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Sheppard was pleasantly surprised when he learned that he'd get to explore Crowley's mommy issues this season.

"I think it's fascinating because it's always an interesting dynamic with your parents," Sheppard tells E! News. "They're the people who installed the buttons so they know exactly how to push them. Crowley's problem is that this is Fergus' mother, and he's never really accepted Fergus as him, if that makes sense. It's not Crowley's mother, but she still has a profound effect on him."

But just as Supernatural fans were taken aback when Rowena first revealed she was Crowley's mother, so was Sheppard.

"When I first heard about the story, I thought was it going to be strange," Sheppard says. "I was very curious as to how it was going to play out. Ruth is just fantastic. And the twist is that 'son of a witch' is a joke we've had for a very long time. Crowley's mother as a witch is a very scary proposition. As all Supernatural fans know, it never ends well with witches."