film 20 Movies to Watch in Your 20s

Ann Casano
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Turning 30 means you’re getting old. It sounds harsh, maybe even a bit cynical. However, the fact of the matter is you’re not in your 20s anymore. You’re suddenly expected to act like an adult, work a good job, maybe even already have a family. But here’s the thing, being in your 20s is not all wine and roses. It’s confusing and there is no longer a road map on how to live life. One great thing about movies and films is that they offer audiences guidance, through entertainment. Here are 20 movies to watch in your 20s, that might help you figure things out, if just a little bit.

These are must-see movies for twenty-somethings. Some of the films on this list are neat and tidy life lessons. Others are stern warnings on what not to do. Then there are those that just remind you how important your friends are in life.

Most of these films are inspiring in some way. Perhaps the most significant films on this list revolve around relationships. Many hope to find “the one” when they’re in their 20s. You give your hearts and souls to significant others, but part of the process of finding that special someone often involves getting dumped or breaking a heart.

Turning 30 is a milestone; don’t let anyone tell you it’s just a number, or that it's not a big deal. It is a big deal! One surefire way to help the process of getting old is to check out these movies to see before you turn 30. Don’t say no one warned you!

Reality Bites is listed (or ranked) 1 on the list 20 Movies to Watch in Your 20s
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Reality Bites is a Generation X staple that oozes 1990s ideology. However, the message is universal and translates to every generation. College graduates will not automatically get their dream job, and the sudden realization that the real world and adult love is truly a struggle, will be a certain slap in the face.

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Actors: Winona Ryder, Renée Zellweger, Ben Stiller, Andy Dick Ethan Hawke, + more

Initial Release: 1994

Directed by: Ben Stiller

Genres (Film): Romance Film, Drama, Comedy

Tagline: A comedy about love in the '90s.

Rated: PG-13 (USA)

Also Ranked

#77 on The Best Movies of 1994

#96 on Movies with the Best Soundtracks

#60 on The Greatest Date Movies of All Time

#71 on The Best Films Directed by Famous Actors

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Fight Club is listed (or ranked) 2 on the list 20 Movies to Watch in Your 20s
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Although Fight Club can be a confusing film with a twist ending that will knock your socks off, the movie's message remains perfectly clear. The things you own end up owning you. Do you really need that new wooden bench from IKEA? Is buying that spice rack going to make your life any better?

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Actors: Brad Pitt, Jared Leto, Helena Bonham Carter, Edward Norton Meat Loaf, + more

Initial Release: 1999

Directed by: David Fincher

Genres (Film): Film adaptation, Cult film, Drama

Tagline: Creates a thick rich lather. Like rabies., Hand soap? How about swollen and broken fist soap?, Mischief. Mayhem. Soap., The best fat for making soap comes from humans. Wash your feminine side clean off., + more

Rated: R (USA)

Also Ranked

#39 on The Very Best Oscar-Winning Movies

#5 on The Best Psychological Thrillers of All Time

#28 on The Most Rewatchable Movies

#77 on The Greatest Action Movies of All Time

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Do the Right Thing is listed (or ranked) 3 on the list 20 Movies to Watch in Your 20s
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Race is today, and will always be, an issue. No filmmaker explores racial tension better than Spike Lee. Do the Right Thing examines a single day in a racially divided city on the hottest day of the year. Audiences walk away from the film with all the right questions to ponder, but Lee is not arrogant enough to provide any clear answers - that's up to the audience.

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Actors: Samuel L. Jackson, Martin Lawrence, Spike Lee, John Turturro Rosie Perez, + more

Initial Release: 1989

Directed by: Spike Lee

Genres (Film): Indie film, Drama, Comedy, Ensemble Film

Tagline: It's the hottest day of the summer. You can do nothing, you can do something, or you can...

Rated: R (USA)

Also Ranked

#29 on The Best Movies Directed by the Star

#8 on List of Black Movies, Ranked Best to Worst

#28 on The Best Hood Movies

#95 on The Best Hipster Movies

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Eternal Sunshine of the Spotle... is listed (or ranked) 4 on the list 20 Movies to Watch in Your 20s
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Have you ever been in a failed relationship that hurt you so much you wish you could erase the entire memory of the experience? Is it better to have loved and lost than to have never loved at all? Charlie Kaufman's screenplay teaches viewers that pain is okay; it's a part of life and love really, really hurts. But in the end, when the wounds heal, we will risk everything to experience it all again, warts and all.

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Actors: Kate Winslet, Kirsten Dunst, Jim Carrey, Mark Ruffalo Elijah Wood, + more

Initial Release: 2004

Directed by: Michel Gondry

Genres (Film): Romance Film, Science Fiction, Drama

Rated: R (USA)

Also Ranked

#113 on The Greatest Sci-Fi Movies of All Time

#50 on The Best Psychological Thrillers of All Time

#92 on The Best Movies Roger Ebert Gave Four Stars

#29 on The Best Oscar-Winning Screenplays

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Frances Ha is listed (or ranked) 5 on the list 20 Movies to Watch in Your 20s
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Okay, first off, let's get this out of the way: it's perfectly acceptable to film a present day comedy in black and white. Frances Ha is another kick you in the face movie. Life is a struggle after college - you need to get over it, or you will never succeed.

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Actors: Greta Gerwig, Adam Driver, Michael Zegen, Charlotte d'Amboise Juliet Rylance, + more

Initial Release: 2012

Directed by: Noah Baumbach

Genres (Film): Drama, Comedy

Rated: R (USA)

Also Ranked

#69 on The Best Movies on Netflix Instant

#30 on The Best Comedy Movies on Netflix Instant

#1 on The Best Mumblecore Movies

#16 on 30+ Great Movies About Dating in Your 20s

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(500) Days of Summer is listed (or ranked) 6 on the list 20 Movies to Watch in Your 20s
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Audiences know right up front that the guy doesn't get the girl at the end of (500) Days of Summer. The non-linear, non-romance breaks the heart of narrator protagonist Tom (Joseph Gordon-Levitt), until the seasons change and Summer turns to Autumn. You can never be reminded enough that things will eventually get better after a break-up.

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Actors: Zooey Deschanel, Minka Kelly, Chloë Grace Moretz, Joseph Gordon-Levitt Matthew Gray Gubler, + more

Initial Release: 2009

Directed by: Marc Webb

Genres (Film): Drama, Romantic comedy

Tagline: Boy meets girl. Boy falls in love. Girl doesn't.

Rated: PG-13 (USA)

Also Ranked

#51 on List of Movies Like Inception

#34 on The Greatest Date Movies of All Time

#1 on The Best Movies About Getting Dumped

#13 on The Best Hipster Movies

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Garden State is listed (or ranked) 7 on the list 20 Movies to Watch in Your 20s
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Zach Braff's 2004 dramedy reminds audiences that maybe sometimes you can actually go home. When Andrew (Braff) heads from LA to Jersey for his mother's funeral, the alienated 26 year old reconnects with old friends and actually makes a few new ones. Andrew also finally confronts his father about the tragic events of the family's past.

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Actors: Natalie Portman, Jim Parsons, Ian Holm, Method Man Zach Braff, + more

Initial Release: 2004

Directed by: Zach Braff

Genres (Film): Romance Film, Coming of age, Drama, Comedy Comedy-drama, + more

Rated: R (USA)

Also Ranked

#39 on The Best Movies Directed by the Star

#94 on Movies with the Best Soundtracks

#85 on The Best Films Directed by Famous Actors

#27 on The Best Hipster Movies

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Almost Famous is listed (or ranked) 8 on the list 20 Movies to Watch in Your 20s
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The biggest life lessons always come with great risk. Take a chance - maybe you lose everything, maybe you come up roses. Almost Famous takes 16-year-old William (Patrick Fugit) on the rock and roll road trip of a lifetime. Along the way, his heart gets broken and his rock gods fail him. Even still, there's no chance he regrets a single second of the adventure.

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Actors: Zooey Deschanel, Kate Hudson, Anna Paquin, Jimmy Fallon Pauley Perrette, + more

Initial Release: 2000

Directed by: Cameron Crowe

Genres (Film): Music, Musical Drama, Musical, Drama Comedy, + more

Tagline: Experience it. Enjoy it. Just don't fall for it.

Rated: R (USA)

Also Ranked

#18 on The Best Movies "Loosely" Based on True Stories

#46 on The Greatest Soundtracks of All Time

#27 on The Best Movies About Writers

#58 on The Best Movies Roger Ebert Gave Four Stars

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