13 Movies You Loved As A Teenager But Are Too Cynical To Enjoy Now

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The late ’90s/early 2000s were a grand time for movies, especially for those of us who are now well into our twenties.  Romance!  Comedy!  Drama!  A middle-aged man running a Woodstock-style camp alone for a bunch of kids with no parental supervision!  So many makeovers for Ugly Duckling Girls!  Regardless of the premise, we loved them all.  And we still watch them when they’re featured on cable television channels at 12 a.m.  But we have a different perspective now – we’re grown-ups (that phrase brought to you by A Grain of Salt).  So it’s harder to enjoy some of these movies knowing what we know now, that we didn’t know back when we thought the sun rose and set on high school drama and Lip Smackers.

While there are a few kids’ movies that adults can enjoy, these are my picks for some of the more outlandish plots of yesteryear that seemed totally kosher back then, but have me scratching my head in anxious worry and finely-honed cynicism now.  Feel free to add your own suggestions in the comments!

1. She’s All That

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We all swooned over Freddie Prinze Jr. once upon a time, and sighed plenty of “awws” over the “dramatic” transformation of Laney Boggs.  But between the synchronized/choreographed dance number at the prom and how not-ugly-at-all Laney was to begin with, it’s hard to sit through this without rolling your eyes now. Admit it.

2. Never Been Kissed

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Okay. COME ON.  Josie Grossie wasn’t fooling anyone into thinking she was actually 17 years old in this, right? That would be like me rolling up to my old high school and being all “I’d like to enroll” and no one suspecting a thing.  I HAVE CROW’S FEET. And don’t even get me started on David Arquette as “Mr. Rob”.

3. A Walk To Remember

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This is super realistic and heartfelt in the land of NOPE.  I’ve already opined on how much I think this movie destroyed the book for me (I was a cynical teen but not so cynical that I didn’t read Nicholas Sparks books at the time), but it’s just like… no one looks that beautiful when they’re dying, Mandy Moore.  And Shane West is about as hooligan-ish as a teddy bear.

4. Save The Last Dance

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Maybe I’m biased because I can’t tolerate Julia Stiles in anything (okay, maybe a little bit in 10 Things I Hate About You).  But this movie is ridiculous.  It’s actually hard to sit through on the Sunday afternoons it plays on TBS.  I love Kerry Washington as the “oh hell naw” stereotyped older sister, though.

5. Ferris Bueller’s Day Off

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While hilarious and still one of my favorite movies, there’s no way this could happen.  Not even back in the Middle Ages of the 1980s.  The jig would have been up for me the second I feigned illness – Mr. and Mrs. Bueller acted like Ferris had the Black Plague yet they still went to work? No.

6. Any Adam Sandler Movie

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They’re all so stupid. So. Stupid. And yet I get sucked in, time after time, when Billy Madison is on because I loved it so much back in high school.  Even if I’m dumber for having watched it.

7. Don’t Tell Mom The Babysitter’s Dead

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Words cannot describe how much I love this movie, so basically I’m calling myself a liar because I still enjoy it.  It’s just so far-fetched and ridiculous to take seriously. Whose mom goes away to AUSTRALIA for an entire summer, doesn’t tell them they’re getting a babysitter, hires an elderly woman she’s never met to watch the kids, and doesn’t really care when she never hears from any of them for months?  Not to mention Sue Ellen’s resume falsification could land her in serious legal trouble, but whatever.  I’M RIGHT ON TOP OF THAT, ROSE.

 8. Drop Dead Fred

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Creepy, hilarious, traumatizing, totally inappropriate for kids… this movie nails all of the above.  But I’ll try not to be too much of a Snotface when I say if my parents had even an inkling that I had an imaginary friend as a grown woman, I would undoubtedly be committed.  RIP Rik Mayall, though.  Respect.

9. Cruel Intentions

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Filthy rich step-siblings carrying on a carnal affair alone in a Park Avenue penthouse apartment, snorting blow and plotting the virgin sacrifice of an innocent Reese Witherspoon? Totally realistic.  Selma Blair’s sloppy, clueless, clumsy Celeste clearly had some sort of developmental disability, and Sebastian and Kathryn just poked fun at her. So rude.

10. Coyote Ugly

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I used to get so mad when the soundtrack for this movie skipped in my portable CD player, ugh. Look, props to any movie that offers Tyra Banks a role (albeit a microscopic one), as a former bartender I now know there’s nothing, NO-THING, glamorous about it.

11. The Prince & Me

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I might have to take this one back, because we’re living in a time where things like “I Wanna Marry Harry” exist.  But could you imagine Prine William enrolling in your college and flying totally under the radar, scrubbing dishes and falling in love with you? Answer: yes, yes you could.  When you were 14.

12. What A Girl Wants

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As a mild Anglophile myself, I can appreciate the whole American-girl-in-London thing, but really?  You’re telling me Colin Firth–British Politician Living In Downton Abbey–didn’t know about his daughter?  And totally forgave Kelly Preston’s hippie ass just like that even though she hid it?  And Amanda Bynes is capable of opening the eyes of an entire aristocracy to her Casual Free Spirit American Ways?  Cringe.

13. Camp Nowhere

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Sweet baby Jesus but I loved me some Jonathan Jackson and Andrew Keegan back in my BOP magazine days.  This movie was so awesome to Young Me because it was a bunch of kids living Woodstock-style (co-ed, too, OH MY GOD YES) for an entire summer with Christopher Lloyd.  Now I know it’s ridiculously criminal and disturbing for a middle-aged single man to “run” a fake camp for several unsupervised children all by himself.

(Lead GIF: Tumblr)

You can reach this post's author, Cassandra Hough, on twitter.
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