jerk who wants to poke at the insecurities he assumes she must have, and when he behaves rudely, he’s fully prepared to make it her fault if she gripes. Nice. There is a happy ending to this song, though, because she totally sees through his bullshit.
The Man Who Stole a Leopard-Duran Duran: Man-animal love: It’s not just for Superbowl ads.
David Duchovny-Bree Sharp: Celebrity fantasy, or prelude to a stalking? It’s the finest of lines.
Indian Lover-Jude: This fucking song…abusively entitled, possessive, homicidal, misogynist, and racist to boot, all told through a gorgeous vocal that kills me every time I hear it. I hate Jude for that; if this song weren’t so vile, I’d cover it and play it at every gig. Instead, I listen to it in the privacy of my own home, sing it loudly when alone in my car, and wash my mouth out with soap when I’m done.
If You Hadn’t But You Did-Kristin Chenoweth: Incorrigible cheater receives vigilante justice. Relationship of the year here.
Thin Line Between Love and Hate-The Pretenders: The last of the “homicidal lover” songs in this mix. Still waters run deep, as they say.
That’s the Way I Always Heard It Should Be-Carly Simon: With this song, we move into the marital ennui section of the playlist. People who are still nominally together, but haven’t been emotionally and spiritually together for years. No wonder Carly was scared; and as it didn’t work out with James Taylor, I guess she wasn’t wrong. I always felt that the end of the song indicated resignation to that particular path, rather than hopeful optimism and a change of heart.
Kinder Blues-Maia Sharp-A song about how sometimes love isn’t enough, that hard times and too much compromise can do love in. Not being horrible is not the same as it being good.
The Bed Song-Amanda Palmer & the Grand Theft Orchestra: The opposite of the previous song, they were so in love when they were young and poor; the “better” their outer life got, the further apart they got from each other.
The Kind of Love You Never Recover From-Christine Lavin: Two people with lifelong love…just not with each other. What a waste.
Why Can’t He Be You-Patsy Cline: I think it’s totally uncool to be in a relationship with someone you don’t really love because it’s better than being alone; they deserve someone who adores them. And if you can’t appreciate someone who’s good for and to you, pining instead for the one who dumped you, then you’ve got some internal work to do.
I Married Her Just Because She Looks Like You-Lyle Lovett: The flip-side of the previous song.
China-Tori Amos: There is nothing lonelier than feeling alone while sitting next to the one you love.
Need You Now-Lady Antebellum: An ode to ill-advised drunk-dialing (as if there’s any other kind).
The Dark End of the Street-The Commitments: Cheating is so romantic. Find the courage, be honest, and see what happens.
Dixie Boy-April Smith and the Great Picture Show: Once and for all—if your partner strays, it ain’t the fault of the person they stray with. I will never understand blaming and hating the person your partner cheats with; I guess it’s easier than accepting that the person you’re dating is an asshole. I particularly like the line “I can be a bitch when it comes to my stuff.” Oooookay…because you you classify another human being as “my stuff”? That’s healthy!
My Boyfriend’s Back-The Angels: So much wrong with this song. A guy who won’t take no for an answer, and spreads nasty rumors. A girl who wants her boyfriend to beat him up for it. I absolutely believe that people have the right to politely express their romantic interest in other human beings, but with that comes the concomitant responsibility to graciously accept a polite “no” and walk away, the first time.
Keep Young and Beautiful-Emmy Rossum: Because as women, it is our responsibility to be hot (by a constantly shifting, individually arbitrary standard) from the time we’re 11 until we’re in the grave, or nobody’s gonna love us nohow, and that’s what we deserve. Not to mention that we should be good consumers of all the crap they want to sell us after they exploit our insecurities. This is an old, old song from the ’20s, but while the message is not quite so overt these days, it’s steadfast as ever.
Wicked Way-Ben Taylor: Ben is the son of the aforementioned Carly Simon and James Taylor. I guess we should give him points for honesty of intention, though demerits for rapey-ness of getting a girl drunk so he can screw her without enthusiastic consent.
Lover I Don’t Have to Love-TFDI (Tony Lucca, Matt Duke, & Jay Nash): This is a cover of a Bright Eyes (Conor Oberst) song, but I think the cover is superior.
Without You-Nilsson: Whenever I think of Harry Nilsson, I am reminded of an interview with The Beatles where they were asked what they were listening to, and they all namechecked Nilsson (if you think you don’t know him, he’s the guy who sang “You put the lime in the coconut and drink it all up”). The BEATLES, y’all. He hung out with John Lennon when John left Yoko for an 18-month “lost weekend.”) He was all over the place musically, but it was all good. Heartbreak sucks, but I assure you, you CAN live without someone. If you really can’t, you should seek professional help immediately if not sooner.
Can’t Smile Without You-Barry Manilow: Bringing it home with Barry, because it doesn’t get more co-dependent than this song.