Gloria Estefan, a Cuban-American singer, has won eight Grammy Awards and is considered one of the greatest artists of all time by both VH1 and Billboard. She has sold over 100 million records worldwide.
This is based on winning 8 head-to-head matchups with other famous people, but also losing 18 head-to-head matchups.
Most recently Gloria Estefan lost a matchup to Jessica Biel (#459) voted by someone from United Kingdom.