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Sad Ass Songs: Emily Skillings

Sad Ass Songs: Emily Skillings

Sad Ass Songs is a weekly column where I ask some of my favorite writers to tell me about their favorite sad songs. They send me songs and then I send them questions and then I post their answers here and then we all cry a little bit.

This week I talked with Emily Skillings, the author of many good chapbooks, such as Backchannel (Poor Claudia) and Linnaeus: The 26 Sexual Practices of Plants (No, Dear).

The Song: “In The Evening (It’s So Hard to Tell Who’s Going to Love You the Best” by Karen Dalton

MC: I’m so happy you picked Karen Dalton, because Karen Dalton is the fucking queen. Why is Karen Dalton the fucking queen?

Karen Dalton is more of a duchess? Or a field witch? Sulky lady-in-waiting? There’s just something about her squawking. It gets in you know? It grinds its way. I’m very attracted to voices that are on the verge of a break–I’m thinking Rickie Lee Jones here too–and I remember the first song I ever heard by her was “Something on Your Mind.” There’s this plodding, thrummy instrumental intro and then she breaks in and sings “yesssssssterdaaaaaaaaay…” in the ugliest and most abrupt way possible. It’s almost funny.

Dalton is very good at playing the space between emotional registers, which I guess is where I do most of my time. I might argue that Dalton’s songs are lest pained than they are anxious. Her anxiety seems to be specifically about place/placelessness, how New York treats her, her mistrust of it, her rural origins.

i.e. “Even the thought of New York was going insane,” from “Same Old Man”


“Do you feel like something’s not real?/ Let the Spirit move you again/ Are you leaving for the country?/ You say the city brings you down/ Leave the iron cloud behind and feel the circus moving on” from “Are You Leaving for the Country?”.

There’s often a vague threat of packing up and leaving. There’s a lot of that in this song too. I think most New Yorkers feel this from time to time, and she’s good at isolating that moment when you recognize that you are being deceived by the false spirit of a place.

MC: What’s your favorite lyric in this sad ass song?

I think the title is my favorite lyric. I love a good parenthetical. This one is downright obsessive. It’s like (“in case you didn’t fully get what I mean when I say evening”).

This isn’t one of her most stunning songs in terms of lyrics or images. I do think it’s her saddest song. It’s about the inevitability of feeling left out. It’s about discerning and measuring loyalty and how it’s difficult to do this when the situational light is in transition–the murky space of the evening. I recognized (only last night) that this song is also hinting at a sense of community-based isolation. She says goodbye to her friends and “old sweethearts.”

It’s the most recognizable blues song of hers. The lyrics and semantic connections border on mundane, lulling you into a shared agitation and sadness. It reminds me of when I’m bored by my own inevitable feelings.

MC: Why is it that, in the nighttime, it’s so hard to tell who’s going to love you the best (and what exactly does ‘best mean’ (to you, at least))?

I think she’s making an observation about perception and distortion. For me the nighttime is when everything is intensified and hyper-saturated. I draw brighter connections and I become more obsessive. Who loves me and how is it measured? It’s hard to discern who your most loyal lovers are when it’s nighttime and they’re off doing god knows what. This song is about waiting for text messages. Tonight a bunch of my friends went to a party that I wasn’t invited to. I feel her.

MC: This is, like, not even close to being related to this sad ass song, but–the thing I love the most about your writing is that you’re so often either reinventing (or reclaiming) some awful parts of a person’s sexuality. How did that become something you were so interested in?

It’s so funny you ask this because I just wrote a poem where the speaker has a breastfeeding fetish. She wants to feed all her lovers and friends and participate in a larger culture of mothering. She snacks on baby food and fantasizes about pumping and leaking. I was thinking about jealousy and what I’m jealous of, and I realized I’ve always (since young girlhood) been jealous of mothers, not necessarily because they have babies, but because their bodies have another level that I have yet to unlock. The lactating breast as that secret room you find in your house in a dream.

My mom gave me a book about how it’s OK to masturbate when I was very young. I think that was my favorite book for many years. Since “healthy” (make those quotation marks heavier) (read: second-wave feminist) sexuality was a big part of my life and upbringing, I suppose I have an interest in subverting/questioning that specific language/ narrative around the happy and healthy and “normal” re: sexuality.

How to relate this to Dalton? Oh! This lyric from her feminist folk ballad “Katie Cruel” kinda sums up all my thoughts about the messiness, sheer exhaustion, and occasional delight associated with being/performing/moving as a woman with a body.

Through the woods I’m going
And through the boggy mire
Straight way down the road
‘Til I come to my heart’s desire

If I was where I would be
Then I’d be where I am not
Here I am where I must be
Where I would be, I can not

MC: When was the last time you cried? What were you crying about?

I’m not really into crying lately. I mostly well up. I’m trying to buck up. I don’t think that’s in fashion right now. I think the last time I cried was in November when I lost my phone for one hour.


Listen to the whole playlist right here:

Mark Cugini
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About The Author

Mark Cugini

Mark Cugini is managing editor of Big Lucks, a strategist for Real Pants, and the author of I'M JUST HAPPY TO BE HERE (Ink Press, 2014). Find him at

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