Country Star Trivia Comstock/ThinkstockHow many Entertainer of the Year trophies does Kenny Chesney have? ANSWER: Eight in all — 4 from the Country Music Association, and 4 from the Academy of Country Music. Copyright © 2016, ABC Radio. All rights reserved. Comments comments By ABC News|2016-04-04T10:01:00-05:00April 4th, 2016|Music News|Comments Off on Country Star Trivia Share This Story, Choose Your Platform! FacebookTwitterRedditLinkedInTumblrPinterestVkEmail About the Author: ABC News Related Posts