Headsigh
The headsigh is an ASCII portraying a man resting his head in his hands, seemingly agonized; based on an older "Aw Jeez, not this shit again!" image macro, featuring a real-life man making the same gesture.
Headsigh is usually posted together with the Captain Picard facepalm ASCII, the Ackbar ASCII, or just posted on its own to express frustration and disbelief. A common variation is to make a post with no image and "facepalm.jpg" as the text.
Headsigh was spammed endlessly from January 5-8, 2006.
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Facepalm
The original facepalm was of a man making the headsigh/facepalm gesture. Text associated with the macro was "Aww jeez, not this shit again". Later, Captain Picard was used to create the Headsigh ASCII and the associated macro that the ASCII was created from.
This facepalm image is used to denote disbelief at dumb comments or exasperating things done by another poster as if to say, "Oh God, not this again."
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Related articles
Gallery
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Classic example of the Headsigh ASCII being used
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The ultimate version of Facepalm