20 Movies To Watch In Your 20s

Twenty-Something Tuesday


1. Do the Right Thing

The premise is simple—racial conflict erupts during the hottest day of the summer—but you’ll be on your own to draw conclusions. Spike Lee’s powerful film asks difficult questions about race and gentrification, all in a stylish and energetic form.

2. 12 Angry Men

12 Angry Men is perhaps one of the most streamlined and understated films of all times. Shot almost entirely in a single room with twelve jurors as characters, the film evolves beautifully as the twelve men debate the accused’s fate. This is a truly character-driven film that’s remarkable for its ability to captivate with the barest minimum of elements.

3. American Beauty

If you grew up in the suburbs, you have got to see American Beauty, a film famous for presenting a wildly disturbing image of suburbia that rings all too true. From consumerism to lust, homophobia to first love, American Beauty is richly thought-provoking. Plus, you’ll never miss the “rose petal” allusion again.

4. Elizabethtown

Just when you’re on the cusp of “making it” is generally when your whole life crashes down around you and you find out what you’re really made of, what actually matters, and that the only truth in life is you have no idea what’s coming. For me, “Elizabethtown” is the Southern (and more relatable) “Garden State” with big noisy families, high expectations, a whole lot of crazy, and is about dealing with failure, change, death, and the freedom and truth found in a song and the open road.

5. Scott Pilgrim vs. the World

Feel like your life has no meaning while you’re in your 20s? Well, at least you’re not dating a high schooler. Scott Pilgrim is, and his life in a band that sucks seems pretty bleak until he meets the girl of his dreams (literally). Complications arise when he must defeat her seven evil exes. Michael Cera kills (and Kiernan Culkin steals the show) in this cleverly nerdy romantic/comedy/action movie based on a graphic novel.

6. Almost Famous

So you have no credentials but you’re trying to make a name for yourself in the working world. What 20-something can’t relate to that? Almost Famous follows William Miller, a teenager trying to make a name for himself as a rock journalist. William befriends the band Stillwater and their flock of “Band-Aids,” tagging along with the group on tour. He may be young, but William is smarter than most of the film’s adults. Almost Famous teaches you to take chances, break away from parental guidance, don’t forget about the little people when you make it big and most importantly, live in the now. “It’s all happening.”

7. Happy

This beautiful documentary takes you all around the world to figure out what makes people truly happy. It puts life in perspective and really gets you thinking about the things that matter and how to obtain the ever popular goal in life: Happiness. A must for people of all ages to watch.

8. Up

In my opinion, Up is arguably one of the best films ever made. It’s a heartening reminder that life is always an adventure. The first five minutes will break your heart, the rest of the movie will inspire you to hug your loved ones and book that trip you’ve been wanting to take.

9. Kicking and Screaming

This dialogue-driven 90s comedy explores the angsty, awkward, and often boring reality of life after college. From relationships to finding a job to changing dynamics between parents and children, this movie tackles the most confusing part of your 20s with some fantastically quotable one-liners.

10. Humpday

As you get closer to 30, you often find yourself settling into a life you may not have ever consciously chosen. In the Duplass Brother’s Humpday, we see two friends who went in opposite directions dealing with their own insecurity by challenging the other to come out of their comfort zone. One line in particular has long stayed with me: “You’re not as Kerouac as you think you are, and I’m not as white picket fence as you think I am.”

11. The “Cities of Love” Series

Despite a long break between the last film, New York, I Love You, and the two additions to be added this year, this series is essentially love letters to great cities around the world. The two films now available travel through Paris and New York, telling love stories in various neighborhoods to capture the true character of the location. Moving, funny, and often heartbreaking, Cities of Love is a must for the young romantic.

12. Away We Go

When Burt and Verona decide to uproot and find their dream home before the birth of their first child, they end up on a tour of cities they both have familial or long-time friend ties to across the US and into Canada. Their hunt for a place they can settle down and raise a family will resonate with those of us who have been used to moving from place to place during college.

13. Casablanca

Casablanca is a film everyone needs to see. Set during World War II at a Moroccan outpost of Casablanca, Casablanca is a bittersweet story about missed opportunities and difficult love. Humphrey Bogart and Ingrid Bergmen are immortalized in this film at the height of their careers. Although the film was released in 1942, it remains relevant today as the standard for romance and action.

14. The Shining

Quite possibly the scariest movie of all time, Stanley Kubrick directed Stephen King’s masterpiece novel of the same name. The Shining is also packed with lightbulb moments—similar to the experience of reading a Shakespeare play, you’ll come away knowing the origins of many oft-quoted lines like Jack Nicholson’s chilling cry of “Heeeere’s Johnny!” or the creepy dead twins that haunt scenes.

15. Amélie (or Le fabuleux destin d’Amélie Poulain)

Amélie will steal your heart as she fulfills her mission of restoring hope and love to the people around her, all while struggling to make her own unlikely love story come true. Filled with whimsical charm and just the right tinge of sadness, you’ll be so enthralled that you’ll hardly notice the subtitles. Amélie provides a new and surprising interpretation of the classic coming-of-age story.

16. Anastasia

This is a wonderful animated movie not made by Disney, so right from the bat it’s about nonconformity. “Anastasia” is about a twenty-something girl who is struggling to find herself and find a place in a cold (literally) world. She meets a boy named Dimitri, falls in love with said boy, slaps said boy, then graciously accepts him back after he was a total asshole (but can we all just agree that Dimitri is the hottest male animated character ever? OK.). She learns that trying to be someone you aren’t pretty much always turns out badly, and that it’s not OK for people to use you for their own gain, even if it seems enticing at the time. She learns about the importance of family and resilience and heart, and how to stand up against people who want to take your happiness from you (or, you know, your life, if your enemy is Rasputin). Also, Bartok the bat is super cute. Voices include John Cusack, Angela Lansbury and Meg Ryan, so you can’t pass that up, either.

17. Reality Bites

Watch Winona Ryder in all her alternative 90s girl glory as Lelaina Pierce, a recent college graduate attempting to make it in the entertainment world as a documentary filmmaker. Instead of instant success, she works an unfulfilling job as an intern for a morning talk show reminiscent of the Today show. Although some viewers may find the material a bit too 90s-centric, the film still captures the uncertainty and terror of life after college graduation. Janeane Garofalo plays Vickie, Lelaina’s wise-cracking, sex-positive best friend and nearly steals the show with her ruminations. Also, the famous scene in the Mobil mart is probably the highlight of the movie, besides a love-scorned Ethan Hawke serenading Lelaina with a Violent Femmes song.

18. A Beautiful Mind

Where to begin on why this movie is perfect for darlings in their 20s? I’m a bit biased because it’s my favorite movie EVER, but there are so many reasons to love it. For starters, John Nash (played by Russell Crowe) is just a young chap himself that enters Princeton University to develop a unique concept to change the world. He’s brilliant, determined, and completely socially incompetent. Alicia (played by Jennifer Connelly) ends up dating and marrying Nash, and she’s such a badass and never gives up on him even when he’s falling to pieces.

One of the primary reasons I love this movie is because of its raw and realistic depiction of mental illness (schizophrenia), and the subsequent overcoming of the complications is wreaked on the lives of the Nash family. When you’re feeling down on wherever your life might be going, this movie will remind you that against all odds, you’ll make it through it and be brilliant. It’s suspenseful and has so many damn feels that it makes me cry every time. It has something for everybody, and I highly recommend it.

19. Beaches

CC Bloom and Hillary Whitney are two young girls who meet at a resort in Atlantic City, and the movie follows their lifelong friendship. For most of their younger years they keep in touch via letters, and then Hillary quits her job as a lawyer to move out to live with performer CC in New York. The movie highlights many stages of not only their personal lives, but the strengthening of their friendship over the course of many years. Amazing example of how the best of friends don’t always have the perfect story.

20. God Grew Tired Of Us

The Lost Boys of Sudan are a group of refugees with an absolutely incredible story. This documentary shows both the life in the refugee camp in Kenya, and follows their journey after being invited to live in the United States. Watch them see an escalator for the first time, learn how to work a light switch, and scrape together a life with two jobs and night classes. This documentary makes you hyper-aware of the advantages that come with being born in the right place.

(Honorable Mentions: Crips and Bloods: Made In America, which Erin has already written about and Office Space, which sadly only becomes more pertinent as you progress through your career.)


What movies do you recommend? Comment below or tweet us @LitDarling!
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