There are screen icons, and then there's Audrey Hepburn. One of the most beautiful faces to grace the silver screen, Hepbrun gained international prominence with her Oscar-winning role in 1953's Roman Holiday. What followed was a successful career full of critical and commercial hits that cemented her legacy as one of classic Hollywood's biggest stars.
Revered for her acting abilities and status as a fashion icon, Hepburn was named the third greatest female icon of Hollywood's Golden Age by the American Film Institute. Her career spanned over four decades, including multiple films that have become timeless classics.
10 'How to Steal a Million (1966)
Hepburn and Peter O'Toole star in William Wyler's 1966 heist comedy How to Steal a Million. The plot centers on a young woman who hires an infamous cat burglar to steal a precious artwork forged by her father and accidentally exhibited at a prestigious museum.
A playful and stylish heist comedy elevated by the now-legendary talent of its two leads, How to Steal a Million is fun and light. Dressed head to toe in stunning Givenchy outfits, Hepburn is a vision of charm and grace. The film further proves what an inspired pairing Wyler and Hepburn were, crafting an endlessly entertaining crime comedy that has stood the test of time.
9 'The Nun's Story (1959)
Fred Zinnemann's 1959 drama The Nun's Story stars Hepburn alongside Peter Finch and Peggy Ashcroft. The plot follows Gabrielle van der Mal, who abandons her upper-class existence to become a nun, working as a nurse in Belgian Congo. When the Nazis kill her father, she doubts her calling and struggles to maintain her mandated neutrality.
A safe and occasionally preachy film, The Nun's Story is held high by Hepburn's stellar performance in the lead role. As Sister Like, Hepburn is gentle and luminous, delivering one of her brightest and most irresistible big-screen turns, resulting in her third Oscar nomination.
8 'Funny Face' (1957)
Stanley Donen's 1957 musical rom-com Funny Face sees Hepburn starring opposite Fred Astaire. Loosely based on the 1927 eponymous musical, the plot follows a fashion photographer who discovers a shy bookstore employee and believes she can become a model. The two travel to Paris, where they fall in love.
Funny Face was one of the early films that cemented Hepburn's status as a modern fashion icon. The imagery of the beautiful actress against several Parisian backgrounds has become iconic, even if the film's songs and plot have fared worst. Still, Hepburn remains winning, a bright and lovely ray of sunshine lighting the film and turning it into one of the best musicals from Holywood's Golden Age.
7 'Wait Until Dark (1967)
Hepburn stepped out of her comfort zone with Terrence Young's 1967 psychological thriller Wait Until Dark. The plot follows a blind woman harassed by two violent criminals looking for a doll full of heroin her husband inadvertently acquired.
A massive commercial hit, Wait Until Dark features one of Hepburn's ballsiest performances, even if she maintains the sweet and unassuming persona that made her a star. The actress is the living, breathing embodiment of terror and anxiety in a nail-biting thriller that exploits its premise to the fullest. Hepburn's work is inspired, earning her last Oscar nomination and immediately standing out among her filmography for its chilling effectiveness.
6 'Two for the Road' (1967)
Albert Finney stars opposite Hepburn in the 1967 romantic comedy-drama Two for the Road. The plot centers on a married couple whose relationship has deteriorated over the years. As they travel to the French Riviera for a holiday, they reminisce about their romance's early days, pondering all they lost along the way.
Two for the Road contains arguably Hepburn's most mature and comprehensive performance. The actress plays a fully-fledged character, going through numerous emotions and grounding them firmly in humor and reliability. The film expertly balances romance and comedy, cynicism and hope, largely thanks to Hepburn's innate ability to walk the fine line.
5 'Sabrina' (1954)
Hepburn worked twice with Billy Wilder, one of the most iconic directors of Hollywood's Golden Age. Sabrina is the strongest of their two collaborations, with Hepburn starring in the titular role opposite Humphrey Bogart and William Holden. The plot centers on a young woman who grabs the attention of a wealthy playboy and his more serious older brother.
Hepburn received her second Oscar nomination for the role and cemented her place as one of the loveliest leading ladies in romantic comedy history. A modern and lively Cinderella, Hepburn is mesmerizing in the now-idolized role, balancing allure with naiveté like few other actresses could. Sabrina is charming and enchanting, a triumph of the rom-com featuring one of Hepburn's most effortless performances.
4 'My Fair Lady' (1964)
George Cukor and Audrey Hepburn worked together only once in the 1964 musical My Fair Lady. Based on the eponymous stage musical, the film centers on Professor Higgins, who boldly proclaims he can turn Cockney flower seller Eliza Doolittle into a high society lady in Edwardian London.
My Fair Lady is a timeless classic and one of the all-time best movie musicals. Much has been said about Hepburn's Cockney accent and inability to sing the score, which resulted in Marni Nixon dubbing her. However, Hepburn remains a triumphant presence, single-handedly making the film soar even as it battles between reinforcing and combatting sexist themes. Hepburn's Eliza Doolittle is a silver-screen legend, an instantly recognizable character that has stood the test of time.
3 'Charade' (1963)
Cary Grant and Audrey Hepburn made one of the all-time great big-screen couples in Stanley Donen's 1963 screwball mystery rom-com Charade. The plot follows Regina Lampert, a recently-widowed woman who meets the dashing but mysterious Peter Joshua as they chase three men pursuing a fortune stolen by her late husband.
Thrilling, clever, hysterical, and devastatingly romantic, Charade is a genre-blending masterpiece. Hepburn is reliably charming as Regina, but she brings an unusual grittiness to the role, even as she stays two steps behind Grant's character throughout the plot. Elevated by Henry Mancini's now-legendary score and with one of the cleverest screenplays of the 1960s, Charade is an incredible mystery comedy that's often been imitated but never replicates.
2 'Breakfast at Tiffany's' (1961)
Breakfast at Tiffany's remains a beloved classic, and Holly Golightly is arguably Audrey Hepburn's most iconic. From the moment she steps out of the cab into the misty morning of 1960s New York, Hepburn is a vision of melancholy and glamour, a broken dream in high heels and a tiara.
Breakfast at Tiffany's is a gloomy drama disguised as a rom-com, and Hepburn understands it, delivering one of her more nuanced portrayals. She disguises Holly's pain behind dreamy eyes and fancy clothes, hinting only at it through stolen glances and dreamy looks at a distant and elusive future. Hepburn received her fourth Oscar nomination for Breakfast at Tiffany's and solidified her place as a Golden Age legend while also cementing herself as a timeless fashion icon.
1 'Roman Holiday (1953)
Hepburn's ticket to stardom came courtesy of William Wyler's 1953 rom-com Roman Holiday. The actress stars as Ann, the princess of an unnamed European country who escapes her security detail to spend some much-deserved leisure time in Rome. She is joined by Joe, a reporter looking for an exclusive with the free-spirited princess, and an unexpected romance blossoms as they spend time together.
Roman Holiday is famous for its bittersweet ending and for giving Hepburn her only competitive Oscar win. The actress is a revelation as the young and enchanting Princess Ann, delivering an earnest, unassuming yet commanding and assured performance that remains a high point in romantic comedies. Roman Holiday might not end with two lovers united, but it exists as a lover letter to those romance stories that might be short but no less meaningful.