20-Something Movies To See by Your 20s

Now and Then

There are classic movies that each generation grows up with … and classic movies that just never go out of style. These are movies that every girl should have seen by their 20s. If you haven’t seen them yet then head out to Blockbuster or add them to your Netflix list immediately!

  1. Breakfast at Tiffany’s – Audrey Hepburn plays Holly Golightly, a New York socialite who finds romance with a new neighbor.  Holly’s Words of Wisdom: “You could always tell what kind of a person a man thinks you are by the earrings he gives you.”
  2. Casablanca – Another classic movie set in France during World War II. Rick Blaine (Humphrey Bogart) has to deal with his past when the love of his life comes to Casablanca. What did we learn from Rick? When it comes to a relationship, timing is everything and sometimes it’s just not the right time.
  3. The Breakfast Club – Arguably the best 80s movie! Five high school students land themselves in detention only to find that they may not be so different after all. We meet a lot of people in our 20s. Don’t automatically dismiss someone because they aren’t exactly like you. You could find a good friend!
  4. Pretty Woman – Edward picks up Vivian, a Hollywood Blvd. hooker and pays her to spend the weekend with him. Although it’s a fun, somewhat modern day Cinderella story, this is actually an example of some things that you should steer clear of in your 20s. It’s probably not the smartest idea to become a hooker. Also, little bit of advice… if a man is buying you clothing, the ball is definitely in his court and you will have no control.
  5. The Notebook – The biggest love story that hit theaters during our 20-something lives. Nicholas Sparks tells the story of Noah and Allie and how they were torn apart by her family only to find each other later in life.  Noah’s Words of Wisdom: “It’s going to be really hard; we’re gonna have to work at this every day, but I want to do that because I want you.”
  6. A Long Series – Okay, so you have options in this category. There are four acceptable series here that you should have at least seen one in full. Lord of The Rings, Star Wars, Harry Potter or Indiana Jones. We all grew up with different tastes in series of movies. So take your pick and have a movie marathon. Kudos if you have seen all of them! One of the great things about a long series is that when you are completely stressed out with your own life, you can use these series to escape the pressures of your 20-somethings and just relax.
  7. The Graduate – Here’s to you, Mrs. Robinson. Yes it’s important to have seen the movie where the guy sleeps with the mom and falls in love with the daughter. This movie is great for recent college grads because even though we have graduated it doesn’t mean that we have any clue about what we are going to do next. Most of us are in the same boat as Dustin Hoffman, and if you’re not, well it’s still a great movie.
  8. Monty Python and the Holy Grail – This is the best low-budget film ever made. It’s pointless, stupid and most of it doesn’t even make sense, but still a classic must-see movie. King Arthur and the Knights of the Round Table are on a quest for the Holy Grail. Everyone in their twenties is searching for something whether it’s love, work or figuring yourself out. Just like your own life, King Arthur is on a quest for something.
  9. Titanic – Jack and Rose meet on the infamous Titanic, fall in love and have to figure out how to stay alive when the boat hits the iceberg. Thankfully we aren’t actually dying on a ship, but aren’t we all trying to survive the uncertainty of our 20s?
  10. The Goonies – Chuck, Mouth, Data and Mikey go on an adventure to find some treasure left behind by “One-Eyed” Willy! Will they get to it before Fratelli family gets there first? If the Goonies taught us anything, it’s how important it is to work together as a team. Something all 20 somethings should learn when entering their careers.
  11. Tommy Boy – “Fat Guy in a little coat!” One of Chris Farley’s best roles as a break pad salesman who goes across the country with associate (Richard) David Spade to help keep Tommy’s dads company alive. Tommy learns how to change his behavior to try and sell break pads. Much like Tommy, 20-somethings have to learn how to sell themselves in order to get that first job they are trying to land and how to adjust to the company they are trying to work for.
  12. Forrest Gump – Tom Hanks plays one of the most lovable characters ever! Tom Hanks has had a million roles, but this is one of his most memorable performances. Forrest’s words of wisdom: “Life is like a box of chocolates, you never know what you’re gonna get.”
  13. An Adam Sandler comedy – There are many Adam Sandler comedies, but you have should have seen at least one of these two; Billy Madison or Happy Gilmore. Billy Madison has to go back to school in order to take over his dad’s hotel company and Happy Gilmore has to save his grandma’s house by joining a golf tournament. Take your pick. Just like Adam Sandler in both movies, 20-somethings have to prove that they can handle the responsibilities of post-college.
  14. Clueless – This is the Mean Girls of the 90s, so all you 20-somethings should have grown up with this movie. Cher and Dionne are the ultimate valley girls and also, Paul Rudd looks extra cute in this movie! Cher’s words of wisdom: “Sometimes you have to show a little skin. This reminds boys of being naked, and then they think of sex.”
  15. Butch Cassidy and The Sundance Kid – Besides having an awesome plot, there are two reasons to watch this movie and they are named Robert Redford and Paul Newman. They play bank robbers fleeing to Bolivia to hide from the law. Honestly, sometimes girls in their 20s just need to watch a movie with a couple of hot guys in it.
  16. Romy and Michelle’s High School Reunion – Best friends Romy and Michelle head out to Tucson to their 10th high school reunion and decide to act as businesswomen who invented Post-Its. Some of us are almost to the 10-year reunion mark and this movie definitely teaches you not to lie about where you are in life!
  17. Sleepless in Seattle – Before You’ve Got Mail, Tom Hanks and Meg Ryan starred in this movie together! After losing his wife and relocating to Seattle, Sam’s son calls into a local radio show to try and find his dad a new wife. Annie hears Sam’s story and instantly falls and love. Annie’s Words of wisdom: “Destiny is something we’ve invented because we can’t stand the fact that everything that happens is accidental.”
  18. Now and Then – Four best friends have the summer of their lives trying to figure out a murder. Flash-forward into the future and the four meet up and rekindle their friendship. Devon Sawa is the reason most of us watched this movie. Don’t lie, we know you thought he was super cute too. Crazy Pete’s advice that we can totally relate to: “Things will happen in your life that you can’t stop, but that’s no reason to shut out the world.”
  19. The Princess Bride – The movie includes everything you need for a classic fairytale, including, a fair maiden, a stable boy, a bad guy and some awesome swordfights. After being kidnapped can Buttercup, the princess bride, be rescued? What can you take away from this movie? Well, your life could always be worse. At least you are just trying to survive your 20s and aren’t trying to survive after being kidnapped!
  20. The Sandlot – If you have not seen this, sit down and really think about your childhood. This is the first movie you should rent out of the whole list if you have yet to see it! Baseball, best friends and some bullies too, this is a classic 90s movie and you don’t want to be the only 20-something in a group that doesn’t understand when someone says, “You’re killing me smalls.”

What movies would you add to the list of must see movies by your 20s?

Photo Credit: “Now and Then” New Line Cinema 1995

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  • Jordan

    i’d like to add any cameron crowe film (almost famous, say anything, jerry maguire, elizabethtown, etc.). all of these fils are essential for any 20 something trying to figure it all out.

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