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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After Ledger's death, in response to some press reports about his will, filed in New York City on 28 February 2008, and his daughter's access to his financial legacy, his father, Kim Ledger, said that he considered the financial well-being of Heath's daughter Matilda Rose an "absolute priority", whilst also stating that her mother, Michelle Williams, was "an integral part of our family". He added, "They will be taken care of and that's how Heath would want it to be". Some of Ledger's relatives may be challenging the legal status of his will signed in 2003, prior to his involvement with Williams and the birth of their daughter and not updated to include them, which divides half of his estate between his parents and half among his siblings; they claim that there is a second, unsigned will, which leaves most of that estate to Matilda Rose. Williams' father, Larry Williams, has also joined the controversy about Ledger's will as it was filed in New York City soon after his death.
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In their New York Times interview, published on 4 November 2007, Ledger told Sarah Lyall that his recently completed roles in I'm Not There (2007) and The Dark Knight (2008) had taken a toll on his ability to sleep: "Last week I probably slept an average of two hours a night. ... I couldn't stop thinking. My body was exhausted, and my mind was still going." At that time, he told Lyall that he had taken two Ambien pills, after taking just one had not sufficed, and those left him in "a stupor, only to wake up an hour later, his mind still racing".