Wyclef Jean is a Haitian rapper, singer, and record producer known for his solo work and as a member of the Fugees. He has won three Grammy Awards and is noted for his philanthropic efforts.
This is based on winning 2 head-to-head matchups with other famous people, but also losing 22 head-to-head matchups.
Most recently Wyclef Jean lost a matchup to Hugh Hefner (#385) voted by someone from United Kingdom.