The night was filled with countless collaborations ranging from Garth Brooks and Trisha Yearwood to the Dixie Chicks and Beyoncé. Brad Paisley capped off the show with a moving performance of his new single "Today," recognizing that the 50th Annual CMA Awards would be a day to remember for a lifetime, especially for the artists who took home an award.
Dolly Parton received the Willie Nelson Lifetime Achievement Award, and was honored with a star-studded tribute that started with Pentatonix and Jennifer Nettles singing "Jolene," followed by Reba breaking out into "9 to 5," and was wrapped up with a beautiful rendition of "I Will Always Love You" from Kacey Musgraves, Martina McBride, Jennifer Nettles, Reba, and Carrie Underwood.
Four-time Entertainer of the Year winner Kenny Chesney was presented with the Pinnacle Award by Peyton Manning, which represents an artist that has acheived global prominence for country music. Only two others have received this award before Chesney: Garth Brooks and Taylor Swift.
Taylor Swift returned to the stage to present the night's biggest award, Entertainer of the Year to Garth Brooks. His last win in the category was in 1998 and this was his fifth EOTY win.
Female Vocalist of the Year went to Carrie Underwood, her first win in the category since 2008. Reigning CMA Male Vocalist of the Year Chris Stapleton was once again a winner in the category.
Vocal Group of the Year was awarded to Little Big Town, who also shared a performance of their new single "Better Man," which was written by Taylor Swift. Brothers Osborne received their first win for Vocal Duo of the Year. The duo was visibly shocked by the award, saying they didn't even prepare a speech.
New Artist of the Year Maren Morris had tears rolling down her face as she accepted her award, and exclaimed that she had great seats this year. "I sat at a bar across the street and watched the show last year." She was joined by the Preservation Hall Jazz Band for a performance of "My Church" that brought everyone in the arena to their feet.
Single of the Year went to "Die A Happy Man" by Thomas Rhett, which he also performed later in the show. His wife Lauren was beaming as her husband received his first CMA award. The Song of the Year award was given to "Humble and Kind," written by Lori McKenna. The song is a prayer that she wrote for her five children, who were all in attendance at the show. Later in the show, Tim McGraw gave a moving performance that included a choir of children joining him on stage.
Album of the Year was awarded to Eric Church for Mr. Misunderstood, which was released as a surprise this time last year. Faith Hill presented Church with his trophy, and he said, "I'm not sure what is better, winning this award or Faith Hill fixing my tie!"