Manny Pacquiao is a Filipino politician and former professional boxer, widely regarded as one of the greatest boxers of all time. He is the only eight-division world champion in boxing history and has served as a senator in the Philippines.
This is based on winning 5 head-to-head matchups with other famous people, but also losing 14 head-to-head matchups.
Most recently Manny Pacquiao lost a matchup to Jada Pinkett Smith (#478) voted by someone from Canada.