The Masochistic Tendency of Pop in Conan Gray’s ‘Heather’

The Masochistic Tendency of Pop in Conan Gray’s ‘Heather’

Conan Gray pens a painfully honest account of longing—one that fits right into pop music’s library of tracks about unrequited love



When Conan Gray released the tracklist of his debut album Kid Krow on Twitter, he made it clear that the sadness in Heather would be unbearable. “Sadness is subjective,” he tweeted, “but Heather makes me want to decompose and melt through the floorboards.”


In February, he would again tell Twitter about the forlorn this song bears. “[Heather] makes me want to die, and I’m tired of being the only one crying. I want y’all to cry with me.” And as if it requires more weight, he added: “Heather is the kind of song that deserves ‘heather – conan gray (crying alone in the rain)’ edits.”



Conan was talking about a type of DIY remix in which a song is slowed down and edited to sound like it’s being played elsewhere. Usually accompanied by a looping animated image culled from an ’80s or ’90s Japanese anime, this type of music edit has become so prevalent on YouTube. If you let the algorithm take its course, you would end up listening to one of those edits one way or another.


Channels that make this kind of edit heeded Conan’s suggestion. By April, a YouTube channel uploaded an edit titled “heather by conan gray but it’s even sadder.” The accompanying visual is of a section in the theater close to the exit door. Amid the perpetual flicker of the theater projector, a man sits still with his chin perched on one hand. As Conan had imagined, the song plays with the sound of gentle rain in the background. And it is satisfyingly sad.



Heather is a song about unrequited love. Here, Conan writes about a person whom he was in love with for all four years of high school. This person cared about Conan and even loved him, too. Their affection was enough for them to lend Conan their sweater, but not large enough to give it to him. The sweater, so does their love, goes to a girl named Heather.


“She was perfect and beautiful and so sweet. Because of that, I was so jealous of her and I hated her so much,” says Conan. “And she did not deserve [all that hate] at all.”


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Heather belongs to a territory of pop music where the singer seems to ravish in pain. And Heather, the character, is so commonplace in this realm. And it is important to note that her existence is peripheral and is often mentioned in passing.


Her existence is the last thing the singer wants to bring up, but the conversation inevitably leads to her. And that’s not because the boy adores her so much. Instead, it is the singer who desperately steers the conversation to her. Think sentences that only take slip into conversations after the conjunction “soooooo.” It’s an act of self-deprecation that subjects the singer further into the pain. One can find this in Carly Rae Jepsen’s Your Type. “I bet she acts so perfectly /You probably eat up every word she says,” muses Jepsen in the second verse of this anthemic hit from Emotion. Then, she proceeds to tell both her and the boy how little she is: “I bet I’m just a flicker in your head.”


Taylor Swift, whom Conan calls his mother (“I feel like I was raised by Taylor Swift,” he chirps in an interview with Seventeen), has placed the character in a handful of her songs, too.


You Belong with Me, for example, describes a stereotypical high school queen bee (“she wears short skirts,” “she wears high heels,” “she’s cheer captain”). In Invisible, Taylor doesn’t describe the girl, but she tells the listener how the boy “stops and stares whenever she walks by.” Both songs find triumph, though. Taylor presents the other girl as someone who doesn’t return the same looks and the same care. But if there is an embodiment of Heather in her songs, it’s the girl Drew likes on Teardrops on My Guitar.


Teardrops on My Guitar is the first video Conan watched on YouTube and perhaps his gateway to his mother’s music. Here, Taylor sings about a boy named Drew whom she secretly liked in freshman year. Oblivious as he was, the boy—who in real life tried to reconnect with Taylor after the song became a hit—kept telling Taylor about all the girls he fell head over heels for. “I bet she’s beautiful / that girl she talks about / And she’s got everything that I’ve had to live without,” sings Taylor.


But unlike the diffident jealousy on Your Type and Teardrops on My Guitar, Heather conveys a straightforward profession of envy that mutates into earnest admiration and slips back to hate.


“You gave her your sweater / It's just polyester, but you like her better / Wish I were Heather,” sings Conan in the chorus. Then in one verse, he goes, “But how could I hate her? / She's such an angel / But then again, kinda wish she were dead.”


Heather is not all bitter. Underneath the melancholia, Conan seems to express a certain degree of happiness for the person he loves. It hurts, but at least they have found somebody to love. However, none of this affection is expressed towards himself.


But if Heather and the other songs mentioned could admit pain, why does the singer remain complacent?


Heather’s forebears narrate a vicious cycle of desire and pain with no redemption. Still, even if the white flag has been raised, there is willingness to experience the same suffering again and again.


“And I break all the rules for you / Break my heart and start again / I'm not the type of girl you call more than a friend,” sings Carly. Meanwhile, on Teardrops on My Guitar, Taylor resolves to continue hiding her feelings instead of forgetting about Drew: “Drew looks at me / I fake a smile so he won’t see.”


Heather doesn’t do that implicitly. The song ends with a chorus that doesn’t mention Heather. “I wish I were,” the song concludes. It implies a vague resolution. The melancholia in his voice suggests surrender, but only because of exhaustion. Maybe the thought of Heather still lingers in Conan’s head.


It is on another song from Kid Krow that Conan presents himself as a willing victim.


Sonically more angsty than Heather, The Cut That Always Bleeds tells the story of a person who only returns to Conan after their lover leaves them.


The character Conan builds in The Cut That Always Bleeds is sensible. “Oh, I can't be your lover on a leash / Every other week, when you please,” he protests in the chorus. But towards the end, he falls weak. “But even though you're killing me / I, I need you like the air I breathe / I need, I need you more than me,” the bridge goes. The final chorus then forgoes what is established earlier: That the singer deserves to be treated better. “'Cause I could be your lover on a leash / Every other week, when you please / Oh, I could be anything you need /As long as you don't leave.”


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In an interview at the Zach Sang Show, Conan says that he tends to place his affection on people whom he knows would never be able to love him back. It is not because he doesn’t want to feel loved. Instead, he considers it a way of protecting himself, even if the very act only leads to suffering. “Every once in a while, you just kind of want to be obliterated. Because being obliterated is better than feeling nothing,” he says.


Perhaps that explains the prevalence of masochistic tendencies in this particular type of sad pop songs. The expression of desire to suffer is just a desperate attempt to hold on to a feeling. It may not be the ecstasy or the bliss of pure love, but at least it’s a feeling. To wallow in an agony that resulted from an experience of love is still better than simply experiencing the plain dread of existence.


It is foolish to subject oneself to suffering just to feel. But what is there to do? Not everyone can pull an Adele and say, “never mind I’ll find someone like you.” Even that is a result of an agonizing recollection. And perhaps that is the very reason why this kind of sad pop song about one-sided longing keeps re-emerging: Remembering the pain is the very bridge that gets the singer, as well as the listener, to the side of healing. It’s catharsis.


It’s this process that enabled Conan to reassure us during a recent chat that he no longer wishes to be the lovely Heather.


“I just have come to accept who I am. I’ll never be Heather. I’ll never be that lovable sweet perfect person ever. I’ll never be, no matter how hard I try,” he says. “[What I need is] somebody who loves me for me, not somebody who loves me for how much I want to be Heather. And I think we should all look for that.”



Words Oliver Emocling
Special thanks to MCA Music, Inc.

Art Matthew Ian Fetalver

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