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Jason Sudeikis dancing in the background of "What's Up with That" kills me.

Going back a few years, the "Sully and Zazoo" skits with Jimmy Fallon and Rachael Dratch as idiotic Masshole teenagers is a favorite. Even Weebs...
 
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"Mastermind" with Phil Hartman as Ronald Reagan pretending to be a doddering fool for the public but actually being an energetic, domineering, abrasive, multilingual genius:

[ame=http://www.youtube.com/watch?v=skQuhoG7fFM]YouTube - The Real Ronald Reagan, as Portrayed by Phil Hartman[/ame]
 
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