20. Green Mansions (1959)
This exotic MGM romance directed by Hepburn’s husband, Mel Ferrer, was actually her first big flop. Anthony Perkins plays a Venezuelan refugee whose life is saved by Rima the Jungle Girl: Hepburn in a suede pixie tunic, accessorized with a pet fawn and backed by a brownface supporting cast.
19. Bloodline (1979)
Hepburn was now really too mature for that kind of ingenuous role; in a trashy Sidney Sheldon adaptation, she inherits a pharmaceutical empire and finds herself under threat across Europe. Not as fun as it sounds, but offsets include a cast of suspects and a score from Ennio Morricone.
18. They All Laughed (1981)
Hepburn was last given the lead in Peter Bogdanovich’s lighthearted indie-style romantic comedy. There’s an hour of Ben Gazzara following her through the streets of New York before she even hears her speak, and the film was scuttled by the murder of poor Dorothy Stratten, one of Hepburn’s co-stars.
17. The Unforgivables (1960)
A Texas rancher’s daughter turns out to be a Kiowa, leading to friction between her adoptive family, local fanatics, and the tribe demanding her return. Hepburn is fundamentally misinterpreted as a Native American in John Huston’s dark western; even worse, she broke her back in a serious riding accident during production.
16. Always (1989)
Hepburn, in a dazzling white cable-knit, is literally heaven in Steven Spielberg’s remake of A Guy Named Joe, a movie that’s sure to have you blushing. The star’s final movie appearance was little more than a cameo, but what a cameo! Bonus points for donating his entire $1 million salary to Unicef.
15. Children’s Hour (1961)
Well-meaning but dated melodrama adapted from Lillian Hellman’s play, These Three, about two schoolteachers (played by Hepburn and Shirley MacLaine) whose lives are ruined when a student spreads the rumor that they are lesbians. “The reason I chose Audrey is because she’s so clean and healthy,” said director William Wyler. “I don’t want boobs in there.”
14. Love in the Afternoon (1957)
Hepburn plays the cellist daughter of a private detective who charms a millionaire playboy in Billy Wilder’s elegant Lubitsch-esque romantic comedy set in Paris. But the 27-year age gap between the leads, exacerbated by Gary Cooper already showing signs of his terminal illness, proved baffling even to contemporary viewers.
13. My Fair Lady (1964)
Julie Andrews fans were furious when the Broadway original Eliza Doolittle was snubbed by the film’s producers, but Hepburn is a charming cockney and looks fabulous in Cecil Beaton costumes. His songs had to be dubbed, although co-star Rex Harrison was allowed to sprechstimme his way through the musical numbers.
12. War and Peace (1956)
King Vidor’s literary epic, set in Italy, may not be the best adaptation of Tolstoy’s novel, but it has a fine score by Nino Rota and fine cinematography by Jack Cardiff. The script is clunky and the acting is a hodgepodge of opposing styles, but Hepburn gives a light performance as Natasha.
11. Sabrina (1954)
Hepburn is enchanting as the chauffeur’s daughter in love with the son of her father’s employers. Humphrey Bogart plays the brother who tries to sabotage this match by wooing her for himself, but the 29-year age gap between them means Wilder’s rom-com looks a bit gross in hindsight.
10. Breakfast at Tiffany’s (1961)
Truman Capote envisioned Marilyn Monroe as the heroine of his short story, but the watered-down film role went to Hepburn, whom Photoplay called “utterly un-Marilyn Monroeish.” The Japanese cartoon of Mickey Rooney is a shocker, and I’ll never forgive Holly for throwing her cat in the rain, but Hepburn is an icon of timeless chic in her Givenchy little black dress.
9. Paris When It Sizzles (1964)
Hepburn plays a typist hired to help a screenwriter (William Holden) meet his deadline in a deconstruction of cinematic cliches that was canceled upon release. George Axelrod, the Charlie Kaufman of his day, wrote the screenplay, which is full of jokes, genre riffs and superstar cameos, and Hepburn is surprisingly funny and sexy as a comic femme fatale.
8. How to Steal a Million (1966)
What a treat to see Hepburn hiding in a closet with a leading man suitable for his age. Peter O’Toole plays the debonair burglar whom she enlists to help her steal a fake Cellini statuette. Wyler’s pretty Parisian hug doesn’t quite reach the heights of Charade, which it’s clearly modeled after, but it’s worth a look for ultra-mod Givenchy outfits and Audrey’s charlady costume.
7. The Nun’s Story (1959)
Hepburn’s best performances are those where she doesn’t appear to be playing, but the culmination of her self-consciously “serious” work is the title role in Fred Zinnemann’s film about a Belgian nun whose faith is tested by various ways through nursing in the Congo. , the handsome but agnostic doctor of Peter Finch, and the Nazi occupation of Belgium.
6. Wait for the Night (1967)
Hepburn plays a blind woman in this tense thriller that never quite transcends its stage origins. Alan Arkin stars as the villain trying to get his hands on a heroin-stuffed doll in his possession while dressing up in goofy disguises.
5. Two for the Road (1967)
In a turning point for the books, Hepburn is seven years older than Albert Finney, the actor chosen as her husband here. She swaps Givenchy for groovy Carnaby Street outfits in Stanley Donen’s clever relationship drama, cleverly scripted by Frédéric Raphael, about an unhappy married couple driving south through France, with flashbacks showing the couple making the same trip in happier times.
4. Roman Holiday (1953)
“She was absolutely enchanting, and we said ‘That’s the girl! Princess Ann is so fed up with official duties that she travels to Rome with American journalist Gregory Peck (only 13 years older than Hepburn), rides a Vespa and gets a childish haircut.
3. Robin and Marianne (1976)
A reunion of middle-aged movie legends; Hepburn is practically the same age as Sean Connery, his love for the bittersweet coda of Richard Lester’s Robin Hood. The good Marian is now an abbess, still angry that Robin abandoned her to go galloping to the crusades. Everyone is older but not necessarily wiser in this ironic and elegiac romance with a heartbreaking ending.
2. Funny Face (1957)
Hepburn plays a bluestocking bookseller who gets a chic makeover (although she looks perfectly chic to begin with) in Donen’s delightful musical. Fred Astaire, 30 years older than his leading lady, though still nimble on his pins, plays the Avedon-esque photographer who takes her to Paris for a fashion shoot. And the music is great: Think Pink! Hello Paris ! Basal metabolic rate!
1. Charades (1963)
It’s the best Hitchcock movie Hitchcock has ever made: Donen’s flawless romantic thriller stars Hepburn, dressed in Givenchy, at her most adorable, with Cary Grant (25 years her senior, but hey, it’s Cary Grant!) as the mysterious, suave man who saves her from MacGuffin’s Huntsman Thugs. No one flees for their life as beautifully as Audrey, and Paris has never looked better.