Think Audrey Hepburn and chances are we’re picturing the same thing: a sophisticated woman in black with a cigarette holder balanced in one hand and a croissant in the other, adorned with black opera gloves, an oversized necklace, and a crystal headpiece perched between a set of micro-bangs and a beehive updo. In fact, the image is hard to escape whether posted on the walls of teenage bedrooms, pinned to fashion Pinterest boards, or even recreated in Blair Waldorf’s dream sequence in Gossip Girl. While most of us recognize Audrey Hepburn as a Hollywood icon, not many have watched her movies, which shaped cinema and fashion in the 1950s and 60s.
I myself hadn’t seen any of her movies, excluding the time I started Breakfast at Tiffany’s on a plane in 5th grade before getting lost in the Transatlantic accents and falling asleep. However, in true Audrey fashion, I was reminded of that last attempt while at a Tiffany’s in downtown Portland. I was exchanging the broken chain of my favorite Return to Tiffany heart pendant, and noticed the picture of Hepburn in her iconic ensemble hung on the back wall.
On the drive home, I googled a Breakfast at Tiffany’s plot synopsis, which, to my surprise, was nothing like the sophisticated image I had in mind. The romantic comedy features Hepburn as a New York escort fleeing her annulled marriage, gold digging for eligible rich bachelors, purchasing clothes by dealing narcotics ring information, all while falling in love with her next door neighbor.
My plot investigation turned into a brief obsession that led me to watch nine Hepburn movies over winter break: Breakfast at Tiffany’s, Charade, How to Steal a Million, Wait Until Dark, Roman Holiday, Sabrina, Funny Face, Love in the Afternoon, and finally My Fair Lady. Below, I’ve listed my thoughts and ranking of each movie, as well as which are worth adding to your 2025 watchlist.
Roman Holiday (1953)
Roman Holiday is one of Hepburn’s earliest movies, and also my personal favorite. The movie has the charm of The Princess Diaries, following a runaway royal trying to pass as a normal girl and experience freedom, with a bittersweet La La Land ending.
I was expecting it to be difficult to adjust to the black and white film, but it gave the romantic elements a luminous quality and a vintage appeal to the shots of Rome. The movie also created my dream itinerary for a Roman vacation: traveling on vespas, eating at cafes, dancing on string-lit barges, and meeting a foreign stud with a shared journalism interest. The comical elements, cinematography, and romance make it a must-see for everyone.
How to Steal a Million (1966)
A true five star heist movie with a creative and amusing plot. Audrey Hepburn’s Nicole Bonnet seeks the help of an art thief to steal her father’s forgery of the Cellini Venus statue. The statue is in a museum and faces inspection. My favorite stunts include Hepburn and the male lead, Peter O’Toole, unlocking a museum closet from the inside and disabling the statue’s siren through a comical series of staged false alarms. The Paris backdrop and classic cars transport the viewer to the 1960s art world. Also, Hepburn’s Priscilla Presley eye makeup and Givenchy wardrobe are stunning to watch.
Sabrina (1954)
“It is late at night and someone across the way is playing ‘La Vie en Rose.’ It is the French way of saying, ‘I’m looking at the world with rose colored glasses.’” This line (also a trendingTikTok audio) sets the tone for the movie. As Sabrina, a chauffeur’s daughter for the lavish Larrabee family estate, travels to culinary school in Paris, she learns to find beauty in the world and how she carries herself through it, no longer pining for what she can’t have: David Larrabee.
I’d recommend the movie to anyone who watched Challengers, and craves a love triangle with an unexpected twist. The long island country club setting reminds me of The Great Gatsby (2013) and leaves you wanting to attend a Larrabee party.
Charade (1963)
This one is my favorite Hitchcock movie (despite not being directed by Alfred Hitchcock). Charade leaves the viewer in suspense until the end with numerous scenes of Audrey Hepburn running for her life in kitten heels and a wool trench coat. The movie is full of enjoyably outdated comedic bits like Carey Grant humming while taking a fully clothed shower, culprits dropping matches on spies in phone booths, falling through stage trap doors, and sharing threats while handlessly passing an orange as part of a bar entertainment segment.
Wait Until Dark (1967)
Wait Until Dark stands out as one of Hepburn’s latest films, and as the only thriller in the ranking. Once you get through the slow start (my dad fell asleep after 30 minutes), the film builds into an intensely woven plot. If horror isn’t your genre, rest assured, you can find comfort in the fact that the plot is so elaborate and far-fetched, you’d never find yourself in a similar predicament. The film follows Susy, a blind woman, who unknowingly comes into possession of a doll filled with heroin. This lures criminals seeking the contraband into her home. Audrey Hepburn’s portrayal of Susy’s vulnerability and fearful realization of their invasion is genuinely unnerving and her screams ring of pure desperation. Susy ultimately outsmarts her perpetrators, setting up traps reminiscent of Home Alone, to outmaneuver them until the police arrive.
Breakfast at Tiffany’s (1961)
It’s impossible to discuss Breakfast at Tiffany’s without first addressing the overt racism in the film. Hepburn’s landlord, Yunioshi, played by a white actor in yellowface, portrays an offensive caricature of Japanese Americans.
However, despite its flaws, Breakfast at Tiffany’s has stood against time as her most iconic role, largely due to its showcase of 1960s fashion and its exploration of self discovery. By the end of the film, Golightly realizes she’s caging herself by detaching from loved ones in pursuit of superficial happiness. The final rain kiss between Hepburn, her neighbor, and her cat is both humorous and heartfelt. As someone who’s also perpetually locked out of their half-furnished apartment and spends too much of their money on clothes, I found the character of Holly Golightly to be the most relatable.
Love in the Afternoon (1957)
Love in the Afternoon is yet another movie where Hepburn’s character finds herself in an imaginatively unique circumstance and a romance with a man in his 60s. I’d recommend the movie to any fan of Lana Del Rey as the movie romanticizes the connection between Hepburn and emotionally detached Gary Cooper, who’s old enough to be her grandfather.
After finding Cooper in her private investigator father’s files, Hepburn makes frequent visits to his hotel at the Paris Ritz while he ironically hires her own father to figure out her identity. The movie has the slowest plot out of the nine and is essentially 2 hours of Hepburn making older Cooper jealous. That said, if you idealize picnic dates in Paris, expensive fur coats, and rich men, it could be worth the watch.
My Fair Lady (1964)
This movie ranks low as it’s an almost 3-hour musical with no memorable songs. In the movie, Hepburn seeks the help of a linguist to fix her lower-class Cockney accent, and hopefully enter the workforce in higher society. Hepburn’s dramatized Cockney accent is drilling, which left me frequently turning down the volume, but there were many comedic moments that drew me back in; specifically Hepburn telling a group of high society Englishmen how her mother couldn’t have died of sickness, and instead must of been “done in” as she had the strength to bite the bowl off the spoon as her father ladled gin down her throat. The culmination of Hepburn’s transformation takes place at the queen’s ball, where Hepburn passes for a princess in a stunning jeweled gown (later recreated by Kendall Jenner at the Met Gala).
Funny Face (1957)
I have to note my own biases here since my other bottom ranking is also a musical featuring a transformative makeover. Since the dance numbers and gorgeous Givenchy collection were the only things that captivated me, I’d have had the same appreciation had I watched the film in silence.
The viewer must suspend their disbelief and see Audrey Hepburn as a dull and forgetful book clerk before her makeover into the muse of a fashion line launching in Paris. Hepburn’s character subscribes to Empathicalism: a cult-like group devoted to the philosophy of empathy (profound, right?) before the leading philosopher comes on to her at a convention in Paris. It’s in this scene that she abandons her lifelong ideology and makes it to the fashion show just in time.