Top 35 Movies to Watch in Your 20s

Top 35 Movies for Twentysomethings | AllGroanUp.com

What are the most important movies to watch in your 20s?

Movies about finding yourself. Movies when you have a crush. Or just movies for young adults for inspiration, insight, or all-too-needed hilarity into this crazy twentysomething life.

When you’re looking for movies to watch, where do you go to find a good film?

I posed this question on the All Groan Up Facebook page, through my Twitter account, and I peered deeply through my long list of influential movies that helped define and refine my 20s.

The list grew and grew, and below are the top 35 movies to watch in your 20s (not necessarily in order), with some shout-outs to those who recommended them. I also added life-lessons taught through these movies.

From big block-busters to little known documentaries, this list contains all the movies to watch in your 20s.

(If you’re looking for something to read as well, check out my 27 books to read in your 20s that influenced me while I wrote my new book 101 Questions You Need to Ask in Your Twenties and my best-selling book 101 Secrets For Your Twenties.)

For your viewing pleasure, for the next blizzard, “well-being sick-day”, or just your next bottle of wine, All Groan Up presents the top 35 movies you need to watch in your 20s…

Top 35 Movies to Watch in Your 20s | AllGroanUp.com

Top 35 Movies to Watch in Your 20s 

35. Office Space (1999)

Let’s get this list off to a running start with a cult-classic that taught an entire generation one simple truth: Death by cubicle is a terrible way to die.  

Mix mundane cubicle life, gangster rap, flare, a prized stapler and fantasies to smash the company’s printer with a baseball bat, and you have what Raylan on Facebook said “should be considered a documentary.” (Watch Office Space)

34. The Graduate (1967)

The quintessential angsty, funky and “floating” 60s classic that teaches some unhealthy ways to escape the post-college angst.

And that you need to find an old Paul Simon album right now (who I once showed how to use a bench-press, but that’s a story for a different article).

Memorable Quote: It’s like I was playing some kind of game, but the rules don’t make any sense to me. They’re being made up by all the wrong people. I mean no one makes them up. They seem to make themselves up. (Check out The Graduate)

33. The Words (2012)

I was recently introduced to this gem of a movie by my sister-in-law Kendra, and instantly fell in love. It has great actors (Bradley Cooper, Jeremy Irons, Dennis Quaid, Zoe Saldana, etc), a really thoughtful, intriguing script, and I felt the movie encapsulated perfectly the struggling, dreaming twentysomething who is fighting with everything to truly be someone. And of course the story thread of a young writer getting rejected by every publisher rang all too true to  my own story. Please watch and I’d love to hear what you think.

Life Lesson: As you fight, cry, and claw up the steep path towards your dream in your 20s, taking the shortcut might be the worst path you could take. (The Words on Amazon)

32. Groundhog Day (1993)

That’s right, woodchuck-chuckers – it’s…GROUNDHOG DAY!

This is my favorite Bill Murray movie. There I said it and I’m not taking it back. If you haven’t seen Groundhog Day (and who hasn’t) – bored, cynical, disgruntled weatherman Phil Connors gets stuck re-living the same non-eventful day, in the non-eventful town. (Sounds kind of like twentysomething life, doesn’t it).

Life Lesson: Sometimes the only way to get out of the same old rut is to find the meaning within it. (Watch Groundhog Day)

31. In A World (2013)

Lake Bell who writes, directs, and stars in this quirky, indie comedic gem about a struggling movie voice-over artist, has a lot to say about fighting for a dream, the people who will (and won’t) help you along the way, and what it can look like to be a woman trying to break into a male dominated industry. (Watch In a World for free with Amazon Prime)

30. Garden State (2004)

I feel like I have to include this one even if I personally feel like it’s overrated. Yelling down into “the large gaping hole” metaphor was my breaking point. Feel free to advocate for it in the comments below. Or don’t. (Watch Garden State)

29. It’s a Wonderful Life (1946)

It’s hard to imagine now that It’s a Wonderful Life was a major flop when initially released. It only starting becoming the iconic classic that is today 30 years later because a clerical error placed it in public domain, making it a television mainstay.

Try to watch It’s a Wonderful Life with new light and see the important messages about what it means to be a success, have an impact, and live a meaningful life within the mundane.

When George Bailey has his breakdown in his living room, smashing all the dreams he held on to as his life seemingly falls apart, I still get chills. (Watch It’s a Wonderful Life)

28. Devil Wears Prada (2006)

It’s Hollywood. It’s slightly cliche. But in the end, poses a good question about what sacrifices will you be willing to make to get to the top. (Watch The Devil Wears Prada)

27. Danielson: A Family Movie (or, Make a Joyful Noise Here) (2006)

A little known indie documentary about Daniel Smith and his traveling Christian family band who wear nurses outfits while playing in dive bars to bring the healing of Christ into the room. I think this movie shows one of the more heartfelt stories of what it means to create, have faith, and enjoy the people around you while you do. And if you’re a fan of music savant Sufjan Stevens (as I am) you’ll especially enjoy this documentary. (Snag Danielson: A Family Movie)

26. 500 Days of Summer (2009)

Love, love, love this movie. I think it’s one of the best scripts in the romantic comedy genre that’s come around in the last fifty years. I’m serious. I don’t think I’ve seen a movie that better encapsulates the ambiguities, complexities, pains, and misunderstandings of relationships. And the split screen scene of “Expectations” vs “Reality” should be required viewing for all college graduates.

Just remember — this is not a love story. (Watch 500 Days of Summer)

25. The Shawshank Redemption (1994)

Probably every list should include this movie, so I’ll go ahead and do my part.

Memorable Quote: “Get busy living or get busy dying.” (Watch Shawshank Redeption)

24. Away We Go (2009)

It might not make you want to have kids for a while, but this comedy staring John Krasinski and Maya Rudolph does offer some insights into one of life’s biggest transitions — becoming parents. (Watch Away We Go)

23. and 22. Dead Poets Society (1989) and Good Will Hunting (1997)

Two iconic roles by Robin Williams and the launching of Matt Damon and Ben Affleck. Both of these movies, as my friend Ryan aptly described, are about “carpe diem with your gifts.”

Life Lessons: Don’t run from who you are. Let go of the fears, insecurities, and pains from the past. Embrace who are, with all you are. (Watch Dead Poets Society and Good Will Hunting)

21. The Big Chill (1983)

I’ve never watched it! Yet it got enough votes that I had to go with the blind include. Hope to check it out myself soon. (Watch The Big Chill)

20. Midnight in Paris (2011)

A good, if not an entirely amazing, Woody Allen movie that I think is worth putting on here for one key lesson: Nostalgia is a liar. (Watch Midnight in Paris)

19. 50/50

It has Seth Rogen in it, so you know ample amounts of cringe worthy crudeness is there as well. But for a heart-felt, painful, funny movie about a twentysomething dealing with cancer, Joseph Gorden Levitt nails it as he usually does. (Watch 50/50)

18. Ordinary People (1980)

Winner of The Best Picture, it’s extremely well done and a tough one to watch at times because it portrays the pain of loss, depression, and a struggle to find peace all too accurately. It’s kind of a mix of Good Will Hunting and Donnie Darko. Watch this movie with a friend so you have someone to discuss the movie with after. (Watch Ordinary People)

17. Up (2009)

Of course an animated movie about an elderly man flying across the world in his house carried by balloons is included in a list for top movies to watch in your 20s. Just makes sense, right? But just the first ten minutes of the movie alone gives anyone enough to think about.

Life Lesson: Sometimes we need to watch the end of someone else’s story to bring back meaning for our beginning. (Watch Up)

16. When Harry Met Sally (1989)

Can men and women truly be just friends? A Billy Crystal, Meg Ryan classic that navigates the complexities of relationships, change, and what it means to love. (Watch When Harry Met Sally)

15. Stories We Tell (2012)

A surprising, intriguing, intimate look at one family and the way the untold and re-told stories from the past are still affecting everyone’s present. Some really good writing and a really interesting case-study of sorts into elements of message and memory, and it all changing depending on who’s telling it. The ideas of what’s “real” and what’s fabricated, in film and in life. And as well a multi-layered look at family, consequences, etc. I found it really intriguing and I think for anyone grappling with family complexities and events from the past, could really benefit. Plus it’s streaming free on Amazon! (Watch Stories We Tell)

14. Band of Brothers (2001)

I’m cheating a little with this one as its an HBO mini-series, but it’s worth bending a few rules to include. Sometimes when life feels like an epic battle, it’s good to watch an amazing story of a group of men going through a real one for some life perspective. Loyalty. Pain. Sacrifice. Victory. Loss. It’s all there. One of the best. (Snag Band of Brothers)

13. Fight Club (1999)

Not for the faint of heart, it’s as sick as it is genius. Yet many of the critiques and commentaries about living our collective IKEA, Starbucks lifestyles isolated from one another are pretty powerful.

Memorable Quotes: “We’re the middle children of history, man. No purpose or place. We have no Great War. No Great Depression. Our Great War’s a spiritual war… our Great Depression is our lives. We’ve all been raised on television to believe that one day we’d all be millionaires, and movie gods, and rock stars. But we won’t. And we’re slowly learning that fact. And we’re very, very pissed off.” (Watch Fight Club)

12. Reality Bites (1994)

My friend Erin described Reality Bites as  “perfect for every college grad who still has no idea what to do with their lives.” I had quite a few votes for Reality Bites and is one of the few on this list that I still need to see. (Watch Reality Bites)

11. Amazing Grace (2006)

Powerful movie about William Wilberforce and his fight for abolishing the English slave trade. As my friend Marcus acutely described about the importance of Amazing Grace, “Young people need to see that it can take years of painstaking, hard, methodical, sometimes depressing work to create that sought after lifetime achievement.” (Watch Amazing Grace)

10. Walk the Line (2005)

Joaquin Phoenix and Reese Witherspoon playing Johnny Cash and June Carter might be my favorite musical duo ever. The music! The acting! Plus a powerful story with many important messages about the dangers of medicating, the power of faith, and the yearning to create. One of my all-time favorite movies.

Life Lesson: You can achieve all your dreams, but it won’t mean much if you’re medicating from the pains of your past. (Watch Walk the Line)

9. Enron: The Smartest Guys in the Room (2005)

A must-watch documentary for our generation so we can avoid some of the mistakes from the past. And a good reminder that sometimes the smartest guys are the biggest idiots. (Watch Enron)

8. The Secret Life of Walter Mitty (2013)

Probably one of the biggest surprises I received from a movie in a while. I thought Ben Stiller, the director and actor, absolutely killed this one. Love the soundtrack, especially the songs from Jose Gonzalez, and the cinematography was beautiful. And the message of living life like you mean with audacity and adventure. Loved it. (Watch The Secret Life of Walter Mitty)

7. Buck (2011)

A sauntering documentary about real-life horse whisperer Buck Brannaman surprisingly has a lot to teach all of us about dealing with pain, anger, and finding peace within yourself. Granted I’m a sucker for horse movies and beautiful landscapes, but this intimate documentary is powerful. And you can stream it free right now on Amazon. (Watch Buck)

6. Swingers (1996)

Any movie where Vince Vaughn is on a table, screaming “You’re all growns up now!” has to be included on the list. This cult classic is up there with Office Space in my opinion and even to this day says a lot about trying (and failing) to live the LA dream. (Watch Swingers)

5. Lord of the Rings (2001 – 2003)

I read this series three times growing up, so I’m still partial to the books, but there are too many powerful lessons in these movies to not include. My favorite relationship is between Sam and Frodo and the great reminder about the power of friendship, even when it feels like you’re on our journey alone. (Snag Lord of the Rings)

4. Searching For Sugar Man (2012)

Let’s be honest, pretty sure I cried twice during this amazing documentary. For anyone struggling to create, do more, be heard, and find your place, you have to watch this documentary of musician Sixto Rodriguez. This one spoke straight into my soul and hasn’t gone away.

Life Lesson: Even if your impact feels minimal right now, you have no idea how far the ripples will go. (Watch Searching For Sugar Man)

3. Warrior (2011)

(Disclaimer: I have a deep movie-crush on Warrior. And again I cried at the end. Like a little boy who lost his favorite stuffed animal out the car window)

This is the best under the radar movies ever. Honestly. It should’ve exploded the radar on it’s way through the orbit, but I think because of some failed marketing it didn’t have time to take off in theaters.  Joel Edgerton, Tom Harding, and Nick Nolte are amazing. The ending, one of my all-time favorites.

Yes the story is told through mixed martial arts fighting, but please don’t let that stop you from watching an incredibly impactful film about family, redemption, and forgiveness.  (Please go and watch Warrior)

2. Silver Linings Playbook (2012)

Bradley Cooper, Jennifer Lawrence, Robert De Niro, and Jacki Weaver are all amazing. The comedic and painful look into dealing with mental illness is definitely a powerful one. (Watch Silver Linings Playbook)

1. Into the Wild (Watch Into the Wild)

Into the Wild is based on the book and true story of Christopher McCandless who gives away all his money after college to go on a great Alaskan adventure. It made my top books for twentysomethings as well, even though this might be one of the few times that I liked the movie better than the book. I think this is one of the most powerful warnings for our generation struggling to find answers and doing so mostly by ourselves. Don’t struggle through your quarter life crisis alone. As I wrote about Into the Wild in my book 101 Secrets For Your Twenties:

Don’t allow loneliness to become isolation.

Don’t pull your head inside your shell thinking only you can protect yourself. Don’t go on a dangerous Great Alaskan Adventure to live off the land all by yourself. That’s not a search for life, that’s suicide.

We need to know, and to be known.

Invite a friend or two over for dinner. Talk, laugh once or twice— even if it’s forced, and before the meal is over you might just notice your friends are chewing on the same questions you are. And at that moment of honest conversation, you will see light in the dark and dusty corners.”

There it is the top movies for twentysomethings! What movies did I foolishly miss? What movies did you love? I’d love to hear from you in the comments on this article.


101 Questions You Need to Ask in Your Twenties---small-cover-imageIf you’re looking for some more inspiration and insight for your 20s, then check out my newest book 101 Questions You Need to Ask in Your Twenties.

Written in the same easy-to-read style and humor as my best-selling book 101 Secrets For Your Twenties, but this time we’re digging even deeper.

See what readers are saying about 101 Questions You Need to Ask in Your Twenties

13 Comments

  1. Amber D

    Great List!!! Can’t wait to watch some of these! Facebook and tweet-worthy.:) Thank you for putting time and thought into this.

    Reply
  2. Sean

    Since 35 seems like a random number, (I was think 20something would have been better), I’d like to add “Ferris Buehler’s Day Off”. “Life moves pretty fast, if you don’t stop and look around for a while you might miss it!”.

    Reply
  3. Susan

    The Giant Mechanical Man with Jenna Fischer. I can’t name a movie in the last 5 years that has resonated so much with me. Or had a character that I could relate to so much. I think its great for people who are not really sure where they’re headed. Especially if everyone around you is frustrated that you can’t just fall in line with the rest of the world.

    Reply
  4. Carol

    I loved that Warrior is in the list, I love the movie and I keep re-watching it. It was so real to me, I cried, I felt all the emotions, the pain…I could go on all day. You said it best, it’s about family and forgiveness.

    Reply
  5. Paul Angone - All Groan Up

    Thanks Bola! You’re great at writing concise nuggets of wisdom as well. Excited for you to watch some more of these great movies..

    Reply
  6. Nys

    I adore your blog and this isn’t relevant to the article but your blog isn’t Facebook mobile app compatible! Not sure if you can fix it but thought you’d like to know. It’s not easy to read due to the menu bar. I’ve included photos.

    Reply
  7. Joe

    “Hector and the Search for Happiness” (essentially Walter Mitty but much, much better IMO) and “Sleepwalk with Me” – check em out

    Reply
  8. Joe

    Also, “Spread” starring Ashton Kutcher – movie about a young stud looking to make it as an actor, falls in love and realizes his ivory tower is just naivete.

    Reply
  9. Fernando H

    Dude! You still havent watched Ikiru!!

    Reply
  10. Jen

    I love to see Into the Wild on lists like these, it’s absolutely a movie that everyone (regardless of age) should see. A truly heartbreaking but inspiring story, makes me want to move to Alaska too 🙂

    Reply

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