The 1999 Country Music Association Awards, the 33rd edition of the Country Music Association Awards, was held on September 22, 1999, at the Grand Ole Opry House in Nashville, Tennessee. It was hosted by Vince Gill.
Tim McGraw and Vince Gill had the most nominations, five each.
The awards show, broadcast on CBS, was notable for an incident involving the song "Choices" by George Jones. The Country Music Association (CMA) had invited Jones to perform it during the show, but required that he perform an abridged version. Jones refused, and did not attend the show. Alan Jackson was angry with the CMA's decision, and mid-performance of his song "Pop a Top" during the show, played the chorus of Jones' song in protest, before angrily exiting the stage to a long standing ovation.
Winner are in bold.