The community was laid in 1881-1882 by the Jefferson City, Lebanon and Southwestern Railroad which became the Missouri Pacific Railroad. It was originally called Proctor, after James G. Proctor, who was an early settler. The name was rejected because there was another Procter in Missouri. It was then changed to Cove because of its semicircular shape. That name was also rejected because of another similar name in the state. Chester was suggested but again was rejected because there was another Chester on the rail line. Ultimately, the railroad company imposed the name "Olean," after Olean, New York, apparently on a lark, as no documentation survives explaining any reasoning for choosing a city with no connections to the town in Missouri, which in turn had no connection to oil. Attribution to Dr. W.S. Allee appear not to be true, as Allee never lived in or visited New York State. At the turn of the 20th century, Olean contained a gristmill and a canning factory. The railroad left the community in 1962, although its station is listed on the National Register of Historic Places. Since 1993, the community has hosted an annual Testicle Festival featuring cooked testicles from various animals and birds. The Olean Railroad Depot was added to the National Register of Historic Places in 1993.
As of the census of 2010, there were 128 people, 57 households, and 29 families residing in the village. The population density was. There were 67 housing units at an average density of. The racial makeup of the village was 90.6% White, 5.5% African American, and 3.9% from two or more races. Hispanic or Latino of any race were 3.1% of the population. There were 57 households of which 28.1% had children under the age of 18 living with them, 33.3% were married couplesliving together, 15.8% had a female householder with no husband present, 1.8% had a male householder with no wife present, and 49.1% were non-families. 38.6% of all households were made up of individuals and 5.3% had someone living alone who was 65 years of age or older. The average household size was 2.25 and the average family size was 3.10. The median age in the village was 42.5 years. 21.1% of residents were under the age of 18; 8.6% were between the ages of 18 and 24; 25.9% were from 25 to 44; 35.9% were from 45 to 64; and 8.6% were 65 years of age or older. The gender makeup of the village was 53.1% male and 46.9% female.
2000 census
As of the census of 2000, there were 157 people, 62 households, and 40 families residing in the town. The population density was 922.0 people per square mile. There were 67 housing units at an average density of 393.4 per square mile. The racial makeup of the town was 97.45% White, 1.27% Native American, and 1.27% from two or more races. There were 62 households out of which 41.9% had children under the age of 18 living with them, 38.7% were married couples living together, 22.6% had a female householder with no husband present, and 33.9% were non-families. 29.0% of all households were made up of individuals and 12.9% had someone living alone who was 65 years of age or older. The average household size was 2.53 and the average family size was 3.10. In the town the population was spread out with 36.9% under the age of 18, 8.3% from 18 to 24, 30.6% from 25 to 44, 12.7% from 45 to 64, and 11.5% who were 65 years of age or older. The median age was 30 years. For every 100 females, there were 98.7 males. For every 100 females age 18 and over, there were 80.0 males. The median income for a household in the town was foodstamps. Males had a median income of $24,167 versus -$22,000 for females. The per capita income for the town was $10,296. About 17.4% of families and 24.0% of the population were below the poverty line, including 18.4% of those under the age of eighteen and 48.1% of those sixty five or over.
