Culturally Important Movies Every 20-something Woman Should See

I love movies. I love costumes, sets, writers, lighting and videography. When I ask my friends, “did you notice that this movie was shot in Technicolor, despite it being an outdated film type at the time?” they frequently respond, “no, why would I and why do you know that?” I am a true lover of movies; therefore, I have seen an awful lot of them.

Good movies are in no short supply, I would find it difficult to narrow down the greatest movies I have ever seen to compile a list of the 100 best movies of all time. However, when I place the limit of ‘best movies with a well written female lead’, I struggled to find fourteen movies to place on a list. When poling friends as to which female led movies are their favourites, I would get an initial list of flimsy chick-flicks, after applying the limiting factor, I was lucky to get one response from them. This current list of culturally important movies every 20-something woman should see is the result of several months of research and as you will see, it does not contain a single chick-flick, bad actress (in a leading role) or weak female character.

Marie Antoinette (2006)  IMDb

Female Lead:

Kirsten Dunst

Why it is Important:

Whether they are remembered in a positive or negative light, I have always seen the importance of knowing the stories of past influential women. Sofia Coppola writes an interesting Marie Antoinette, played perfectly by Kirsten Dunst. For the first time, the character of Marie Antoinette is written more as a real woman and less like the caricature that the real last Queen of France became. With Coppola’s writing and direction, we see a side of the story of Marie Antoinette that is frequently overlooked, the Queen’s motivations and tragic decline that led to her beheadal at the climax of the French Revolution. This movie brings Versailles back to life and back to a time when the paint on the portraits was fresh and the desserts were decadent. Kirsten Dunst holds her own among the beautiful sets and costumes that are so over-the-top, they remind you why the starving French revolted.


Cry-Baby (1990)  IMDb

Female Leads:

Amy Locane and Ricki Lake

Why it is Important:

This movie has been my favourite since I was 3 years old. When I was a child, I loved it for the costumes, now that I am old enough to understand, I love it for the unique plot… and the costumes. This movie has shaped my life. I see it as no coincidence that this movie takes place in 1954 and I base my entire style and character on 1950s vintage fashion and etiquette. Growing up, I always saw myself as Allison Vernon-Williams, “scrape: part square, part drape”, a rebel in the guise of a straight-A student. What makes this movie perfect is its inclusion of classic 1950s-era actors such as, Polly Bergen, Troy Donahue and David Nelson.


An Education (2009)  IMDb

Female Lead:

Carey Mulligan

Why it is Important:

This intriguing story about a young 1960s-era London suburb school-girl who must choose between a promising education at Oxford University and an exciting life as the young wife to a charismatic older man touches every young woman whom has ever debated the costs and benefits of education versus procreation. This movie is beautifully done with striking sets and costumes, traditional British wit and a young actress strong enough to stand out among a more experienced cast. The character of Jenny, played by Mulligan, is well written and well preformed. Her character is strong, intelligent and flawed, three attributes rarely seen in female roles today.


Revolutionary Road (2008)  IMDb

Female Lead:

Kate Winslet

Why it is Important:

This movie is a strong contender for my new favourite movie. This movie is beautifully disconcerting. Adapted from Richard Yates’ Revolutionary Road, published in 1961, the movie follows a young housewife in the 1950s American suburbs who struggles to come to terms with the realization that this is all her life will ever be. It makes a young woman consider her own life, goals and choices. Kate Winslet does some of her best work on this film, inducing several goose-bump moments. I have never before seen a movie that depicted such realistic conversations between a married couple. Though it is placed in a different time, this story is timeless. It you choose only one movie on this list to seek out and watch, make it this one.


(500) Days of Summer (2009)  IMDb

Female Lead:

Zooey Deschanel

Why it is Important:

Although some people, like my friend Sarah, point out that Zooey Deschanel tends to play the same character in every movie, she does play that adorably independent character well. This movie is wonderfully styled; the costumes and music alone will make you fall in love with it. This movie states in the first few minutes that it is not a love story, and although it is centered on a relationship, it sets out to prove this statement through an interesting, non-linear timeline. Although Deschanel’s character, Summer, is a bit of a stereotypical, Annie Hall-esque, unattainable, lofty dream-woman, she manages to play her with dignity and character. This may not be the best movie on my list, but it is certainly the most entertaining.


Breakfast at Tiffany’s (1961)  IMDb

Female Lead:

Audrey Hepburn

Why it is important:

This is my favourite Audrey Hepburn movie. She plays the perfectly flawed prostitute, Holly Golightly of 1960s New York City. This movie changed style and fashion standards for the next 40 years; who doesn’t know the iconic image of Audrey with her telescoping cigarette holder. I challenge you not to cry when Holly jumps out of the cab in the pouring rain, runs up to Paul and tearfully questions, “where’s the cat?”


Eternal Sunshine of the Spotless Mind (2004)  IMDb

Female Lead:

Kate Wislet

Why it is Important:

This movie has one of the most interesting plots and concepts that I’m seen in a long time. I love that it takes place in the winter, so few movies are set in the dead of winter that only one other comes immediately to mind, Fargo. Winslet plays the eccentric and far-from-perfect girlfriend of a serious Jim Carry. Like many women today, she thinks she needs to find a man that will accept her for her personality flaws, instead of working on them. Kirsten Dunst is also quite charming in this movie.


Amélie (Le fabuleux destin d’Amélie Poulain) (2001)  IMDb

Female Lead:

Audrey Tautou

Why it is Important:

This movie is so visually stunning that it is hard to keep your eyes on the subtitles. Tautou plays the cute, quirky and naïve Amélie, a young woman exploring her personal world as it intertwines with the lives of strangers in the streets of Paris. Simply watching this movie somehow adds a whimsical appeal to the rest of your life.


Fur: An Imaginary Portrait of Diane Arbus (2006)  IMDb

Female Lead:

Nicole Kidman

Why it is Important:

I love this movie for its oddness. Based on a true character, played by Kidman, Diane begins as a placid, unfulfilled assistant to her photographer husband in 1958 New York City. She is a timid woman who has never been able to explore her more deviant interests. After cautiously befriending an eccentric neighbour, Diane is able to escape her constrictive former life and become a talented and respected photographer. This movie shows us that beauty and love can exist in the most unusual and unexpected places.


Reality Bites (1994)  IMDb

Female Leads:

Winona Ryder and Janeane Garofalo

Why it is Important:

This movie epitomizes the 1990s, yet remains relevant as it depicts a stage of life that almost all of us go through. All of our lives, people are telling us what comes next, high school, college, then job, the first stages are easy but most of us seem to get lost between college and job. This movie follows an ambitious valedictorian who struggles to find a good job, find love, maintain her college friendships and learn how life works in the real world. It also explores bold issues for the time such as sexuality and AIDS.


Some Like it Hot (1959)  IMDb

Female Lead:

Marilyn Monroe

Why it is Important:

This movie remains culturally important because it shows us why a generation fell in love with Marilyn. She plays the sweet and troubled, Sugar Kane Kowalczyk, in a way that no one else could. There is just something special about Marilyn.


Romeo + Juliet (1996)  IMDb

Female Lead:

Claire Danes

Why it is Important:

Who doesn’t love Shakespeare? We continue to study his works today because the tragic and timeless plots remain relevant today. This movie blends the original lines of Shakespeare with the now-nostalgic aesthetic of the 1990s beautifully. It’s not hard to fain charisma and attraction with a young Leonardo DiCaprio, but Danes does it so superbly that people found it hard to believe they were not in a real-life relationship. Despite working with a female character that is certainly not Shakespeare’s best work, Danes gives Juliet substance. She does not let Juliet become the weak, mindless follower who kills herself for a boy she met three days ago that lesser actresses have allowed.


Gone with the Wind (1939)  IMDb

Female Lead:

Vivien Leigh

Why it is Important:

Leigh’s Scarlett O’Hara is one of my favourite female characters in film. She is strong, beautiful, cunningly intelligent and stubborn. She always puts her happiness first and insists on being the centre of attention. She could have gone on to have quite an enjoyable life of being admired and adored without correcting these flaws if the civil war had not broken out in her idyllic world. The costumes in this movie are astounding, I have never in my life seen a dress as amazing as Scarlett’s in the opening scenes of this movie.


Girl, Interrupted (1999)  IMDb

Female Leads:

Winona Ryder, Angelina Jolie and Whoopi Goldberg

Why it is Important:

Based on a true account of a woman’s stay in a mental institution in the 1960s, this movie sheds a realistic light on both society’s treatment of women and mental health treatment at that cataclysmic period of time. It explores taboo subjects such as mental illness, suicide, sexuality and race. This movie is full of strong, well-written female characters and rivals One Flew over the Cuckoo’s Nest for best mental institution movie.