Jake Gyllenhaal filmography character, a "sullen" and "schizophrenic" teenager, made him a cult hero. Although the film was critically acclaimed, it failed commercially. Gyllenhaal starred in the 2004 disaster film "The Day After Tomorrow", which, despite receiving mixed reviews from critics, was a commercial success at the box office. In 2005, he co-starred as Jack Twist opposite Heath Ledger in the romance drama "Brokeback Mountain". The actors portrayed two men that fall in love during a sheepherding expedition. The roles earned both Gyllenhaal and Ledger critical acclaim and Academy Award nominations. That same year, he starred in the drama films "Jarhead" and "Proof".
Heath Ledger 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 played the Joker in Christopher Nolan's 2008 film "The Dark Knight", which was released nearly six months after his