When Dean Winchester is sent to Hell at the end of the third season,[REF] it is the demon Alastair who tortures him, stopping only when he eventually convinces Dean to torture other souls himself [REF].
Alastair (Mark Rolston) makes his debut in the episode "I Know What You Did Last Summer", in which he seeks to capture and interrogate Anna Milton, a fallen angel who can still hear the conversations of other angels.