20 Must-Watch Summertime Movies (Part 2)

Discover the best movies that take place during summer with part 2 of our list of summertime movies to watch over break.

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Must watch summer movies part 2

It’s summer, and we all finally have a little free time on our hands. Last Thursday, we wrote about ten fun summer movies to watch over break, and this week we’re going to finish that list.

Like we mentioned last time, some of these movies explicitly happen over summer break, while others just have a distinct summertime vibe. However, they all have a fun nostalgic feel that will make you want to grab a snow cone and hit the beach.

Let’s get right to it!

11. Dazed and Confused

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Alright, alright, alright – you all knew this one was coming!

Dazed and Confused tells the story of high school students (well, except Wooderson – aka Matthew McConaughey) on the last day of school who kick off the summer by celebrating their new senior or freshman status. There’s not too much of a storyline, but that’s actually what I love about this movie – it reminds me of the aimless nights I had with my friends, driving around and casually bumping into other friends from school at popular hangouts.

Favorite Moment: “You gotta keep livin’ man, L-I-V-I-N”

12. Caddyshack

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If you haven’t seen Caddyshack, I’m not sure if we can be friends. Okay, I guess we can be friends as long as you rent this movie and watch it like, tonight.

Caddyshack tells the story of a country club and everyone connected to it, from the rich old owner to a young and slick playboy, to the teenage caddies to the cooky groundsmen. It features an all-star cast and some of the biggest comedians of the decade, including Chevy Chase, Bill Murray, and Rodney Dangerfield.

Caddyshack is the perfect movie to watch with a summer fling. Your date will think you’re super cool for suggesting such a classic comedy, and you’ll both laugh the whole night through.

Favorite Moment: I’ll never forget the ol’ Baby Ruth bar in the pool scene.

13. Can’t Hardly Wait

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When this movie was developed, the writers and producers agreed that the best part of teen comedies in the ’80s took place during party scenes, so they decided to set Can’t Hardly Wait almost exclusively at a graduation party! It features several different high school stereotypes, and has multiple storylines that all intertwine with one another.

Another cool thing about this movie is that it features several celebrities of the ’90s before they were super-famous, including Jennifer Love Hewitt, Peter Facinelli, and Seth Green. Plus, it’s now on Netflix. You can’t beat that!

Favorite Moment: When each main character in the ensemble cast is introduced, a graphic (that looks just like an old yearbook bio) pops up and gives you vital stats on each character. Hey, it was a pretty creative way to tell everyone’s story!

14. National Lampoon’s Vacation

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Wanting to spend some quality time with his family, Chevy Chase takes his family on a cross-country trip to visit the Walley World amusement park. Of course, disaster ensues.

National Lampoon’s Vacation was based on a short story by John Hughes, directed by Harold Ramis, and starred Chevy Chase, Anthony Michael Hall, and John Candy – all major ’80s powerhouses. It’s one of those movies that TNT or TBS plays frequently, so I have lots of memories watching it at the lake with my family while rubbing aloe on my shoulders and trying to keep from napping. It’s a total classic.

Favorite Moment: Walley World under duress. It’s too epic.

15. The Sisterhood of the Traveling Pants

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I still remember catching a matinee show of this movie in theaters with all of my best girlfriends. The Sisterhood of the Traveling Pants is about four best friends who are all doing very different things with their summer vacations. They stay in touch throughout the summer by writing letters and passing around a pair of jeans that miraculously fits them all.

I love this movie for two reasons. First, it introduced me to Blake Lively, who I absolutely love. Second, the fashion in it is SO dated – puka shell necklaces, flared jeans, pastel polos, and peasant shirts galore. The early 2000s fabulous is sure to bring a smile to your face.

Favorite Moment: Any scene with that foxy soccer coach or adorable Grecian guy. Rawr!

16. Grown Ups

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Grown Ups tells the story of five best friends who reunite for a holiday weekend at the lake after their middle school championship basketball coach passes away. As the weekend progresses, they learn that even though they’re all married with children and now face adult problems, they’re still a bunch of goofy big kids at heart.

I wouldn’t exactly call this flick a cinematic masterpiece or anything. It relies pretty heavily on gross-out and screwball gags, and is made up of a weird mix of kid jokes and adult humor. That being said, if you grew up on Adam Sandler comedies, you know exactly what to expect – and this movie totally delivers.

It’s kind of the perfect movie to watch while you organize your bedroom, surf on Pinterest, or sit around and catch up with old friends. Full of easy laughs.

Favorite Moment: At the end of the movie, the five men face off against the same team that they beat thirty years ago during their middle school basketball championship. Not gonna lie, the ending is pretty heartwarming.

17. Sleepover

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Alexa Vega stars in this coming-of-age comedy about four girls who take on the popular clique at school, vying for rights to eat lunch by the water fountain with all the other cool kids. Throughout the night, they’re chased by a pack of teen skateboarders; Steve Carrell, who plays a security guard; and Jane Lynch, who plays Vega’s mom.

Yes, I realize the above description makes Sleepover sound… errr, a liiiiiittle questionable. And yes, there are several things that happen in this movie that just aren’t possible (I mean, most 14-year-olds I know don’t set up internet dates at nightclubs or have a SmartCar available to drive).

That said, I remember being around the same age as the girls when this movie came out, and it does a great job capturing the awkward, exciting, and awesome time that is summer break when you’re a teen. I have fond memories of my sister and I watching this movie together and laughing at how corny the film was (but also secretly enjoying it!).

Favorite Moment: When the girls give their dorky teacher a quick makeover and help him get a date at the night club. It was cute, okay!?

18. Independence Day

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Anyone else remember seeing Independence Day and being just freakin’ terrified? This blockbuster epic was one of Will Smith’s first flicks, and helped him break away from his young Fresh Prince image. And as we all know, this film helped Will Smith kick start one of the most prolific action movie careers of our era.

Something else that’s notable about this movie is how awed we were by the special effect when it first came out – and how outdated they are when we watch it today. Check out the attack scene, even if it’s just on YouTube – you’ll be shocked at how silly it looks!

Favorite Moment: “President” Bill Pullman’s epic speech. I get cold chills just thinking about it!

19. Jaws

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When it comes to classic thrillers, Jaws might be one of the most quintessential. I’ve lived in landlocked Oklahoma my entire life, but after seeing this movie on TNT one afternoon, I was terrified to water ski in the lake. Yes, you read that right. The lake. I was a child full of irrational fears.

Favorite Moment: “We’re gonna need a bigger boat.”

20. Empire Records

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Confession: I was a bit of a skater girl in my teen years. Not that I actually skated or anything – no, I was much more interested in skater boys than I was in skateboards. I remember going to the skate shop once a week or so on the pretense of buying t-shirts, CDs, or pieces of flair, but I was actually there to flirt with the boys on the half pipe out front. Unfortunately, I usually was not very successful.

Empire Records captures the carefree, wild, and exciting feel of summers hanging out with, well, a crowd you know your parents wouldn’t approve of. Liv Tyler is absolutely stunning in this movie, and it’s fun seeing Rory Cochrane in a movie with several similarities to the one we all know and love him for: Dazed and Confused.

Favorite Moment: Three words: Roof Dance Party


Did you favorite make this list? What are some of your favorite summertime movies? Have you seen any of the movies on this list? What’s on your list of movies to catch over the summer? Leave a comment and tell us what you think!

4 thoughts on “20 Must-Watch Summertime Movies (Part 2)”

  1. To save other girls some time, I’m pretty sure I checked every single one and NONE are available for streaming on Netflix. Ugh.

    • Thanks for checking Meredith! Sorry these aren’t available – Netflix Instant seems so random with the titles it includes and it’s always annoying. (My dream is to give up the DVD portion of my subscription someday…) Maybe we need to do another post with only Streaming-available titles!

  2. A young(er) Evan Peters is in your #17 pick, Sleepover. Kind of cool since he’s in X Men: Days of Future Past that’s in theaters now! And of course American Horror Story if anyone watches that!


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