The Outlaw Josey Wales
The town was the site of the September 1861 Sacking of Osceola by Jayhawkers (anti-slavery patrols) in which the town was burned and its courthouse looted. The event inspired the 1976 Clint Eastwood film "The Outlaw Josey Wales". Prior to the attack the town had a population of around 2,500. However, fewer than 200 residents remained after the event and the population has never again approached those numbers.