Country Star Trivia Comstock/Thinkstock How many CMA Entertainer of the Year trophies does Hank Williams, Jr. have? ANSWER: Two. Bocephus won in both 1987 and 1988. Copyright © 2015, ABC Radio. All rights reserved. Comments comments By ABC News|2015-11-04T10:00:56-06:00November 4th, 2015|Music News|Comments Off on Country Star Trivia Share This Story, Choose Your Platform! FacebookTwitterRedditLinkedInTumblrPinterestVkEmail About the Author: ABC News Related Posts