According to an article nearly 30 years ago in the county newspaper, the Advance Yeoman, the area acquired its unique name around the turn of the 20th century.

[3] A common joke in the region is to provide directions to the city of Paducah by saying "it's halfway between Monkey's Eyebrow and Possum Trot (a tiny community in Marshall County).

"[3] The community was formerly frequently mentioned in the sign-off message of WPSD-TV in nearby Paducah, as the location of its 1,638-foot-tall (499 m) broadcast transmitter.

[5] One theory on the origin of this unique name is that when looking at it from the air,[6] or on a map of Ballard County, it resembles a monkey's head.

[8] Yet another theory of the town's naming is that sometime before 1900, a community resident would go to nearby Needmore to get supplies, instead of going to the local general store and blacksmith shop built and owned by John and Dodge Ray, as the man didn't like his neighbors.