2. Reality Bites (1994)
Reality Bites is all about that period of your twenties when you’re completely consumed with self doubt. Lelaina, played by Winona Ryder, wants to become a filmmaker, but has to deal with the harsh realities of being on her own. This film deals with that all too familiar notion of needing to find yourself before you can become what you’re meant to be.
On a related note, there’s an NBC reboot of the movie set to come to TV very soon… it’s the best/worst idea ever.
3. Lovely & Amazing (2001)
The Marks family is going through some seriously tough stuff: a mother in a health crisis, failing careers and marriages, insecurity, and having children. It tackles all of the hardships you’ll face as an adult, and will help you realize that image isn’t everything.
Plus, Jake Gyllenhaal is actually pretty cute in this one.
4. Before Sunrise (1995)
We all have that fantasy of traveling abroad and meeting a dashing stranger on a train, right? Well, that actually happens in Before Sunrise. It’s a movie that proves you should take every opportunity that comes your way, especially if that opportunity involves a day with Ethan Hawke. It also shows that you can meet someone when you’re least expecting it, and actually learn something from them. (Even if you don’t see them again for years afterward.)
5. Walking and Talking (1996)
Another Nicole Holofcener film, Walking and Talking is about two best friends — played by Anne Heche and Catherine Keener — living in New York City. Heche’s character is getting married, while Keener is dealing with the foibles of singledom. This movie is about finding happiness in yourself, and not relying on other people to make it for you.
6. 500 Days of Summer (2009)
Here’s the thing about this movie: It’s not a love story. Not really. It’s about a guy who’s stuck at a job he hates, because he’s afraid to take a risk and pursue his actual architecture dreams. That is, until he’s rejected by the girl of his dreams. Rejection is something we’ve all faced in our twenties, and that continues to be motivating even into adulthood.
7. Swingers (1996)
Mike just got out of a six-year relationship, and he’s having a hard time adjusting to single life. But after a trip to Vegas, and some L.A. bars, he starts to realize something: You’ll only find what you’re looking for when you agree to be yourself.
8. Scott Pilgrim vs. the World (2010)
Scott Pilgrim is forced to step out of his comfort zone and experience life in order to fight for his dream girl. If you blink, you might miss the message that even though staying comfortable is easy, the real victory comes when you go out and live your life.
9. Lola Versus (2012)
At least once in your twenties, everything will go to shit. Such is the case for Lola, as she suffers a nervous breakdown after her fiancé dumps her before their wedding. With the help of her friends, she attempts to rebuild her life, and realizes that the only way she can do that is if she learns how to stand on her own.
10. Garden State (2004)
This is a movie that a lot of people love to hate, mainly because of the whole Manic Pixie Dream Girl thing. And, ya know, other stuff. But at the heart of this film is the character of Andrew, who has done his best to numb himself to reality. When he goes back home for his mother’s funeral, though, he goes off of his antidepressants and starts to really face his past. In doing so, he’s able to move on and find happiness.
11. Going The Distance (2010)
OK, hear me out: This film is about Erin and Garrett, who wind up in an unlikely long-distance romance. They’re forced to decide how much it’s worth to them, and if they’re willing to sacrifice certain things to be together. It’s a situation that many twentysomethings find themselves facing, and it begs a valuable question: How far are you willing to go for someone you love?
12. The School of Rock (2003)
Poor Dewey Finn just wants to be a rockstar. (Don’t we all?) But when he’s kicked out of his band, he has to settle for plan B: filling in as a substitute teacher. This is a great film for anyone who’s questioning why they went into teaching. Yet the real takeaway from Dewey is that you can find your passion in unlikely ways.
13. Beaches (1988)
The great thing about Beaches is that you get to watch two best friends grow up together, from childhood into adulthood. You watch their twentysomething lives, as they live in a dumpy New York apartment, shift into their more stable thirties. This movie is perfect, because it reveals that life will throw out curveballs, no matter who you are. And even though bad things can happen, it doesn’t mean that good can’t come out of them. (Side note: You’ll weep through most of this film.)
14. The Wood (1999)
Much like Beaches, we get to see a few stages of life hurdles from the three best friends. First during their teen years, and the second stage as Taye Diggs’ character gets ready for his wedding day. When he gets cold feet, it’s up to his best friends to snap him out of it, and force him to look ahead instead of constantly looking back.
15. St. Elmo’s Fire (1985)
Post-Georgetown angst is the game of this film. Whether it’s dealing with sex, the lackluster job market, or dealing with other people’s expectations of what you should be. The lesson you take away is that at some point, you have to move on from college life so you can enter into adulthood.
16. Good Will Hunting (1997)
Oh poor, stubborn, genius Will. He thinks he’s soooo smahhht, with his apples, and writing on chalkboards. That is, until Robin Williams basically sets him straight: Book smart is one thing, actually experiencing life is another. Will is forced to face his past and present, even though it’s painful. But in doing so, he’s able to move forward and go see about a girl. Pretty good life lessons here, folks.
17. About Schmidt (2002)
Jack Nicholson is arguably his best in About Schmidt, which follows the story of a retired insurance actuary as he begins to question whether or not he’s made a dent in the world. This movie is especially great as you inch closer to 30, and start to wonder how you’ll affect the world, and what you want your legacy to be.
18. Harold and Maude (1971)
Harold is obsessed with death, and dying, and funerals. Until he meets Maude, and then he starts to live his life with a little more hope. She teaches him a lesson in the importance of living life to the fullest, something we could all use a little of in our twenties.
19. Waiting to Exhale (1995)
When you sacrifice yourself, some bad things can happen, or so we learn in Waiting to Exhale. This story about four friends whose lives are turned upside down in their thirties almost serves as a cautionary tale. Give up your ambitions, and it may come back to haunt you. Stay stuck in the same spot emotionally and you’ll get left behind. The list goes on, and all of it is wonderful.
20. Romy and Michele’s High School Reunion (1997)
The problem with going to your 10-year high school reunion, is that everyone expects you to be the person you were in high school. But what we learn from Romy and Michele, is that growing up means you let go of worrying about what other people think, and embrace who you really are. (An awesome fashion designer with great dance moves.)
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