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20 Songs Behind Chris Stapleton's Award Show Dominance

Chris Stapelton's newest material should further his haul of award nominations.

Few current stars equally appease mainstream country fans, traditionalists and even casual pop listeners quite as effectively as Chris Stapleton.

Ultimately, that's because his musical output casts a wide creative net. Dave Cobb co-productions Traveller, From A Room: Volume 1 and From A Room: Volume 2 — two of which are CMA Album of The Year winners — have pockets of music that were meant for wide listenership. As does his most recent LP, 2020's Starting Over. Indeed, while Stapleton is certainly a true-blue country singer, he's so much more than that. His classic country callbacks, southern rock ramblers and intimate storytelling narratives all resonate. His soulful vocal runs and bluesy guitar grit are refreshing and worthy of critical acclaim.

His musical range can be chalked up to his time with the Kentucky bluegrass group The SteelDrivers and the Southern rock outfit The Jompson Brothers. His career as a Nashville songwriter (we're talking over 100+ songs) is the stuff of legend. But there's a reason those songs were recorded by the likes of Kenny Chesney, Thomas Rhett, Luke Bryan, George Strait, Brad Paisley, Lee Ann Womack, Dierks Bentley, Darius Rucker and even Adele. It's because they tapped into something that spoke to their vast audiences. When it came time for Stapleton to fly solo, that tap wasn't turned off. Instead, he let the levee break.

While the catalog of Stapleton songs is diverse in style and story, like the rollicking "Midnight Train to Memphis" or the rhythmic "Trying to Untangle I Mind," it's his genuineness that remains reliable throughout. It'd be easy to dole out a series of paint-by-numbers songs that would find their way to the top of the charts. But Stapleton has rarely, if ever, released a song for the simple fact that he's a fixture of industry awards shows.

Stapleton certainly checks off most boxes as an artist— amazing and powerful vocals, pure raw emotion, heartfelt lyrics and an earnest ear for melody. Yet perhaps his single greatest gift is his ability to time and again deliver songs that feel comfortable and familiar. Singles and album tracks become anthems and in turn, those anthems insist on being sung along with. Chorus lines are easily learned. They're identifiable and universal.

Still, Stapleton doesn't rely too much on that. His most intimate songs are cherished not only because he takes you on "hurt so good" journeys, but because even his grizzled vocals resonate. He channels the raw emotions of a moment with his delivery in ways most singers only dream about.

All being said, Stapleton's country albums are rich journeys that shed light on some of your deepest thoughts and darkest trials while celebrating your highs of satisfaction and joy. Here's our playlist of the 20 best Stapleton songs.

Editor's Note: This story previously ran on Nov. 9, 2022.

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