Even before Sheppard became a series regular, Crowley felt like a central character to “Supernatural.” Most of the time, the powerful demon was giving the Winchesters trouble, but whichever side of the battle he was on, it was always exciting to have Crowley around. Sheppard stole the show with Crowley’s suave kind of sass that clashed with the brothers in just the right way. He even gave them the hilarious nicknames that became common usage among the show’s huge fanbase: Moose and Squirrel! But while he was definitely best known for speaking brutal insults and innuendos, the King of Hell also knew a thing or two about getting in touch with humanity from him. Those emotional moments became incredible high points of the series.
Sheppard recently looked back on his time on the series while speaking on a panel at Wizard World Chicago (via TellTaleTV), where he shared that one such moment stands above the rest:
“The season 8 finale is the most fun we’ve ever had. That was literally the best time for us. We shot the finale in sequence, and we were never more together than we were in that moment.”
The episode in question is “Sacrifice”, which marks the culmination of Sam enduring a series of trials to close the gates of Hell, with all demons sealed away forever. The final judgment requires him to heal a demon, and who better than his friend-enemy, Crowley? Although he is an unwitting participant, the ritual ends with some shocking revelations from the King of Hell as he slowly regains his humanity and confesses his desire to be loved. It’s not hard to see why this moment stands out for Sheppard, especially when he’s at the center of an already incredible episode.