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| The man that holds the Guinness Book of World Records' title of the world's largest penis explains the challenges of living so well endowed. TLC , views. Behind Bars: The World’s Toughest Prisons - Dallas County Jail, Texas, USA (Eps. EWAN McGregor has one of the "biggest willies in Hollywood", Sun Online can reveal. The Scots actor, 47, has been included a list of the "10 Biggest Penises in Hollywood", compiled by Mr Man, a database for male celebrity nude scene. Gone Girl actor Ben Affleck, 46, who has done.