Conan Gray’s new single Checkmate fuses old and new

Conan Gray's new single feels like a throwback to 2000s pop rock while still feeling fresh.


As Conan Gray’s ‘Checkmate’ opens, the new single throws listeners back to the late 2000s. It builds with one of those classic introductory crescendos we heard on tracks by The Maine and The Click Five that ruled radio back when we were still messaging on AIM and actually watching MTV’s top music video countdown on television

But after only five seconds, the song pivots. For the rest of the first verse, it’s a synth-pop, beat-heavy slow jam firmly rooted in 2019, demonstrating how much music has shifted and tastes have changed. 

Then on the chorus, it’s back to the upbeat pop sound we were entrenched in ten years ago, but with new influences that connect the beat back to the current day.

The juxtaposition inherent to ‘Checkmate’ defines the song. There are references to well-known classics (“Build Me Up Buttercup” “Cry Me a River”) in the lyrics, but it still feels like a modern heartbreak anthem. Gray croons “‘Cause I’ve gotten tired of the games that you play / When you tell me you love me then you throw me away” and the Gen Z’s currently experiencing their first crush on someone who doesn’t reciprocate their feelings can relate—but so can millennials who grew up listening to “Just the Girl.” It’s simultaneously a timeless complaint and a product of the moment. 

At its core, ‘Checkmate’ is a delightful bubblegum pop tune whose beat grows on the listener with each play. The journey through different yet cohesive sounds is perfectly suited to being played on repeat, preferably while dancing with abandon in your bedroom. By the second listen, you’ll be able to sing along to the predictable lyrics, but this makes it no less fun or relatable. In fact, it just makes ‘Checkmate’ more delightful.  

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