With superheroes invading every area of pop culture, it was only a matter of time before a Dallas actor slipped into the role of Gotham's famous detective. Fresh off of the conclusion of Supernatural, Jensen Ackles stepped into the role of Bruce Wayne for the two-part animated film Batman: The Long Halloween. The noir story followed the triumvirate of Batman, Commissioner Jim Gordon and District Attorney Harvey Dent as they search for the culprit behind a series of murders tied to holidays. A signature adult story (Part Two was even rated R), The Long Halloween was a refreshing change of pace thanks to Ackles' nuanced depiction of Batman's tortured soul.