At some point in time, the pilot met Annie Stillwell, the wife of Billy Ray Stillwell. They had planned on killing Billy Ray, collecting the life insurance and getting married. One day, while Billy Ray was checking the crops, the Pilot flew over the crops and poisoned him with a strange toxic smoke. Billy Ray survived, but was horribly deformed.
When Billy Ray woke up after hours of unconsciousness, he went back to the farm and discovered Annie and the pilot kissing and overhearing their plans. In his anger, Billy Ray grabbed a garden hoe. The pilot escaped as Billy Ray proceeded to murder Annie. He then vowed to find the Pilot and kill him. One day, a mysterious man known only as Calypso visted Billy Ray in the Blackfield Asylum and offered him the chance to participate in the Twisted Metal contest. Billy Ray accepted.
In Billy Ray's ending, he is brought back to his farm by Calypso, where he discovers the pilot chained down with his plane running. Calypso told Billy Ray that in order to get his prize, all he had to do was "step aboard." As Billy Ray killed the pilot with his own plane, Billy Ray began to realize that he liked killing. He then decided to retire from farming and move into the city.
- In Billy Ray's ending, Calypso possessed the pilot's goggles and showed them to Billy Ray. However, when the pilot is shown, he is still wearing them. This could either be an error, or Calypso only possessed a duplicate pair of the pilot's goggles.