Film 20 Movies to Watch in Your 20s  

Ann Casano
46.3k views 20 items
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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
Photo: via Imgur
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.

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

Initial Release: 1994

Directed by: Ben Stiller

Also Ranked

#19 on Movies Turning 25 in 2019

#39 on The Best Movies of 1994

#75 on Movies with the Best Soundtracks

#72 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
Photo: via Imgur
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?

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

Initial Release: 1999

Directed by: David Fincher

Also Ranked

#7 on The Best Psychological Thrillers of All Time

#34 on The Most Rewatchable Movies

#2 on Movies Turning 20 in 2019

#16 on The Best Movies Based on Books

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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.

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

Initial Release: 1989

Directed by: Spike Lee

Also Ranked

#76 on Movies Turning 30 in 2019

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

#21 on The Best Movies of 1989

#29 on The Best Movies Directed by the Star

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Eternal Sunshine of the Spotle... is listed (or ranked) 4 on the list 20 Movies to Watch in Your 20s
Photo: via Wikimedia
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.

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

Initial Release: 2004

Directed by: Michel Gondry

Also Ranked

#64 on The Best Psychological Thrillers of All Time

#21 on The Greatest Date Movies of All Time

#84 on The Biggest Tearjerker Movies of All Time

#89 on Movies That Should Be Made Into Broadway Musicals

see more on Eternal Sunshine of the Spotless Mind