Dylan was part of the militia that saved Sam and Dean from demons near Blue Earth, MN. He later participated in an attack on a demon nest near the town, during which he saved Dean's hide twice. Grateful for his help, Dean agreed to let him ride back to town with him and Sam in the Impala. Unfortunately, as they were sharing a beer, a lone demon hiding underneath the car grabbed Dylan's ankles and dragged him under. Sam managed to kill the demon, but not before it slashed Dylan's throat.
The Whore of Babylon later uses his death to trick his parents into committing sin.