2000
The Chicks, “Cowboy Take Me Away”
Toby Keith, “How Do You Like Me Now?!”
Kenny Rogers featuring Alison Krauss and Billy Dean, “Buy Me a Rose”
Faith Hill, “The Way You Love Me”
Lee Ann Womack featuring Sons of the Desert, “I Hope You Dance”
Alan Jackson, “It Must Be Love”
Jo Dee Messina, “That’s the Way”
John Michael Montgomery, “The Little Girl”
Travis Tritt, “Best of Intentions”
Phil Vassar, “Just Another Day in Paradise”
Tim McGraw, “My Next Thirty Years”
2001
Toby Keith, “You Shouldn’t Kiss Me Like This”
Keith Urban, “But For the Grace of God”
Jamie O’Neal, “There is No Arizona”
Brooks & Dunn, “Ain’t Nothing ‘Bout You”
Kenny Chesney, “Don’t Happen Twice”
Tim McGraw, “Grown Men Don’t Cry”
Jamie O’Neal, “When I Think About Angels”
Toby Keith, “I’m Just Talkin’ About Tonight”
Cyndi Thomson, “What I Really Meant to Say”
Alan Jackson, “Where I Come From”
Brooks & Dunn, “Only in America”
Tim McGraw, “Angry All the Time”
Toby Keith, “I Wanna Talk About Me”
Alan Jackson, “Where Were You (When the World Stopped Turning)”
2002
Steve Holy, “Good Morning Beautiful”
Tim McGraw, “The Cowboy in Me”
Jo Dee Messina featuring Tim McGraw, “Bring On the Rain”