4. Breakfast At Tiffany's (1961)
The hair. The dress. The glasses. "How do I look?" It's as iconic as anything in her repertoire and the mysterious allure of Holly Golightly remains even to this day. Emerging from a novella by noted author Truman Capote,
Breakfast At Tiffany's isn't a perfect film - namely the extremely uncomfortable sight of Mickey Rooney caricaturised as a deeply offensive and racist Japanese stereotype. But there is a hell of a lot to love here - Hepburn is in her element here, eschewing most of her earlier film's sweetness in favour of a cool-as-ice confidence hiding a frightened and lonely young woman who's finding her career path isn't exactly what she wants anymore. George Peppard is an ideal leading man opposite her, the path of their characters' journeys from world-weariness into hopefulness a perfect path for the viewer to become absorbed in. We'll never look at a pastry and coffee breakfast or a rainy alleyway the same again.