Will Dierks Bentley finally win his 1st Grammy with help from Elle King?

Country singer Dierks Bentley is moving up on a list he probably doesn’t want to be on anymore. He has been nominated for 12 Grammys and has lost each one. Currently he’s tied as the ninth most nominated artist without a win, and he’s in second place among country artists, behind Martina McBride with 14 unsuccessful Grammy bids. Can Bentley finally win this year with a little help from Elle King?

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Bentley and King are nominated for Best Country Duo/Group Performance for their collaboration “Different for Girls” from his latest album, “Black.” This is his 13th nomination and her third, and though this is the only nomination for either of them this year — “Black” was snubbed for Best Country Album — the song is already a proven winner, having claimed Vocal Event of the Year at the 2016 CMA Awards. So can he finally put one in the win column?

Another pop star is nominated in this race for joining forces with an overdue country favorite: Pink, who is nominated for “Setting the World on Fire” with Kenny Chesney. Pink has won three Grammys, but now she’s hoping to push Chesney to a long-awaited first win. Like Bentley, Chesney has never won, but though Chesney has earned fewer nominations he has been waiting much longer: his career goes back more than 20 years, including multiple Entertainer of the Year victories at both the ACM and CMA Awards, but Grammy continues to elude him.

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They’ll both have to get past the legendary Dolly Parton, nominated for a version of her iconic song “Jolene” performed with a cappella group Pentatonix. Parton has won seven Grammys out of a whopping 47 career nominations; she’s even been nominated twice before for “Jolene”: Best Country Female Vocal in 1975 for a recorded version and in 1976 for a live version. But she has never won for the song even though it’s one of her most famous, and she hasn’t won in any category since 2002. However, Pentatonix won their first Grammy just two years ago, so perhaps their unconventional team-up will be the key to victory for both.

Chris Young is nominated for “Think of You,” his duet with Cassadee Pope, who won season three of “The Voice” in 2012. As we’ve seen from Carrie Underwood‘s impressive track record Grammy voters are more than willing to embrace reality TV champs. But this would be the first Grammy victory for both of them.

Rounding out the category is “21 Summer” by the Brothers Osborne, who are the only established country group in a category full of collaborations, so perhaps that will help them stand out. They’re relative newcomers, having released their debut album “Pawn Shop” in January 2016, but this is their second straight nomination in this category.

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