It’s May, and graduation is upon us! That’s right – the moment you’ve been waiting for (or dreading) your entire high school or college career has finally arrived.


And while graduates should be slipping into reveries of summer fun and boundless possibility, graduation often proves more stressful than the exams and papers proceeding it. There are uncomfortable family gatherings to coordinate, parties to throw and…oh, you know…just figuring out what the hell you’re going to be doing with the rest of your life (panicking yet?).


Though many of you may be rushing to your computers to put the finishing touches on your resume, preparing for job interviews or just succumbing to your latest nervous breakdown, 20to30 wants to remind you of all there is to be excited about during this time in your life!


So, we’ve prepared a countdown of 8 of our favorite classic graduation movies to remind you of why you should be so thrilled…albeit a bit nostalgic…now that school has finally come to an end.


8. The Girl Next Door (2004)


The quintessential nerd fantasy


A Georgetown-bound high school senior seems to have it all – the perfect GPA, more college admissions than he can handle and a bright future in politics. However, Matthew (Emile Hirsch) is a virgin. He’s never had a girlfriend and tragically spends all his time studying or with his equally geeky friends. That is until blonde hottie Danielle (Elisha Cuthbert) moves in next door…


Though not exactly high-brow cinema, we still love The Girl Next Door for its mix of raunchy R-rated humor and coming-of-age sentimentality. This is the ultimate film for those high school and college nerds who fear that they spent too much time studying and planning for the future and not enough time living in the moment.


7. Can’t Hardly Wait (1998)


Who could forget Jennifer Love Hewitt as prom queen Amanda Beckett in this ‘90s cult-classic?


The film revolves around the events of a high school graduation party, where Preston (Ethan Embry) plans to proclaim his undying love to his high school crush Amanda Beckett (Jennifer Love Hewitt). The timing seems perfect. School is over, there’s nothing to lose and Amanda has just broken things off with her jock boyfriend. But here’s the catch – Preston has never even spoken to Amanda and nearly faints at the sight of her.


We love this film for its unabashedly cliched, but loveable characters and well…for ‘90s Jennifer Love Hewitt in that blue tank top (drool…). What shy, nice-guy didn’t have an Amanda Beckett of their own in high school or college?


6. She’s All That (1999)


Another late-‘90s classic!


Big man on campus Zack (Freddie Prinze, Jr.) is inexplicably dumped by his cheerleader girlfriend, Taylor, mere weeks before they are to be crowned king and queen at the senior prom. Zack plans revenge and proclaims that any girl could take Taylor’s spot as prom queen with the right look and boyfriend. Zack bets his skeptical jock friends that he can turn art-geek Laney (Rachael Leigh Cook) into the high school prom queen with as little as a makeover and him on her arm.


Like Can’t Hardly Wait, She’s All That is another cliched rom-com with an unusually attractive cast (since when do American high schools all look like Abercrombie and Fitch adverts?). But, we can’t help but find ourselves rooting for the love between Zack and Laney and swooning over Freddy Prinze (just wait for the soccer ball scene at the end). She’s All That also reminds us of the petty hardships of prom dates, choosing colleges and navigating high school cliques that made high school…well, high school…


5. Say Anything (1989)


’80s throwback!


High school slacker Lloyd (John Cusack) pursues class valedictorian Diane (Ione Skye) shortly after high school graduation before Diane is to leave to study in England. Diane falls for Lloyd after his persistence impresses her, and the two begin a summer romance despite Diane’s grudgingly disapproving father.


We not only love this film for the ’80s soundtrack and wardrobes but for its charm. Doesn’t that iconic boombox scene just warm your heart? Our hearts, however, break knowing that Diane is soon to leave for England. This film makes us appreciate our friends and loved ones before we have to say our graduation goodbyes.


4. Grease (1978)


Grease lightning! There’s no reason for you not to have seen the film that continues to inspire Halloween costumes and has “You’re the One That I Want’ forever stuck in our heads.


During the 1958-1959 school year, summer lovers Danny (John Travolta) and Sandy (Olivia Newton-John) are unexpectedly reunited when they realize they are enrolled in the same high school. However, Danny is torn between maintaining his badboy, womanizing image and being the sensitive lover he once was to Sandy.


While the over-the-top ’50s hairdos and infectious music numbers may not remind us of our final high school days, the love story between Danny and Sandy calls to mind the butterflies we had for our high school sweethearts. This is a love story for the ages!


3. American Pie (1999)


It’s a common realization for the soon-to-be high school graduate… I’m about to move out of my childhood home, live on my own, do my own laundry and…OH MY GOD I’M STILL A VIRGIN!


This late-‘90s blockbuster, which forever changed the way we look at apple pie, is the story of four high school seniors who each pledge to lose their virginity by prom night. Their increasingly desperate attempts grow more and more hilarious, with Jim (Jason Biggs) pursuing a seemingly-innocent-turned-sexual-maniac band geek (Alyson Hannigan), and Paul (Eddie Kaye Thomas) going after a classmate’s mom (Jennifer Coolidge). Oh yeah, there’s also an ‘incident’ with an apple pie somewhere in between…


While high school was a seminal time of arduous schoolwork and growing experiences, a lot of us also just really wanted to get laid… It is for the shamelessly straightforward but ultimately honest approach of American Pie that makes it such a must-see!


2. Legally Blonde (2001)


The film that taught us both basic legal jargon and the ‘bend-and-snap’ (works every time)


Sorority-girl and fashion merchandising major Elle Woods (Reese Witherspoon) pursues ex-boyfriend Warner (Matthew Davis) to Harvard Law School with the intent of winning him back – and no ambition whatsoever of actually becoming a lawyer. Elle, in an endlessly optimistic effort to prove herself to her ex-boyfriend, studies hard enough to win an internship with one of their professors. Here, she oversees a major murder trial and lends her unique, sprightly perspective to law.


Following college graduation, we all feel a bit stupid. We don’t yet know how to properly navigate the real world, find employment and begin the phase of our lives known as ‘adulthood.’ We all are kind of like dumb, airheaded blondes during this time in our lives. We have good intentions, though we don’t always pursue them in the best of ways. And that’s what makes Legally Blonde so relatable.


1. The Graduate (1967)


What else would we have chosen as our number 1? This classic not only gave us the seductive, enigmatic figure Mrs. Robinson but also made cougars mainstream. Very ahead of its time!


The Graduate is the story of Benjamin Braddock (Dustin Hoffman), a recent college graduate aimlessly wandering through life. Along the way, Benjamin is seduced by an older woman, Mrs. Robinson (Anne Bancroft) before eventually falling for her daughter Elaine (Katharine Ross).


Despite its titillating and controversial premise, The Graduate is, at its core, a tale of wrestling between childhood and exciting yet daunting newfound adulthood. While we admire this film for breaking boundaries, we mostly love it for its truthful depiction of the post-grad struggle.



Thomas Freeman is Texas-transplant and aspiring journalist trying (but often failing) to navigate New York City. A current NYU student, Thomas also writes articles and manages media content for 20to30.

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