Halftime Leisure

“Winner” by Conan Gray is a devastating deep dive into familial abandonment

September 22, 2023

Design by Rachel Zhang and Madeline Jones

In true Conan Gray fashion, the singer-songwriter’s new single “Winner” takes on the form of a vulnerable declaration—this time revealing the scars dealt by an absent, narcissistic parent. 

Best known for his downright depressing lyricism, “Winner” is not Gray’s first foray into songwriting that explores his complicated family history. Outside his typical motifs of broken romance, he has both hinted at and directly addressed his childhood wounds, from asking a friend to “Go wherever we want / ’Cause no one cares that we’re gone” in “Generation Why,” to questioning, “I watch the fathers with their little girls / And wonder what I did to deserve this” in “Family Line.” 

Gray’s never been afraid to expose the worst parts of his life, earning him titles like “Pop’s Oversharing Next Big Thing,” dubbed by Rolling Stone. It’s this openness that has earned Gray so many of his fans, whether it be those who identify with his lyricism or those who empathize with his trauma. In exposing his emotions to the world, Gray acts as a poster boy for those who want and need their feelings validated. This is best showcased in songs like the jealousy-laden “Heather” and the incredibly nostalgic “Grow”—and now, in the deeply melancholic “Winner.”

Gray has a knack for charming audiences with both his songwriting and his social media presence. More recent song promotion features snippets on official accounts prior to his singles’ releases, while concurrently showcasing a more personal narrative on his second, now private TikTok account, @user6141013131857. The 24-year-old has even gone so far as to make his own memes set to his singles. Still, the false bravado he displays on his official social media contrasts heavily against the more mellow, often self-deprecating humor posted on his throwaway account. 

When it comes to “Winner,” he’s been taking a few different approaches to promote it, posting himself screaming the lyrics while also using TikTok filters to give himself fairy wings. Though it seems almost absurd, it is a direct reflection of Gen Z’s ravenous consumption of his music and their typical quirky behavior. 

These silly little tactics by no means detract from the overwhelmingly raw tone of the song. He starts off “Winner” in the form of a simple ballad, nothing but a piano accompanying his voice. Gray sounds breathy and desperate as he recalls preparing to leave his home after being alone for days on end. He personifies “the pots and pans and roaches” claiming that “they’re glad I’m finally goin’ / ‘Cause, even them, they shudder at your name.” Here, he sows the seeds of a character so malicious as to forsake a 14-year-old, imagining even the pests recoiling at this abandonment.

The music slowly builds to a synthy and dramatic flourish—something he utilized fruitfully in his last release. Whereas “Never Ending Song” emulated the lightness of ’80s pop and had Gray experimenting with his lower register, giving him an almost standoffish, nonchalant vibe, “Winner” has him return to a higher vocal range, once again displaying his usual emotional depth.

Gray has mastered the use of his voice as his instrument, relying primarily on himself and his vocal prowess to convey what he is feeling. Here, he sounds like he is on the verge of tears at the song’s opening, something that noticeably shifts to anger partway through. Though he has used this technique before in other releases like “Jigsaw,” Gray adds additional dimension by introducing a wider range of instruments in the backing track to accompany his haunting vocals. Drumbeats at the initial chorus punctuate Gray’s animosity towards the persona he ironically refers to as the winner, because for him, “There’s no one / Who ever has done better / At makin’ me feel worse.” It is a cathartic moment, acting as the breaking point of a long-awaited realization.

“I wrote this song at 2 a.m.—everything at the piano just spilled out all at once,” Gray revealed in a statement to Rolling Stone. “It was a moment where I finally felt like, ‘Fine. Great job. You did it. You hurt me more than anybody ever could hurt me.’ And it oddly felt nice. I see now that there is a certain freedom that comes from recognizing that you’ve been hurt. In no longer running, and just facing the fact that ‘You win. You hurt me.’ I hope this song helps people find a little piece of that freedom.”

By the second verse, the song winds down but quickly builds back up as he ponders how he feels guilty when someone else is “the one who let it get this bad.” Gray oscillates between nearly yelling and defeatedly recounting his guardian’s wrongdoings, mimicking what a real fight between the two might look like. Still, even in this moment of weakness, he takes the high road rather than settling for low blows. In recognizing that “all you ever wanted was to fight / I was only tryin’ to survive your chaos,” Gray takes on a mature tone while simultaneously consoling his inner scorned child. 

In general, Gray’s discography isn’t crowd-pleasing in the way other pop is. It’s not safe, not fun, and not usually set to an upbeat tune. Even his hits tend to be bogged down by upsetting undertones, like doomed relationships and feelings of inadequacy. His music is, however, daring, as Gray bares his heart to the world, no matter the consequence.

Yes, it is corny to call “Winner” a winner; though in a way, it feels as though the song is repetitive, as the pre-chorus, chorus, and post-chorus play out, even opting out of a bridge. The lyrics also don’t seem particularly revolutionary, reiterating the same message over and over again—but in context it is this revelation that lends Gray the strength to attack his demons head on. The single truly succeeds in offering solace to all those who resonate with Gray’s message. Again, though it may be corny, that is enough to quite literally consider “Winner” a winner.

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