Achy Breaky Heart — Billy Ray Cyrus (1992)

Billy Ray Cyrus's mullet-forward cover for his 1992 hit 'Achy Breaky Heart' is the epitome of early-'90s country kitsch, with the hairstyle alone causing more cringes than any musical misstep. The album sold over nine million copies worldwide, yet its visual legacy is a cautionary tale in style over substance. The cover's generic backdrop and aggressive denim-and-bolo-tie aesthetic fail to elevate the music, making it a standout for all the wrong reasons in an era already marred by questionable fashion choices.