According to the combined predictions of hundreds of Gold Derby users, Chris Stapleton is the front-runner to win both Single of the Year and Song of the Year for “You Should Probably Leave.” If we’re right it would be his second win in a row for Single of the year and his third overall in the category. That would actually set a new record since to date no one has ever won Single of the Year more than twice.
Stapleton previously claimed Single of the Year for “Broken Halos” (2018) and “Starting Over” (2021). As it stands that ties him with seven other artists who have prevailed twice: Alan Jackson (“Chattahoochee” and “Where Were You When the World Stopped Turning”), George Strait (“Check Yes or No” and “I Saw God Today”), Johnny Cash (“A Boy Named Sue” and “Hurt”), Lady A (“I Run to You” and “Need You Now”), Lee Ann Womack (“I Hope You Dance” and “I May Hate Myself in the Morning”), Little Big Town (“Pontoon” and “Girl Crush”), and Willie Nelson (“Good Hearted Woman” and “Always on My Mind”). Of those, only Lady A won consecutively, as Stapleton is looking to do.
This isn’t a done deal for Stapleton, though. Far from it. While he’s backed by 14 of the Top 24 Users who got the highest scores predicting last year’s CMAs, there are five who say it will be Carly Pearce and Ashley McBryde‘s “Never Wanted to Be That Girl.” Three are betting on Cody Johnson‘s “Til You Can’t.” And two are betting on Kelsea Ballerini‘s “Half of My Hometown” featuring Kenny Chesney. None of them have won this award before, and under normal circumstances you’d think that would be a disadvantage for them against a two-time champ, but clearly the Country Music Association likes to spread the wealth, so you should probably hedge your bets .
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