1999 Country Music Association Awards


The 1999 Country Music Association Awards, 33rd Ceremony, was held on September 22, 1999 at the Grand Ole Opry House, Nashville, Tennessee, and was hosted by CMA Award Winner, Vince Gill.
Faith Hill lead the night with 7 nominations, including Album of the Year, and Entertainer of the Year

Winners and Nominees

Winner are in Bold.
Entertainer of the YearAlbum of the Year

  • A Place In The Sun - Tim McGraw
  • * Always Never The Same - George Strait
  • * The Key - Vince Gill
  • * Two Teardrops - Steve Wariner
  • * Where Your Roads Lead - Trisha Yearwood
  • Male Vocalist of the YearFemale Vocalist of the Year
  • Tim McGraw
  • * Vince Gill
  • * Alan Jackson
  • * George Strait
  • * Steve Wariner
  • Martina McBride
  • * Faith Hill
  • * Jo Dee Messina
  • * Shania Twain
  • * Trisha Yearwood
  • Vocal Group of the YearVocal Duo of the Year
  • Dixie Chicks
  • * Alabama
  • * Diamond Rio
  • * Lonestar
  • * The Wilkinsons
  • Brooks & Dunn
  • * The Kinleys
  • * The Lynns
  • * Montgomery Gentry
  • * The Warren Brothers
  • Single of the YearSong of the Year
  • "Wide Open Spaces" - Dixie Chicks
  • * "Amazed" - Lonestar
  • * "Choices" - George Jones
  • * "Don't Laugh At Me" - Mark Wills
  • * "Please Remember Me" - Tim McGraw
  • "This Kiss" - Robin Lerner, Annie Roboff, and Beth Nielsen Chapman
  • * "Don't Laugh At Me" - Allen Shamblin and Steve Seskin
  • * "Husbands And Wives" - Roger Miller
  • * "If You Ever Have Forever In Mind" - Vince Gill and Troy Seals
  • * "Please Remember Me" - Rodney Crowell and Will Jennings
  • Horizon AwardMusician of the Year
  • Jo Dee Messina
  • * Kenny Chesney
  • * Sara Evans
  • * The Wilkinsons
  • * Chely Wright


  • Music Video of the YearMusic Event of the Year
  • "Wide Open Spaces" - Dixie Chicks
  • * "Don't Laugh At Me" - Mark Wills
  • * "How Forever Feels" - Kenny Chesney
  • * "I'll Go On Loving You" - Alan Jackson
  • * "Just To Hear You Say That You Love Me" - Tim McGraw and Faith Hill
  • My Kind Of Woman/My Kind Of Man - Vince Gill and Patty Loveless
  • *No Place That Far - Sara Evans and Vince Gill
  • * Old Dogs - Waylon Jennings, Mel Tillis, Bobby Bare and Jerry Reed
  • * Same Old Train - Clint Black, Joe Diffie, Merle Haggard, Emmylou Harris, Alison Krauss, Patty Loveless, Earl Scruggs, Ricky Skaggs, Marty Stuart, Pam Tillis, Randy Travis, Travis Tritt and Dwight Yoakam
  • * TRIO II - Dolly Parton, Emmylou Harris, and Linda Ronstadt
  • Hall Of Fame