Vladimir Putin is the long-serving President of Russia, holding office since 1999. He was a KGB officer before his political career and has influenced Russia's political and economic landscape significantly.
This is based on winning 75 head-to-head matchups with other famous people, but also losing 36 head-to-head matchups.
Most recently Vladimir Putin lost a matchup to David Letterman (#1684) voted by someone from United States.