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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.
In his penultimate film performance, Ledger played the Joker in Christopher Nolan's 2008 film The Dark Knight, 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 For his work on The Dark Knight, Ledger won the Academy Award for Best Supporting Actor with his family accepting it 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 a news conference at the 2007 Venice Film Festival, Ledger spoke of his desire to make a documentary film about the British singer-songwriter Nick Drake, who died in 1974, at the age of 26, from an overdose of an antidepressant.