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With this win, Chris Stapleton became the first artist ever to be awarded Male Vocalist of the Year six times.
The 56th Annual 'Biggest Night of The Year' took place on November 10th at the Bridgestone Arena in Nashville, Tennessee.
Combs is the first person to win Entertainer of the Year for two years in a row since Garth Brooks won in the category in 2016 and 2017.
The single is taken from Combs' album, Growin' Up, which went on to win the CMA 2022 Album of the Year.
Celebrating their shared home state of Kentucky, the live collaboration follows their appearance at October's Kentucky Rising concert.
The festival, which is taking place on April 28-30 2023, will feature Spoon, The Head and the Heart and Jason Isbell and the 400 Unit.