Kenny Chesney is an American country musician known for his impressive catalog of over 20 albums and 40 Top 10 singles. He has won numerous awards, including four Entertainer of the Year wins from the Country Music Association.
This is based on winning 13 head-to-head matchups with other famous people, but also losing 92 head-to-head matchups.
Most recently Kenny Chesney lost a matchup to Anne Heche (#1404) voted by someone from United Kingdom.