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Chasing the donkey

Chasing the donkey is a slangism used to describe a continuation of an activity despite drastically diminishing returns. Originally specifically applied to the continued smoking of cannabis despite the user not being able to achieve a greater sense of euphoria, the drive to attempt a more impaired state is described anecdotally as "chasing the donkey." The term has since been applied to other activities such as drinking with the common relationship being that the activity is detrimental to one's moral, physical, or professional well-being. The person or persons participating in this activity have full or partial awareness that the continuation of this activity is unnecessary and/or harmful, yet they persist in committing this activity for no apparent reason.
History
This phrase was heavily used in the 1930s just prior to the enactment of the Marijuana Tax Act of 1937. It seems to have gained prominence during prohibition and was first thought to be a phrase of African American jazz artists who migrated from rural communities during the urbanization of the early twentieth century.
While the exact origin of this phrase is unclear, its use in the 1930s and revival in the late 1960s have given it an underground pop culture status that persists in the vernacular of the American cannabis community to the present time.
More recently, it has been applied to the 2008 American presidential race where the stubbornly repeated fruitless attempts of the republican candidate (a political party represented by an elephant mascot) to surpass the polling data of his democratic rival (a political party represented by a donkey) resulted in the use of this term as a double entendre. Whether this use was intentional by all persons and organizations is not known, however, its recognition by a subset of the American population has once again thrust this phrase back into the language of modern American popular culture.
While the exact reason for a donkey being used as the target of this idiom is unknown, at least two prominent theories have come into favor.
First, it is thought that because the Donkey is a stereotypically stubborn animal, chasing one and catching it when it does not want to be caught is a very difficult task. Thus "chasing the donkey" is a pointless endeavor that will not be beneficial. This reasoning is applied to the game Pin the Tail on the Donkey and has some basis in the Christian Bible (1st Samuel 9:1-5 ) where Saul spends several days in a fruitless effort to find some lost donkeys.
The second theory applies more directly to the person the phase is applied to. The donkey is also known as an ass due to it's species name "Equus asinus" and in American English an ass is a derogatory term when used to describe another. Thus by "chasing the donkey" the person described is willfully continuing an activity that is considered by others to be foolish or stupid.



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