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Audrey Kathleen Ruston Hepburn
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Audrey Kathleen Ruston Hepburn

Three months after the birth of her son, Sean, in 1960, Hepburn began work on Blake Edwards' Breakfast at Tiffany's (1961), a film very loosely based on the Truman Capote novella. The film was drastically changed from the original version. Capote disapproved of many changes and proclaimed that Hepburn was "grossly miscast" as Holly Golightly, a quirky New York call girl, a role he had envisioned for Marilyn Monroe. Hepburn's portrayal of Golightly was adapted from the original: "I can't play a hooker," she admitted to Marty Jurow, co-producer of the film.
Despite the lack of sexual innuendo in her character, her portrayal was nominated for the 1961 Academy Award for Best Actress and became an iconic character in American cinema. Often considered her defining role, Holly Golightly, Hepburn's high fashion style and sophistication within the film became synonymous with her. She named the role "the jazziest of my career" yet admitted that, "I'm an introvert. Playing the extroverted girl was the hardest thing I ever did." The little black dress which is worn by Hepburn in the beginning of the film is cited as one of the most iconic items of clothing in the history of the twentieth century and perhaps the most famous little black dress of all time.
Playing opposite Shirley MacLaine and James Garner, her next role in William Wyler's lesbian-themed drama The Children's Hour (1961) saw Hepburn and MacLaine play teachers whose lives become troubled after a student accuses them of being lesbians. The film was one of Hollywood's earliest treatments of the subject of lesbianism, and perhaps due to the illiberal state of society, the film and Hepburn's performance went seemingly unnoticed both critically and commercially. Bosley Crowther of The New York Times, however, noted that "it is not too well acted" with the exception of Hepburn who "gives the impression of being sensitive and pure" of its "muted theme" while Variety magazine also complimented Hepburn's "soft sensitivity, marvellous projection and emotional understatement" adding that Hepburn and MacLaine "beautifully complement each other."
Her only film with Cary Grant came in the comic thriller Charade (1963). Hepburn, who plays Regina Lampert, finds herself pursued by several men who chase the fortune her murdered husband had stolen. The role earned her third and final competitive BAFTA Award and accrued another Golden Globe nomination though critic Bosley Crowther was less kind: "Hepburn is cheerfully committed to a mood of how-nuts-can-you-be in an obviously comforting assortment of expensive Givenchy costumes." Grant (59 years old at the time), who had previously withdrawn from the starring male lead roles in Roman Holiday and Sabrina, was sensitive about the age difference between Hepburn (at age 34) and him, making him uncomfortable about the romantic interplay. To satisfy his concerns, the filmmakers agreed to change the screenplay so that Hepburn's character would be the one to romantically pursue his. Grant, however, loved to humour Hepburn and once said, "All I want for Christmas is another picture with Audrey Hepburn."

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