Jay

• Played by: Barry Bostwick
• Appears in: 4.12 Criss Angel Is A Douchebag

When he was young, Jay was a card cheat. Charlie The Magician took him under his wing and trained him to be a magician. Along with their friend Vernon they used to be very successful but now they are past their prime. Depressed at being unable to compete with the younger magicians, he decides to kill himself by undertaking a trick - the Table of Death - with the intention of letting it kill him. But he pulls of the trick, and it seems that he has regained his old talent. But when he tries another dangerous trick and another rival magician dies. Sam and Dean confront him and accuse him of using real magic. Jay has them arrested, but when he performs the Table of Death again and Charlie dies, he realises that Sam and Dean may be right.

At the theatre a young man appears and reveals himself to be Charlie. He has an enchanted pack of Tarot cards that gives him immortality. He offers eternal life to Vernon and Jay - although it means Sam and Dean will have to die. However Jay pickpockets Charlies deck of cards, leaving one with Charlie, and then stabs himself, killing Charlie.