Friday, July 11, 2025

Ranking the Films of Audrey Hepburn

 

1. Roman Holiday (1953)

It had been at least a decade since I'd watched this, so I didn't remember just how good it is. Perhaps the most honestly, realistically sad ending to a romantic comedy that doesn't involve anyone dying of cancer. The age gap between leads, which somehow becomes only more exaggerated as Audrey's career goes on, is also at its least objectionable here; roughly a decade of difference isn't so dramatic, and feels right in line with the way the characters meet, fall for each other, and ultimately part. Of course this is how it happens: this was always how it was going to happen. One of my favorites of all time.
 
Rating: 5 out of 5 
 
Audrey's Look: Audrey spends the bulk of the movie dressed like Elizabeth from BioShock Infinite, which is fine by me, but the iconic haircut scene defines her vibe for the rest of the film.
 
The Age Gap 
Audrey Hepburn = 23
Gregory Peck = 36
 
 

4. Sabrina (1954)

I've seen this a few times before but it never left much of an impression on me. I gained a newfound appreciation for it on this latest viewing, however. It's actually quite funny, and while the romance never exactly feels perfectly true, it isn't difficult to understand how walking corpse Humphrey Bogart could find himself in a lot of trouble. "I'm about to make an ass of myself with a girl of twenty-two. Look at me! Joe College with a touch of arthritis."
 
Rating: 4 out of 5 
 
Audrey's Look: The second time in two movies that Audrey gets a haircut to symbolize her maturation from girl to woman, but it just doesn't hit the same this time. She goes through a lot of wardrobe changes after graduating French finishing school, each more stylish than the last. 
 
The Age Gap 
Audrey Hepburn = 24
Humphrey Bogart = 53
 
 

14. War and Peace (1956)

I can't even complain about this movie being three and a half hours long because it's War and Peace; there was a whole running joke in the Peanuts New Year's special about how long the book is. While the runtime did make it kind of a slog to get through, I can't say that I was actually bored watching it. But I had to stop about two hours in and didn't have an opportunity to finish watching it until a week later, by which point I had forgotten who most of the secondary characters were (except Napoleon Bonaparte, of course). Henry Fonda's weak-willed, indecisive male lead was an interesting choice for the romantic hero, but Audrey gets top billing and whenever she wasn't on screen I kept wondering "Where's Audrey?" I didn't hate it but I can't imagine ever wanting to watch it again.
 
Rating: 3 out of 5 
 
Audrey's Look: The first time you see her in the opening scene, sitting in that window wearing that yellow dress, you could have knocked me over with a feather.
 
The Age Gap 
Audrey Hepburn = 26
Henry Fonda = 50 
 
 

11. Funny Face (1957) 

"Oh, how could I be a model? I have no illusions about my looks; I think my face is funny." I have to imagine they didn't know they were writing for Audrey Hepburn when they turned in the script. After she was cast, maybe someone should have suggested not giving that line to the most beautiful woman who ever lived. They don't even try to She's All That her by giving her glasses or something, she just looks like Audrey Hepburn from scene one. If possible, she looks less attractive after the dramatic makeover scene. Otherwise, a bare-bones but inoffensive plot; only 103 minutes but it still feels overly long, because so much of that time is spent on pointless songs and dance sequences. That's what the people came for, I guess, but I just wanted to spend more time with Audrey working at the bookstore.
 
Rating: 3 out of 5 
 
Audrey's Look: She plays a fashion model so there are a lot of costume changes in this one, but the best is the shapeless potato sack she wears while working as a shop clerk. I love her hair in this scene, she's so cute I want to slit my throat. 
 
The Age Gap 
Audrey Hepburn = 27
Fred Astaire = 57 
 

12. Love in the Afternoon (1957)

"He was gay, Gary Cooper?" Mixed feelings about this one. It started out strong enough; this was John McGiver's feature film debut and he's hilarious in this movie. But by around the seventy-minute mark, when Audrey runs into Gary Cooper at the opera a year after they last met and he doesn't remember her, I was ready for it to be over. Most of the remaining hour dragged until Gary Cooper hired private eye Maurice Chevalier to discover Audrey's identity, not knowing that Chevalier was her father. The scene where he recognizes the true nature of the man and pleads with Cooper to let her go was quite powerful and had me hopeful for a bittersweet downer ending where Cooper's character does the first decent thing of his life and leaves her at the train station. Alas, they chickened out and went with an unearned romantic ending that soured the whole film for me. 
 
Rating: 3 out of 5
 
Audrey's Look: Her hairstyle in this film is adorable, but her character feels so much younger even than Audrey herself actually was at the time that it's kind of gross seeing her with Cooper's lecherous playboy soda magnate. She looks like a high school girl on a date with her grandfather. They should have given Gary Cooper The Substance before filming his scenes. 
 
The Age Gap
Audrey Hepburn = 27
Gary Cooper = 56 
 
 

15. Green Mansions (1959) 

Strange film where Audrey plays a savage jungle girl with great hair and perfectly manicured nails. She spends so much of the middle part of the film aimlessly frolicking through a Hollywood soundstage real South American jungle with Norman Bates and a baby deer that I started wondering if this was going to be the rest of the movie. But eventually it becomes a confused retelling of the white man's lust for gold bringing ruin to paradise, except with the white man immediately abandoning his self-destructive plan to avenge his father's death when he meets a pretty girl, leaving the murderous natives to do all the ruining. Native American villain Kua-Ko is played by Spanish-Italian actor Henry Silva, who went on to play North Korean spy Chunjin in The Manchurian Candidate a few years later. What a range!
 
Rating: 2.5 out of 5
 
Audrey's Look: No costume changes this time as she spends the whole movie wearing a simple homespun muslin shift. Even dressed in rags, however, she's just too elegant and glamorous to be believable as a filthy jungle waif. This movie isn't horrible but with every decision evident on-screen you have to wonder what the hell they were thinking.
 
The Age Gap
Audrey Hepburn = 29 
Anthony Perkins = 26 (What casting director was asleep at the wheel on this one? Didn't they know the rules???)
 
 

5. The Nun's Story (1959)

Knowing nothing about this film before watching it, my biggest fear was that it was going to be a boring religious flick. It turned out to be more like a horror movie, some real Handmaid's Tale vibes. Being a nun is apparently some kind of living death. Audrey undergoes such dehumanization and depersonalization, the self-eradication of her ego, the loss of her name and voice, even the forfeiture of her own memories, that I wonder if Margaret Atwood didn't take a little inspiration from this movie when writing her book; even the titles are similar. Allowed to play a serious, dramatic role for once, Audrey gives one of her best performances. All you see of her for the whole movie is her face, and she's still luminous. And she doesn't even make out with a geriatric!
 
Rating: 4 out of 5
 
Audrey's Look: She's dressed like a nun for two and a half hours, but none of the other nuns has eyelashes like that.
 
The Age Gap
Audrey Hepburn = 28
God = ∞
 
 

16. The Unforgiven (1960)

Extremely racist anti-racism movie, with a non sequitur incest subplot thrown in for good measure. Weird and mostly awful despite generally good performances.  
 
Rating: 1.5 out of 5 
 
Audrey's Look: I hate to say it but the frontier homesteader look just doesn't suit her. It's too bad she never did a real Western; I'm sure she would have nailed the cowgirl aesthetic. As it is, Audrey's a great actress but she cannot pass as Native American, no matter how much the other characters insist how "dark" she is.
 
The Age Gap 
Audrey Hepburn = 29
Burt Lancaster = 45
 
 

3. Breakfast at Tiffany's (1961)

"There was once a very lovely, very frightened girl. She lived alone except for a nameless cat."
 
It's difficult to be objective about this movie when I've loved it as long as I've loved movies that weren't animated Disney VHS tapes in fat plastic clamshell cases. Truth be told, the book is better, both as a piece of art and as an iteration of this specific story, but that's okay; each is great in its own way and I love them both.
 
I would say that my affection for the film version peaked during my high school years. This makes sense to me, as it is in some ways a very high-school movie. I feel like a traitor saying that, but I don't mean it as a criticism. The movie strips out much of the raw pathos of the novel, not to mention its queer subtext and sexual subversiveness. In place of these are commercial melodrama and a comfortingly adolescent take on romance ("Is Holly Golightly a manic pixie dream girl?" Fuck you, who gives a shit?). 
 
The movie's wonderful, saccharine Hollywood ending plays like a cracked-mirror version of the novel's bittersweet denouement. The book leaves a knot in your stomach and a lump in your throat; the movie ends with true love conquering all, a fairy-tale kiss in the rain. It sounds trite and artificial described so simplistically, and maybe it is, but it's "a real phony," to quote O.J. Berman: it's earnest in its artificiality, if you're reductive enough to call it that.
 
Audrey steals the show, but I love the everyman earnestness of George Peppard's performance as well. His character in the novel is the unnamed narrator, a passive observer relating his experiences with a girl he once knew. He reads like a self-insert of Capote himself, a struggling writer trying to make ends meet as a gay man in 1940s New York. By contrast, Paul Varjak, now a named and active participant in the plot and definitely not gay, almost feels like a blank slate for the audience to project themselves on. I know that teenage me could hear himself in the sardonic musings of Paul's untested literary voice, could grasp the pointed deliberateness of Peppard's matter-of-fact, almost flat line delivery, his sober reticence a foil to Holly's manic energy and exaggerated diction.
 
 
Holly herself is 18 in the novel; Audrey Hepburn was 31 while playing her. The movie never gives her age, but its vague timeline suggests that she's around 20, an age that Audrey, although more beautiful than ever, clearly isn't. This discrepancy was never apparent to me while watching the movie as a teenager, but now that I'm 30 or 40 years old I can't help but notice. Audrey is wonderful in the film and I wouldn't want to see anyone else playing that role, even if the film's version of Holly reads very differently from the book's. But it's the role of a character who all signifiers indicate is very young. I can't untangle that Gordian knot, save to remember that Capote wanted Marilyn Monroe for the part and she was 34 at the time. 
 
Well, I guess it is just a movie, after all, but golly gee damn if I don't still love everything about it, apart from the horrible racist caricature.
 
Rating: 4.5 out of 5
 
Audrey's Look: The tiara is iconic but I think this soft-focus closeup is my favorite shot of her in the film:


Guys only want one thing, and it's to find a girl who looks at them the way Audrey Hepburn looks at George Peppard in Breakfast at Tiffany's.
 
The Age Gap
Audrey Hepburn = 31
George Peppard = 32

9. The Children's Hour (1961)

The heaviest and most uncomfortable entry in Audrey's filmography, with the most hateable child villain since that episode of The Twilight Zone with Billy Mumy. The movie goes to some very dark places and is emotionally aggravating to the extent of becoming hard to watch in several scenes, but part of its uncomfortableness comes from its choice not to engage with its subject matter as fully as it might have. The injustice and unfairness of how Audrey Hepburn's and Shirley MacLaine's lives are overturned by a lie heard halfway around the world is well represented, but the substance of the lie, the allegation of a lesbian affair between the two leads, feels danced around and largely unexplored. Perhaps it's because the movie was based on a play written in the 1930s, or because of production restrictions in Hollywood, but despite the subversive topic at its heart, it never felt quite as subversive as I wanted it to; it’s more about the dangers of fake news than of bigotry or homophobia. The one scene toward the end where Shirley MacLaine drags the kernel of truth inside the lie kicking and screaming into the light is the best scene in the movie.
 
Both leads deliver great performances, but Audrey's character is the more reserved and put-together of the two, leaving MacLaine to handle the most emotional heavy-lifting. Both characters struggle externally against the community that has turned on them as well as internally, but Audrey's fight is to remain true under pressure to the person she knows herself to be, while Shirley MacLaine does whatever she can to avoid confronting the truth of herself. It's a very sad and powerful movie, I just wish it had been more explicit with the ugly truths it laid bare on screen instead of being quite so squeamish about the audience's sensibilities.
 
Rating: 3.5 out of 5
 
Audrey's Look: Schoolmarmish and beside the point.
 
The Age Gap
Audrey Hepburn = 32
James Garner = 33
 

6. Charade (1963)

Another old favorite of mine, Charade is a Hitchcockian thriller crossed with a screwball romantic comedy. The resulting tone can be somewhat jumbled at times, with genuinely tense sequences like James Coburn lighting matches in Audrey Hepburn's lap in a phone booth oddly juxtaposed with the script's inopportune horniness, as Audrey spends the whole movie begging Cary Grant to have sex with her while they're running from murderers. Grant's performance ranges from hilarious to uncharacteristically flat, but the latter is likely due to his reported discomfort with the age gap between romantic leads. Overall, though, the end result is a very funny and clever film that is a great joy to watch.
 
Rating: 4 out of 5
 
Audrey's Look: Persistently lovely throughout a variety of wardrobe changes, though sadly none has really become iconic except maybe the kerchief-and-sunglasses disguise when she's "undercover," and her brand new leopard-skin pill-box hat. She plays it a lot sillier than is typical of her performances, with lots of cute bug-eyed mugging and cartoonishly exaggerated expressions of distress. Wish she had done more movies like this.
 
The Age Gap
Audrey Hepburn = 33
Cary Grant = 58
 

13. Paris When It Sizzles (1964)

One of those self-indulgent Hollywood movies about the making of self-indulgent Hollywood movies. Lightweight and insubstantial, this one at least has going for it a few good laughs delivered through random and bizarre comedic sequences, including a very funny performance by Tony Curtis. The scatter-brained plot of the movie-within-the-movie, while directly lampshaded in the film, never congeals into anything larger than the sum of its disjointed parts, save for William Holden's drunken confession of being a womanizing heel and a hack-fraud screenwriter. It makes one wonder if maybe the actual screenplay wasn't put together this way in real life, with the writer throwing everything he could think of against the wall until he hit 138 pages. Harmless but mostly unmemorable. "Did you ever realize that Frankenstein and My Fair Lady are the same story? One ends happily and the other one doesn't. Think about that next time you're in church."
 
Rating: 3 out of 5
 
Audrey's Look: Audrey rocks the Zooey Deschanel bangs better than Zooey Deschanel ever did, but her most interesting outfit in the film is the bomber pilot costume she wears during an imaginary aerial dogfight. I would have liked to see more genre-hopping like that instead of so many variations on the tiresome heist plot, but she does have those Big Magic Eyes™ everyone keeps talking about.
 
The Age Gap
Audrey Hepburn = 33
William Holden = 44
 

7. My Fair Lady (1964)

My Fair Lady has never been one of my favorite musicals so I was surprised to realize, fairly soon into the movie, how much I was enjoying it. The three-hour runtime seems formidable, but it has an intermission, as all socially acceptable movies of a certain length do, and avoids the feeling of being rushed or abridged that stage musicals compressed into two-hour films often have. Audrey is delightful as Eliza, essentially playing two completely different characters for the price of one, neither a clean match for her typical performances. Her acting in the transitional phase from foul-mouthed guttersnipe to elegant lady of high society is especially hilarious. A much better movie than I remembered or expected.
 
Rating: 4 out of 5
 
Audrey's Voice: Audrey Hepburn was a lady of many talents, but singing wasn't one of them, as you might have guessed after listening to her vocals in Funny Face and her husky, whispery performance of "Moon River" in Breakfast at Tiffany's. It's not even that she was a bad singer, just that she didn't have the vocal strength or range of a trained professional. Perhaps, then, she wasn't the best casting choice for the lead in a major Hollywood musical, but if they were willing to bank on her name, they should have let her do the singing. If there's a black eye on this movie, it's that they cast an actress with such a distinctive voice as Eliza Doolittle and then dubbed almost all of her sung lines with a vocalist who sounds nothing like her. Reportedly the studio had told her beforehand that she would be allowed to do her own singing for the part, so she was very upset when she found out that they'd dubbed her in secret. I don't blame her.
 
 
The Age Gap
Audrey Hepburn = 34
Rex Harrison = 55
 
Why that hat so big?

10. How to Steal a Million (1966)

This one feels of a species with Funny FaceLove in the Afternoon, and Paris When It Sizzles: lightweight romantic comedies that are pleasant enough to watch but ultimately kind of disposable. Of those, Funny Face stands the most apart by virtue of being a musical (even if it doesn't have any good songs), but I'd put How to Steal a Million above the others as the one I feel I'd soonest rewatch. A heist movie, there's a certain cleverness to its construction, even if the specifics of the scheme aren't completely plausible. Audrey doesn't get much to do in this movie, blindly trusting in charming leading man Peter O'Toole, Lawrence of Arabia himself, to make the plot happen around her, but she looks gorgeous and hits all her comedic marks dead center. Their romance isn't one for the ages but feels the most believable (and least creepy) out of those in her "lesser" movies. A fun, breezy flick to put on when you have nothing better to do.
 
Rating: 3.5 out of 5
 
Audrey's Look: Audrey does her best Suzanne Pleshette.
 
The Age Gap
Audrey Hepburn = 36
Peter O'Toole = 33 
 
 

8. Two for the Road (1967)

"We should have parted then."
 
"Why didn't we?"
 
"I didn't have the courage."
 
"You didn't have the courage? What courage did you need?"
 
"The courage to see that what was finished was finished."
 
A cousin to later dissolving-relationship dramas like The Way We Were and Blue Valentine, but unlike those movies, which tell a story about the beginning and end of a marriage, Two for the Road is more thematically a story about time: how it passes, how it repeats, how it changes and how it doesn't. It's the nonlinear forerunner to Richard Linklater's Before trilogy, a cinematic examination of a relationship's evolution throughout the span of a shared life.
 
It isn't necessarily Audrey's best performance, but it's certainly the most mature performance of her career. Having seen how she curated her image over her previous 14 films, even the one where she played a call girl, it was a shock to the system to suddenly see her openly talking about her sex life, having premarital sex and an extramarital affair, and getting called a bitch to her face, the latter of which was especially appalling. I wanted to punch Albert Finney on multiple occasions, not the least of which were the times I saw myself in him.
 
A very strong film, so maybe it's my own fault that I ultimately felt a little let down by it. It doesn't cut as deeply as a The Way We Were or a Blue Valentine, but it also doesn't offer the relief of an ending, even a sad one, even one you didn't want. Some things linger; some things go on; some things are never allowed to be finished, because we're too afraid of facing what comes after.
 
Rating: 4 out of 5
 
Audrey's Look: Still lovely but visibly in her late thirties, which made the scenes where she was playing an 18-year-old on a school trip a bit of an ask. Once she and Albert Finney separated from her distractingly younger peers, however, it was much easier to play the Hollywood game of make-believe.
 
The Age Gap
Audrey Hepburn = 37
Albert Finney = 30
 
"They don't look very happy."
"Why should they? They just got married."
 

2. Wait Until Dark (1967)

In the best performance of her career, her last before her nine-year retirement from Hollywood, Audrey plays a newly blind woman living in New York. Recently married to a photographer, she struggles with her reliance on her husband and a young neighbor girl while learning how to function after losing both her sight and her self-sufficiency. One day, the devil comes knocking on her door.
 
Stephen King called Wait Until Dark the scariest movie ever made. I wouldn't want to oversell it, because it's a bit of a slow burn and more inducive of anxiety and dread than visceral terror, but it is the only non-supernatural horror movie I can think of, apart from maybe Psycho, where that feeling of dread stuck with me after the movie, and returns each time I rewatch it. 

Audrey's helpless heroine, trapped in her own home and imperiled by a sinister conspiracy, calls to mind Barbara Stanwyck in Sorry, Wrong Number. Unlike that picture, however, where the atmosphere of doom grows more and more oppressive as the film goes on, Wait Until Dark lures you into a false sense of security with the theatrical, overly elaborate workings of the villains' scheme. When Alan Arkin bumbles his way into Audrey's apartment, rambling in a funny voice and wearing old-man makeup and a fake mustache, you might almost think the movie is veering into comedy. Until you get to the third act, when it becomes a nightmare.
 
Audrey made 16 films during the main period of her Hollywood career, and she's a pleasure to watch in each of them: a talented actress, yes, and immeasurably beautiful, but also possessed of some indefinable charm and grace, a magnetic screen presence that thrills the eye. She was a true Movie Star, but even in her strongest dramatic performances in The Nun's Story and Two for the Road, you're still aware that you're watching An Audrey Hepburn Movie. 
 
Wait Until Dark is, in my opinion, the first time she really disappears into a role. Actors always have a hard time pretending to be blind, especially when they can't rely on sunglasses to hide their eyes, but Audrey is completely believable in this movie. The way she moves, gestures, reasons, and interacts with the other characters makes you forget that she's actually sighted. The movie treats her blindness as neither a superpower nor a simple plot inconvenience; it’s something she has to reason her way around, forced to rely on her wits as the only weapon she has against "the greatest evocation of screen villainy ever."
 
Alan Arkin's performance as Harry Roat, Jr., from Scarsdale is one of the most chilling in movie history. Looking like a cross between Doctor Octopus and The Corinthian, he oozes across the screen like some kind of secretion. Every time he touches Audrey you want to throw up.
 
The movie is very thematically concerned with sight: Audrey's famously expressive eyes fill the screen, now dulled and sightless, while the sighted Roat masks his own with dark glasses. He wears and discards many masks throughout the film, both through the theatrical characters he plays and the way he allows himself to be perceived, as a comic-book villain hatching cartoon schemes. Although she's blind, or perhaps because she is, Audrey alone can see through his disguises, but "not all the way. Even now, not all the way." 

The final moments of the film, when the last of his masks fall away, become almost a precursor to John Carpenter's Halloween: "A dark house. A woman alone. A man with a knife." For my money, Wait Until Dark is the more terrifying of the two.
 
 
 
Rating: 5 out of 5
 
Audrey's Look: Absurd and unfair.
 
The Age Gap
Audrey Hepburn = 37
Efrem Zimbalist Jr. = 48 
 
 
After her Academy Award-nominated performance in Wait Until Dark, Audrey Hepburn retired from acting for close to a decade in order to spend more time with her children. Eventually she returned to Hollywood to make five additional movies, but I didn't watch those.
 

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