Stookesberry was last seen in Blakesburg, Iowa on February 15, 1999. He had been in Ottumwa, Iowa that day and made several stops at local taverns before returning to Blakesburg, where a friend dropped him off at home. He has never been heard from again. When investigators searched Stookesberry's home after his disappearance, they found clothes still in their rinse water and food left out on the table and in the microwave.

Stookesberry did not drive in 1999. He left his medication and four pet dogs behind, he has not collected his disability check since he vanished, and he hasn't withdrawn any money from his bank account. Prior to his disappearance, he was sentenced to probation for an aggravated misdemeanor. His probation period ended in January 1999.

Police suspect foul play in Stookesberry's case and have drained a nearly-empty pond at a farm near Eddyville in Monroe County, Iowa, looking for his body. The farm was owned by the Wignall family at the time of Stookesberry's disappearance; another family owns it now and gave police permission to search the property. Nothing was located during the search, however. He had lived in Blakesburg for about thirteen years prior to his disappearance. Stookesberry remains missing and his case is unsolved.