From 2000 to 2005, he starred in supporting roles as Gabriel Martin, the eldest son of Benjamin Martin (Mel Gibson), in The Patriot (2000), and as Sonny Grotowski, the son of Hank Grotowski (Billy Bob Thornton), in Monster's Ball (2001); and in leading or title roles in A Knight's Tale (2001), The Four Feathers (2002), The Order (2003), Ned Kelly (2003), Casanova (2005), The Brothers Grimm (2005), and Lords of Dogtown (2005). In 2001, he won a ShoWest Award as "Male Star of Tomorrow".
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In his penultimate film performance, Ledger played the Joker in Christopher Nolan's 2008 film The Dark Knight, which was released nearly six months after his death. While working on the film in London, Ledger told Sarah Lyall in their New York Times interview that he viewed The Dark Knight's Joker as a "psychopathic, mass murdering, schizophrenic clown with zero empathy". For his work on The Dark Knight, Ledger posthumously won the Academy Award for Best Supporting Actor, which his family accepted on his behalf, as well as numerous other posthumous awards, including the Golden Globe Award for Best Supporting Actor, which Christopher Nolan accepted for him. At the time of his death on 22 January 2008, Ledger had completed about half of the work for his final film performance as Tony in Terry Gilliam's The Imaginarium of Doctor Parnassus. Gilliam chose to adapt the film after his death by having fellow actors Johnny Depp, Jude Law, and Colin Farrell play "fantasy transformations" of his character so that Ledger's final performance could be seen in theatres.