Howard Stern
One of the biggest icons of the entertainment industry and someone who really revolutionized comedy. 
People with no brain will call him "a loser who is ugly and says stupid things..." etc.  but they miss the point that:
a)it is hard to call a man who is a radio legend and multi multi millionaire a "loser"
b)the man knows he is ugly and says stupid things, that is what his comedy is based on: stupid and controversial topics.

He is an unlikely celebrity and represents the underdog rather than being a complete fraud like many celebrities.  so if you don't like him then go fucking pop in a Julia Roberts movie while listening to a Madonna or Cher album becuase obviously you don't like honesty

DOUCHEBAGS
Howard Stern has ruled the radio airwaves for over 20 years

If you list the biggest comedy genius of all time you cannot leave Howard off that list