Crowley plays a key role on the Supernatural episode "Two Minutes to Midnight." In this scene from it, he makes Bobby admit something major to Sam and Dean.
Added:
The season finale of Supernatural is creeping closer, and this episode takes a major step in that direction. It features a dangerous deal for Dean and is titled "Two Minutes to Midnight."
Added:

Supernatural Season 5 Episode 21 Quotes

World's gonna end, seems silly to get all precious over one little soul.

Bobby

Bobby: Why'd you take a picture?
Crowley: Why'd you have to use tongue?