Stipulation matches in wrestling help break up the monotony of basic singles and tag matches and give manage an effective tool to use when promoting pay-per-views or major episodes of television. They drum up fan interest and present a new twist on an old concept. They are different and unique and for that reason, they will continue to remain incredibly popular. Over the course of wrestling history, however, some stipulation matches have proven to be incredibly inappropriate. Most have come from the mind of bookers and creative writers that rose to prominence during the Attitude Era but all have struck nerves for insulting one portion of the audience. Some have seen the personal freedom of human beings at stake while others saw the loser forced to kiss the winner's ass. Some were poorly conceived while others were insulting. Whether they featured beautiful blondes tearing at each other's clothing or two grown men shimmying up a giant pole to retrieve (insert object here), the matches have are notorious in the annals of professional wrestling history. Celebrate, denounce or approach indifferently history's 10 most inappropriate, and at times offensive, stipulation matches.