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Charley Pride and His Rendition of Hank Williams’ Widely-Covered Song “You Win Again”

Charley Pride and His Rendition of Hank Williams’ Widely-Covered Song “You Win Again”
by
  • Riley is a Senior Country Music Journalist for Country Thang Daily, known for her engaging storytelling and insightful coverage of the genre.
  • Before joining Country Thang Daily, Riley developed her expertise at Billboard and People magazine, focusing on feature stories and music reviews.
  • Riley has a Bachelor of Arts in Journalism from Belmont University, with a minor in Cultural Studies.

Country singer Charley Pride joined the long list of artists who covered Hank Williams’ 1952 B-side track “You Win Again.” His 1980 version was a number-one hit, earning him his 28th career chart-topper. And deservingly so. Pride was able to inject his unique artistry into the song and reflect the changing cultural landscape of country music at the time without taking away the essence of Williams and his message in the song. 

“You Win Again” is a painfully distraught ballad recorded a day after Williams’ divorce from his ex-wife Audrey was finalized. That raw heartbreak definitely tore into the song, marking it with a palpable emotional intensity and vulnerability that conveyed an immediate feeling of sorrow and betrayal. Williams’ nasally, high-pitched delivery highlighted this even more. On the other hand, Pride’s rendition was more controlled and polished sounding, with his smooth baritone providing that sense of calm resignation. It was still heartbreak, but a different kind. 

As every country music fan would know, Pride was no stranger to heartbreakers. One of Charley Pride’s classics was “Does My Ring Hurt Your Finger.”

Aside from the approach, the track arrangement also had subtle differences. The original was more stripped-down, typical of the ‘50s honky-tonk style, with features of guitar, fiddle, and pedal steel guitar. It’s less produced and more straightforward. Pride featured a fuller production with a rich array of instruments and gave it a lush and layered feel. 

Despite the changes, the lamenting nature of the song and its melancholic message remained intact. 

“You Win Again” was one of the 12 songs Charley Pride covered from the country legend’s discography for his album There’s a Little Bit of Hank in Me. And he definitely proved that. The album peaked at number 1 on the Billboard Top Country Albums. 

Listen to Charley Pride’s cover of Hank Williams’ “You Win Again” in the video below. 

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