After sitting for early graduation exams at 16, Ledger left school to pursue an acting career. With Trevor DiCarlo, his best friend since he was 3, Ledger drove across Australia from Perth to Sydney, returning to Perth to take a small role in Clowning Around (1992), the first part of a two-part television series, and to work on the TV series Sweat (1996), in which he played a gay cyclist. From 1993 to 1997, Ledger also had parts in the Perth television series Ship to Shore (1993); in the short-lived Fox Broadcasting Company fantasy-drama Roar (1997); in Home and Away (1997), one of Australia's most successful television shows; and in the Australian movie Blackrock (1997), his feature film debut. In 1999, he starred in the teen comedy 10 Things I Hate About You and in the acclaimed Australian crime movie Two Hands, directed by Gregor Jordan.
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 2001, he won a ShoWest Award as "Male Star of Tomorrow".
Ledger received "Best Actor of 2005" awards from both the New York Film Critics Circle and the San Francisco Film Critics Circle for his performance in Brokeback Mountain, in which he plays Wyoming ranch hand Ennis Del Mar, who has a love affair with aspiring rodeo rider Jack Twist, played by Jake Gyllenhaal. He also received a nomination for Golden Globe Best Actor in a Drama and a nomination for Academy Award for Best Actor for this performance, making him, at age 26, the ninth youngest nominee for a Best Actor Oscar. In The New York Times review of the film, critic Stephen Holden writes: "Both Mr. Ledger and Mr. Gyllenhaal make this anguished love story physically palpable. Mr. Ledger magically and mysteriously disappears beneath the skin of his lean, sinewy character. It is a great screen performance, as good as the best of Marlon Brando and Sean Penn." In a review in Rolling Stone, Peter Travers states: "Ledger's magnificent performance is an acting miracle. He seems to tear it from his insides. Ledger doesn't just know how Ennis moves, speaks and listens; he knows how he breathes. To see him inhale the scent of a shirt hanging in Jack's closet is to take measure of the pain of love lost."
After Brokeback Mountain, Ledger costarred with fellow Australian Abbie Cornish in the 2006 Australian film Candy, an adaptation of the 1998 novel Candy: A Novel of Love and Addiction, as young heroin addicts in love attempting to break free of their addiction, whose mentor is played by renowned Australian actor Geoffrey Rush; for his performance as sometime poet Dan, Ledger was nominated for three "Best Actor" awards, including one of the Film Critics Circle of Australia Awards 2006, which both Cornish and Rush won in their categories. A couple of weeks 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." Posthumously, on 23 February 2008, he shared the 2007 Independent Spirit Robert Altman Award with the rest of the film's ensemble cast, its director, and its casting director.
In his penultimate film performance, Ledger plays the Joker in The Dark Knight, directed by Christopher Nolan, the sequel to the 2005 film Batman Begins, first released, in Australia, on 16 July 2008, nearly six months after his death. While still working on the film, in London, Ledger told Sarah Lyall, in their interview published in the New York Times on 4 November 2007, that he viewed The Dark Knight's Joker as a "psychopathic, mass murdering, schizophrenic clown with zero empathy." To prepare for the role, Ledger told Empire, "I sat around in a hotel room in London for about a month, locked myself away, formed a little diary and experimented with voices — it was important to try to find a somewhat iconic voice and laugh. I ended up landing more in the realm of a psychopath — someone with very little to no conscience towards his acts"; after reiterating his view of the character as "just an absolute sociopath, a cold-blooded, mass-murdering clown," he added that Nolan had given him "free rein" to create the role, which he found "fun, because there are no real boundaries to what The Joker would say or do. Nothing intimidates him, and everything is a big joke." For his work in The Dark Knight, Ledger has received several posthumous award nominations and won some of these awards.
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 The Imaginarium of Doctor Parnassus.
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.
In 2006 Ledger directed music videos for the title track on Australian hip-hop artist N'fa's CD debut solo album Cause an Effect and for the single "Seduction Is Evil (She's Hot)".
Later that year, Ledger inaugurated a new record label, Masses Music, with singer Ben Harper and also directed a music video for Harper's song "Morning Yearning".
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. Ledger created and acted in a music video set to Drake's recording of the singer's 1974 song about depression "Black Eyed Dog"–a title "inspired by Winston Churchill’s descriptive term for depression" (black dog); it was shown publicly only twice, first at the Bumbershoot Festival, in Seattle, Washington, held from 1 September to 3 September 2007; and secondly as part of "A Place To Be: A Celebration of Nick Drake", with its screening of Their Place: Reflections On Nick Drake, "a series of short filmed homages to Nick Drake" (including Ledger's), sponsored by American Cinematheque, at the Grauman's Egyptian Theatre, in Hollywood, on 5 October 2007. After Ledger's death, his music video for "Black Eyed Dog" was shown on the internet and excerpted in news clips distributed via YouTube.
He was also working with Scottish screenwriter and producer Allan Scott on an adaptation of the 1983 novel The Queen's Gambit, by Walter Tevis; he was planning both to act in and to direct it, and it would have been his first feature film as a director.
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