Where do I begin with Ms. Audrey Hepburn? Class personified, and a role model to all women and an ideal woman to all men. A veteran of over 30 movies Audrey Hepburn is the quintessential classic Hollywood figure. In order to properly get a sense of who Audrey was, I’ll pick a few of her movies to get a complete understanding of why she’s so revered as not only a fashion icon but also as a tremendous actress.

Roman Holiday (1953)

Roman Holiday is one of my favorite movies.

If I’m ever introducing someone to classic films, this is the movie I make sure to put on the top of my list. I mean, how could someone be disappointed when they’re watching Audrey Hepburn and Gregory Peck frolic through Rome? Directed by William Wyler, Roman Holiday tells the story of Princess Ann and her struggles with feeling increasingly isolated in her royal life.

While on a scheduled trip to Rome, she decides to neglect her royal duties and escape the embassy that she’s staying at. The only problem is, her family gave her a sleeping pill to help ease her ‘anxieties.’ This causes her to sleepwalk throughout the city of Rome and eventually into the arms (and apartment) of journalist Joe Bradley, played by Gregory Peck.

When she wakes up the next morning, naturally, she’s utterly confused. Bradley quickly realizes who she is and wants to write a story on her. Ann, or Anya as she would later be called, rebuffs his advances and is hell-bent on exploring Rome by herself. Perturbed at her rejection, Bradley follows her around until they coincidentally meet up at a Roman cafe. For the rest of the film, we see Bradley shed his journalistic instincts while ultimately ending up falling in love with Anya as the two explore Rome together.

I will refrain from posting spoilers on this post because I want people who’ve never seen these films to enjoy the endings as they are. However, to those who have seen Roman Holiday, it’s one of the most touching and romantic movies in Hepburn’s filmography.

The fact that Hepburn won her first and only Academy Award is a testament to how wonderful and heartwarming this movie is. The chemistry between Hepburn and Peck adds to the movie’s already poignant nature, and the ending definitely capitalizes on that.

Funny Face (1957)

The next film on this list is a complete departure from the warm and fuzzy feelings of Roman Holiday. From the cobbled streets of Rome to the slick sophistication of Paris, Funny Face is a romantic-musical-comedy directed by Stanley Donen.

In the film, Hepburn plays a shy and rather homely bookkeeper named Jo Stockton who’s accidentally photographed by a fashion photographer during a photo shoot at her bookstore. Astonished at how beautiful this “random girl” was in the background of his photo, the man who photographed Jo invites her to model for him in Paris.

As they get to know each other better while snapping photos in front of iconic Parisienne landmarks, they eventually fall in love. Unfortunately, the pair face a plethora of obstacles that hinder them from actually consummating their relationship.

Also starring Fred Astaire and Kay Thompson, Funny Face is your archetypal classic Hollywood musical. With gorgeous scenic shots of Paris, a marvelous soundtrack and killer musical numbers (my favorite, in particular, is ‘Bonjour Paris‘) Funny Face rivals any MGM musical from that year; and the best part about that is, it stars Audrey Hepburn.

Breakfast at Tiffany’s (1960)

Fun Fact about this movie: Marilyn Monroe was Truman Capote‘s first choice to play Holly Golightly.

This ‘fun fact’ probably doesn’t come as too much of a surprise though. Being that the original version Capote intended to put on the screen was much more scandalous for 1960s audiences, the movie had to be toned down significantly in order to appease the censors. The tonal shift meant another, less sexual version of Holly Golightly had to be cast.

This is where Audrey Hepburn steps in.

Directed by Blake Edwards, Breakfast at Tiffany’s also stars George Peppard, Patricia Neal and Mickey Rooney in supporting roles. ‘BAT’ is a story about Holly Golightly’s relationship with writer Paul Varjak, played by Peppard, and the ups and downs that the couple goes through.

I have a special relationship with Breakfast at Tiffany‘s. It surely isn’t my favorite Hepburn film, but, I think it symbolizes a change in film roles that Hepburn would take from that point on in her career. You see, as the 1960s progressed, Hepburn’s filmography would increasingly feature a number of movies where the subject matter wasn’t as ‘lighthearted’ as her previous films.

Breakfast at Tiffany‘s was the first pillar, then rest came falling down in films like, The Children’s Hour, Two for The Road, Wait Unitil Dark and Charade. The movies I listed are a complete departure from the jovial and romantic movies of Hepburn’s earlier roles, and because of that is the reason why Breakfast at Tiffany‘s is a must see. Not only is the film an iconic piece of movie history, it also signifies a shift in Hepburn’s career.

How to Steal a Million (1966)

The last film on this list is apart of those later movies Hepburn would go on to do.

How to Steal a Million is a superb example of a 1960s era romantic-comedy. Directed by William Wyler and starring Peter O’Toole as burglar Simon Bonnet and Hepburn as Nicole Bonnet (the daughter of an art collector,) the movie follows Hepburn and O’Toole‘s character’s as they seek to steal back a piece of art that accidentally got loaned to a local museum.

Why are they stealing the art back? Well, it’s because Nicole’s father is an art forger, and if they allow his ‘art’ to be displayed for all to see, it most certainly wouldn’t bode well for his business.

What ensues is a massively funny and endearing rom-com that had me laughing and swooning (over Peter O’Toole) during its 2 hours and 7-minute runtime. I thoroughly enjoyed watching this movie and I hope all of reading this will have the privilege of watching it one day.

Conclusion

Audrey Hepburn is one of my favorite actresses. The fact that she had such a large imprint on movies in such a short amount of time is a testament to her charisma. I can only hope that you love the movies on this list as much as I do!