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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 (2000); 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 The New York Times review of the film, critic Stephen Holden writes: "Both Mr. Gyllenhaal make this anguished love story physically palpable. Ledger magically and mysteriously disappears beneath the skin of his lean, sinewy character.
Shortly after the release of Candy, Ledger was invited to join the Academy of Motion Picture Arts and Sciences.
As one of six actors embodying different aspects of the life of Bob Dylan in the 2007 film I'm Not There, directed by Todd Haynes, Ledger "won praise for his portrayal of 'Robbie [Clark],' a moody, counter-culture actor who represents the romanticist side of Dylan, but says accolades are never his motivation".
Ledger received numerous posthumous accolades for his critically acclaimed performance in the film, including the Academy Award for Best Supporting Actor, a Best Actor International Award at the 2008 Australian Film Institute Awards (for which he became the first actor to win an award posthumously), Ledger was born in Perth, Western Australia, the son of Sally Ledger (née Ramshaw), a French teacher, and Kim Ledger, a racecar driver and mining engineer whose family established and owned the Ledger Engineering Foundry.
A few months before his death, Ledger had finished filming his performance as The Joker in The Dark Knight.
His death occurred during editing of The Dark Knight and in the midst of filming his last role as Tony in 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.
Ledger had aspirations to become a film director and had made some music videos, which director Todd Haynes praised highly in his tribute to Ledger upon accepting the ISP Robert Altman Award, which Ledger posthumously shared, on 23 February 2008.