5. "Harry Caray: Space, the Infinite Frontier"
Show: Saturday Night Live
Year aired: 1997
Star: Will Ferrell
Will Ferrell's best known for his George W. Bush impression, but his take on Harry Caray is by far his most convincing. In this skit, Ferrell does the legendary Cubs announcer as the host of a show about space. The most hilarious moment comes when Caray prefaces a question with "We all know that the moon is not made of green cheese," and continues, "but what if it were made of barbeque spare ribs, would you eat it then?"