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2.
The hat worn by crazy French Revolutionaries, who were obsessed with the word "liberte'". The cap idea was stolen from the American Revolution, although they originate in Ancient Rome. They are often associated with the Freemasons, who played important roles in both revolutions.

Liberty Caps soon became synonymous with French patriotism and hatred of the aristocracy, just as Freedom Fries have become synonymous with Bushist "patriotism" and paranoia towards The French.

Ominously similar to those floppy hats worn by the Smurfs.
"A sea of red liberty caps swarmed about the guillotine." -Dickens "A Tale of Two Cities"
by El_Haggis September 08, 2006
 
1.
The type of magic mushroom found in Scotland (P. semilanceata)
yeah lets go pick some Liberty Caps
by Marshall Law November 12, 2004