|“||Nothing is permanent, not even death.||„|
|~ Tony Shepard|
Anthony "Tony" Shepard is the main antagonist of Terry Gilliam's 2009 fantasy film The Imaginarium of Doctor Parnassus. He is a suave con artist who attempts to use a traveling show as a vehicle for fame and fortune.
Tony was portrayed by the late Heath Ledger (who also portrayed The Joker in The Dark Knight) in his second and final villainous role, and overall, his final film role before his death in January 22, 2008. Following Ledger's death during production, three actors played the character when transformed by the Imaginarium:
- Johnny Depp (who also portrayed Gellert Grindelwald in Fantastic Beasts and Where to Find Them, Sweeney Todd in Sweeney Todd: The Demon Barber of Fleet Street and The Wolf in Into the Woods)
- Jude Law (who also portrayed Harlen Maguire in Road to Perdition, Pitch Black in Rise of the Guardians and Vortigern in King Arthur: The Legend of the Sword)
- Colin Farrell (who also portrayed Bullseye in Daredevil, Bobby Pellitt in Horrible Bosses, Jerry Dandridge in Fright Night, and Gellert Grindelwald's disguise of Percival Graves in Fantastic Beasts and Where to Find Them).
Doctor Parnassus' theatre troupe finds Tony drowning in a river; after they poull him out, he spits up a golden pipe. he claims to have amnesia, and they take him in a carnival barker. He convinces the troupe to put on a more modern show, with him as its star.
Tony finds out about a bet that Doctor Parnassus has with Old Nick, a Satanic trickster, in which the first one to claim five souls takes possession of Valentina. Tony offers to help in return for Parnassus teaching him his magical tricks. Parnassus refuses at first, but relents out of fear of losing his daughter.
During a show, he invites a wealthy old woman into the Imaginarium, where his face changes shape and he romances her, dancing with her and taking her on a gondola ride, and in the process wins her soul away fro Old Nick. The woman, smitten, gives him a large check. He does the same with three other wealthy older women, bringing in vast sums of money. He also romances Doctor Parnassus' daughter, Valentina, frustrating her fellow troupe member and true love Anton.
Russian gangsters to whom Tony owes money chase him into the Imaginarium, but he escapes. He offers to give Doctor Parnassus his soul in exchange for the power to control the dream world within the Imaginarium. He tries to entice Valentina into the Imaginarium, but Anton blocks their way and fights Tony, while revealing that Tony has defrauded dozens of people through a series of fake charities. Tony pushes Anton into the Imaginarium and follows him in with Valentina.
In the dream world, Tony (whose face has once again changed) is speaking before a posh fundraiser. Anton interrupts him and exposes his fraud, and the angry crowd chases Tony to a gallows. Smitten with Tony and angry at her father, Valentina gives her soul to Old Nick; he thus wins the bet. disappointed with the easy victory, Old Nick offers to trade Valentina for Tony; Parnassus agrees. Parnassus confronts Tony at the gallows holding Tony's golden pipe and a fake. he challenges Tony to pick the real pipe for his life. Tony picks one and Parnassus swallows it and then hangs himself, Tony then makes Parnassus spit it out believing is the real one, he then swallows it and lets the people hang him, however Parnassus wakes up and reveals to Shepard that the real pipe was inside his throat all along, Tony watches in horror as the people hang him and the fake pipe breaks inside his throat, letting the rope hang him and kill him for good.