10. Milton Berle, Actor (1908-2002)

  

Having lived until the ripe old age of 94, Berle clearly saw a lot of changes in his lifetime from 1908-2002. He had the distinction of being one of the America's first television stars on Texaco Star Theater in the 40's. How did he make such a name for himself? By dressing in drag, of course!
His cross-dressing shtick came from earlier vaudeville sensibilities, which were by no means edgy, but by introducing the concept to television, it reached many middle-American households that otherwise wouldn't know what fun it was to dress up in women's clothes!