Won: Five Oscars, including Best Supporting Actress (Cate Blanchett), 2005 Martin Scorsese's The Aviator won five of the eleven Oscars it was nominated for at the 2005 awards, including one for Cate Blanchett (nominated this year for her work in Carol), who won her first Academy Award on the night (she has triumphed again since, for Woody Allen's Blue Jasmine). The rest of The Aviator's wins were for technical achievement (Editing, Cinematography, etc.), with the film missing out on some of the bigger awards that were probably expected of it (Picture, Director). Still, the film is one of Scorsese's best post-Goodfellas, helmed admirably by Leonardo DiCaprio, the actor here nominated for his performance as Howard Hughes in the director's and star's second collaboration together, after Gangs Of New York. As an interesting bit of side trivia, Blanchett plays Katharine Hepburn in The Aviator, making her the only person to win an Oscar for playing another Oscar winner (Hepburn won four Best Actress Oscars in her career , marking her out as the most rewarded performer ever).